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The Official Saastr Podcast: SaaS | Founders | Investors on Smash Notes

The Official Saastr Podcast: SaaS | Founders | Investors podcast.

December 28, 2019

The Official Saastr Podcast is the latest and greatest from the world of Saastr, interviewing the most prominent operators and investors to discover their tips, tactics and strategies to attain success in the fiercely competitive world of SaaS. On the side of the operators, we centre around getting from $0 to $100m ARR faster, what it takes to scale successfully and what are the core elements of hiring. As for the investors, we learn what metrics they hone in on when examining SaaS business, what type of metrics excites them and what they look for in SaaS founders.



Episodes with Smash Notes

Neha Sampat is the Founder and CEO @ Contentstack, a modern content management system bringing business and tech teams together to deliver personalised, omnichannel experiences. Atypical in our world, but Neha scaled the business to well over $1M in ARR before raising funding. Now Neha has raised over $31M from the likes of Insight Partners and Illuminate. Prior to Contentstack, Neha was the Founder and CEO @ Built.io and before that spent 10 years as the Founder and CEO @ Raw Engineering, building a leading digital transformation consultancy.

 In Today’s Episode We Discuss:

  • How did Neha make her way into the world of SaaS and content management systems having previously built a digital transformation agency?
  • How the heck did Neha scaled Contentstack to over $1M in ARR without raising capital, whilst being based in the Bay? What were the signals that made Neha realise she had a scalable software business? What did Neha look for in her first seed round investors? How did that profile change when she went out to raise the Series A?  
  • How has being a sommelier helped Neha break the glass ceiling of business? What are some lessons Neha has learned in terms of build true and genuine relationships with customers beyond the transaction? What are the counter-intuitive strategies Neha has found works when it comes to motivating remote teams?
  • Why did Neha decide to build out so much of the tech team well outside of the Bay in a town outside of Mumbai? Does Neha believe the future of tech is in the valley or decentralised?  

Neha’s 60 Second SaaStr:

  1. Neha’s biggest strength and biggest weakness as a leader?
  2. What does Neha believe that many around her do not?
  3. The biggest obstacle to the success Neha has achieved?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Neha Sampat

Startups can get messy. Especially in growth. David Sacks (Yammer, PayPal) shares how to navigate from 50-500 employees.

Kurt Muehmel is the Chief Customer Officer @ Dataiku, the platform democratizing access to data and enabling enterprises to build their own path to AI in a human-centric way. To date, the company has raised over $146M in funding from some of the best in the business including ICONIQ, Firstmark, Battery Ventures and CapitalG to name a few. As for Kurt, he joined the company over 5 years ago and has risen from AE to VP EMEA to VP Sales Engineering to today as Chief Customer Officer. Before Dataiku, Kurt spent 5 years at Deloitte as a Manager advising primarily European public authorities on sustainable development policies.

 In Today’s Episode We Discuss:

  • How Kurt made his way into the world of enterprise SaaS with Dataiku having started his career at Deloitte in Paris?
  • What does it take to go from 0-1 in implementing both AI and data science disciplines in 20th-century companies? Where do many go wrong with their first steps? How can one assist them in the right way? How does Kurt feel about services revenue? At what stage or ratio does it become too much? 
  • How does Kurt approach the challenge of change management? What does great change management look like? Where do so many go wrong? How can content be used to efficiently scale change management practices? How does one need to engage different teams for effective change management? 
  • How does Kurt think about the right pricing mechanism for the customer today? How does one find a mechanism that does not disincentivize the customer with usage? How does Kurt feel about discounting? To what extent is Kurt and Dataiku willing to engage with pilots and POCs? Where do many go wrong here? 

Kurt’s 60 Second SaaStr:

  1. Biggest challenge of Kurt’s role with Dataiku today?
  2. What does Kurt know now that he wishes he had known when he entered the world of SaaS?
  3. Who does Kurt look up to in the world of customer experience? Why?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Kurt Muehmel

Ready to hire your first VP Sales?  But haven’t done it before? SaaStr CEO, Jason Lemkin shares his interview checklist. 

Aileen Lee is a U.S. seed investor. A venture capital investor, she is the founder of Cowboy Ventures. Lee coined the often-used Silicon Valley term unicorn in a TechCrunch article "Welcome To The Unicorn Club: Learning from Billion-Dollar Startups."

In this episode of the SaaStr podcast, Aileen and SaaStr Founder Jason Lemkin take a deep dive on how Aileen finds deals, her tips for a winning pitch, and the state of VC in 2020. 

Julie Herendeen is the CMO @ PagerDuty, the real-time operations platform ensuring less downtime and fewer outages, meaning happier customers and more productive teams. Prior to their IPO in 2019 PagerDuty raised funding from some of the best in the business including Accel, a16z, Baseline, Bessemer and Harrison Metal to name a few. As for Julie, prior to PagerDuty she was Vice President of Global Marketing @ Dropbox. Before Dropbox Julie was CMO @ Lookout and before Lookout, Julie enjoyed VP roles at both Yahoo and Shutterfly. If that was not enough, alongside her role at PagerDuty today Julie is also an angel with Broadway Angels and a Board Member @ Hubspot. 

 In Today’s Episode We Discuss:

  • How Julie made her way from the world of consumer into the world of enterprise and came to be CMO @ PagerDuty today? What were some of Julie’s biggest lessons from her time as VP Global Marketing at Dropbox?
  • Does Julie believe that marketing should be held accountable to a number tied directly to revenue? How does Julie believe sales and marketing should work in unison? How can sales be involved in pipeline generation meetings? Should AEs make themselves responsible for sourcing new leads also? What does the ideal handoff look like? 
  • How does Julie see the best marketing and product teams working together? What can marketing do to collect the most valuable data to inform product decisions? In what forum should they be relayed to product teams? How should product and marketing leaders interact most efficiently? 
  • How does Julie think about the relationship of customer success and marketing? Does Julie agree that with the increasing amount of marketing content used post-sale, marketing is doing much of the work of CS? Where does Julie see many going wrong when investing heavily into thought leadership and content marketing?

Julie’s 60 Second SaaStr:

  1. Which marketing leader does Julie most respect and why?
  2. What would Julie most like to change about the world of SaaS today?
  3. What is the optimal relationship between the CEO and the CMO?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Julie Herendeen

Given that so many VC pitches are over Zoom now, we thought it would be worth sharing the things it’s easy to get wrong when pitching investors.

Pitching VCs is like anything.  You’ll get better at it over time.  Later, you’ll even get great at it.  Once you know how it works, it’s not even that hard to knock it out of the park.

But until then, so many founders make unforced errors.   Rookie errors.  Here are 16 that you can easily avoid / fix right now today.

On today's episode, Christoph shares his five tips for fundraising during a pandemic. 

  1. Have a clear COVID-19 assessment 
  2. Start with an extra-long "long list"
  3. Disqualify ruthlessly
  4. Have a killer deck 
  5. Build trust remotely 

Christoph has invested in more than 20 SaaS startups and lives and breathes SaaS, everything from “A as in AI-enhanced B2B software” to “Z as in Zendesk”. Christoph co-founded Point Nine Capital in 2011.

Before that, he co-founded two Internet startups (DealPilot.com in 1997 and Pageflakes in 2005). In 2008 he became an angel investor and discovered Zendesk, Clio, FreeAgent – and his love for SaaS.

On this episode of the SaaStr podcast, our CEO, Jason Lemkin, chats with Zapier CEO, Wade Foster, on Distributed Teams and Building a Cloud Product.

Zapier is a global remote company that allows end-users to integrate the web applications they use. Although Zapier is based in Sunnyvale, California, it employs a workforce of 250 employees located around the United States and in 23 other countries.

David Politis is the Founder & CEO @ BetterCloud, the company that helps IT discover, manage and secure the digital workplace. To date, David has raised over $186M in funding with BetterCloud from the likes of Accel, Warburg Pincus, Greycroft, Flybridge and Dropbox to name a few. Before founding BetterCloud, David was an early employee of Cloud Sherpas (acquired by Accenture), where he led the company to become the leading cloud services partner to SMB worldwide. Prior to Cloud Sherpas, David was a founding employee and General Manager of Vocalocity (acquired by Vonage), which he grew into one of the top providers of cloud PBX technology.

 In Today’s Episode We Discuss:

  • How David made his way into the world of SaaS and came to found BetterCloud? How has David seen the rate of cloud adoption within enterprise over the last 5 years? Has it been faster or slower than he thought? 
  • People often suggest operators are suited to certain stages of a company lifecycle, does David agree with this? What are the leading indicators an individual is struggling to scale? How does one communicate that to them effectively? How does David think about the decision to move an individual to another role vs release them? 
  • What does radical transparency really mean to David? How does the ability to have radical transparency within your org change when the org is 10 people vs 100 people? What are the biggest challenges of scaling transparency? From a meeting structure view, what can leaders do to encourage transparency? 
  • How does David feel about the method of OKR setting? How has his mindset changed towards OKRs? What does the decision-making process look like for deciding which OKRs to focus on? What OKRs do they focus on at BetterCloud? How does one know when they need to change their OKRs?

David’s 60 Second SaaStr:

  1. What would David most like to change in the world of SaaS?
  2. How has David seen himself emerge and develop as a leader?
  3. What is the biggest challenge of David’s role within BetterCloud today?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

David Politis

Mark Suster is a managing partner at Upfront Ventures, the largest venture capital firm in Los Angeles, and a prominent blogger in the startup venture capital world.

In this episode of the SaaStr podcast, he shares his learnings on the current landscape of funding in the time of Coronavirus, including:

  • Valuation and compression 
  • Forecasting market trends
  • The slowdown in VC
  • His best advice for surviving the downturn and raising a round of funding 

Michael Katz is the Founder & CEO @ mParticle, the customer data platform for brands leading the customer data revolution with clients from Airbnb to Spotify to Postmates. To date Michael has raised over $120m in funding with mParticle from GV, Social Capital, Greylock, Bain Capital Ventures and a friend of the show in Zach Coelius. Prior to founding mParticle, Mike was the Founder & CEO @ Interclick, where he organically grew revenue to over $140m in 5 years. The company went public in 2009 and was acquired by Yahoo in 2012 for $270m, a 50% premium on existing share price. If that was not enough, Michael is also on the board of Brightline and a mentor with Techstars.

 In Today’s Episode We Discuss:

  • How Michael made his way into the world of SaaS and enterprise SaaS having founded and IPO’d an adtech business previously?
  • Why did Michael make the move to CRO 8 months ago? How does Mike think about when is the right time to hire your first CRO? How does this hire correlate to your hiring in sales enablement? What are the different CRO profiles Mike has seen? How does Mike advise founders on those that work best for early-stage?
  • Why does Mike believe that playbooks are for suckers? What is the reasoning for the reductionism towards the power of the playbook? How does Mike think about the relationship between playbooks and predictability? 
  • How does Mike make sales data really actionable within the company? What is the right way for founders to do post-mortems on won and lost deals? What is the right way to structure their sales pipeline? Who should be involved in analysing this data? What can be done to incentivize sales to be accurate in their sales data?
  • Why does Michael believe that most sales meetings are unproductive? What is the right way to structure your sales meeting? Who should be brought into the meeting other than the sales team? How does Michael advise sales reps to maintain customer relationships post-sale? Where do many go wrong here? 

Michael’s 60 Second SaaStr:

  1. What would Michael most like to change about the world of SaaS?
  2. What is the hardest element of Michael’s role today with mParticle?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Michael Katz

These are unique times. In some ways, we can use our playbooks, make adjustments, and in other ways, things are very different. What isn’t likely to be very different is that recurring revenue … recurs. This is the bedrock of SaaS.

Hear how Slack CEO, Stewart Butterfield, is adapting to change and his advice on how to take care of your team and customers. 

Christine Trodella is Head of Americas for Facebook’s Workplace product, the communication tool that connects everyone in your company, through Groups, Chat, Rooms and Live video broadcasting. Prior to Workplace, Christine was Head of America’s for Facebook’s Audience Network and before that spent 5 years as a Group Director across multiple different sales and account teams within Facebook’s mid-market channel. Before Facebook, Christine was an Executive Director @ WebMD and before that spent close to 3 years in media sales at Yahoo. 

 In Today’s Episode We Discuss:

  • How Christine made her way into the world of SaaS as part of a non-SaaS company and how that led to her leading Americas for Workplace by Facebook?
  • What have been the biggest benefits of scaling a SaaS company within a non-SaaS company? What are the biggest challenges or misalignments of scaling Workplace within Facebook? What have been some of the core and early mistakes the team made in their strategy to build out the Workplace sales and marketing machine? 
  • What have been Christine’s biggest lessons on what it takes to sell really effectively to some of the largest enterprises in the world? What do CIO’s most want in pricing? How does Christine think about the pricing problem of having a variable pricing mechanism without disincentivizing usage? How does Christine think about and approach discounting?
  • Does Christine believe remote is the new normal? What really interesting data have Christine and the Workplace team seen since the world has move to work from home? How has behaviour changed on the platform with the rise of remote work? 

Christine’s 60 Second SaaStr:

  1. What would Christine most like to change in the world of SaaS?
  2. When I say success, who is the first person that comes to Christine’s mind?
  3. What is the biggest challenge of Christine’s role within FB today?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Christine Trodella

Leveraging survey data from 66+ enterprise SaaS companies, Matt Garratt, Managing Partner of Salesforce Ventures shares the landscape of how businesses are shifting their sales & GTM strategies to react to today's uncertain times. Adnan Chaudhry, SVP of Sales at Salesforce then provides actionable takeaways on how to refocus your sales teams, engage with customers, adjust your sales comp and how you can properly forecast in today's new landscape.

David Spinks is the Founder @ CMX Media, the premier network for community professionals. In 2019, CMX was acquired by Bevy, where David now serves as the VP of Community. Bevy is the leading provider of in-person community software, powering community programs at companies like Slack, Twitch, Salesforce, Atlassian, and Duolingo. Prior to CMX, David founded 2 prior startups centred around different forms of community building and before that was Community Managerin the early days of LeWeb the largest tech/startup conference in Europe.

 In Today’s Episode We Discuss:

  • How David made his way into the world of SaaS and came to found CMX? Why David believes that community is so central for all SaaS companies today?
  • How does David advise teams on expectation setting around virtual events? How ambitious should they be? What big mistakes does David often see in the early days of the planning? How does this differ if you have an existing cohort of users vs are starting new with no audience?  
  • How dependent is the success of the community on the platform it is hosted on? What is the ideal size for Slack, Telegram and Whatsapp communities? Should the host seed the discussion or allow it to be natural? How important is it to establish a handbook of expected actions and behaviours? Should you cull members who are inactive? 
  • What does David believe separates good from great when it comes to discussion groups? What innovative strategies has David seen work when it comes to bringing a virtual event to life? What is the right amount of people in that discussion group? What is the core role of the moderator for the group?

David’s 60 Second SaaStr:

  1. Biggest misconception around virtual events?
  2. Virtual events: Permanent tide change or purely in the COVID world?
  3. What has been David’s favourite virtual event? Why?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

David Spinks

Hear from Michelle Zatlyn, co-founder and COO of Cloudflare. Michelle started the company during an economic downturn in 2009. Now, Cloudflare runs one of the world's largest networks that helps make the Internet more secure, fast, and reliable, with a market cap of more than $6B. Despite the challenges of uncertainty, money not flowing, and a generally dark mood, she was able to do it and learned a lot along the way. In this talk, Michelle will share how she made her business idea come to life and some lessons learned that can help other entrepreneurs—from solving a real, meaningful problem, to communicating in a crisis, prioritizing when there's a true lack of resources, and more.

Bridget Gleason is the Head of Sales and Customer Success @ Tidelift, the company providing managed open source, backed by maintainers. Tidelift has raised over $40M from some of the best in the business including Foundry Group and General Catalyst. As for Bridget, she has the most incredible track record. Before Tidelift, Bridget was VP of Sales @ Logz.io and before that was VP of Corporate Sales @ Sumo Logic where she drove ARR up by a record 237%. Prior to SumoLogic, Bridget was VP of Sales @ YesWare where she increased MRR per rep by 450%. Finally, before YesWare, she was VP of Sales @ Engine Yard, where she tripled monthly recurring revenue, over the course of her 3+ year tenure, in 3 key leadership roles.

 In Today’s Episode We Discuss:

  • How Bridget made her way into the world of SaaS and Sales and came to be Head of both Sales and Customer Success at Tidelift?
  • Why does Bridget believe the best starting point for customer success is “company culture and value”? How does company culture impact the quality of customer success? In practice, what can one do to improve it? Who has done this well? How does value drive customer success forward? 
  • How does Bridget think Maslow's Hierarchy of Needs drives the roadmap for customer success? What core elements does it change? Where do most teams go wrong in implementing the role out of their CS strategy? When should one hire their first CS rep? What should that hire look like from an experience perspective?
  • How does Bridget advise her CS reps the best ways for them to build trust with their clients? What works? What does not work? Does Bridget believe CS teams should be involved in the upsell process? Does that endanger the element of trust?

Bridget’s 60 Second SaaStr:

  1. What does Bridget know now that she wishes she had known when she entered the world of SaaS?
  2. What would bridget most like to change about the world of SaaS today?
  3. What is the most challenging element of Bridget’s role with Tidelift?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Bridget Gleason

Prepare for the worst, hope for the best. Hear from Garry Tan, co-founder and managing partner at Initialized Capital, about how to protect your business during a crisis. He'll cover remote work, team management, sales, marketing, product development and more.

Jessica Lin is a Co-Founder and General Partner @ Work-Bench, one of New York’s leading early-stage enterprise funds with a portfolio including the likes of Cockroach Labs, X.ai, Dialpad, VTS and Catalyst to name a few. Prior to Work-Bench, Jessica was a Learning and Development Manager at Cisco Systems, where she worked with the Engineering organization on Agile transformation, innovation and culture. Jessica is actively involved with the education and workforce development community in New York City and as chair of the Industry Advisory Board at Opportunities for a Better Tomorrow.

 In Today’s Episode We Discuss:

  • How Jessica made her way from learning Swahili into the world of enterprise and into the world of venture with the founding of Work-Bench?
  • How should founders expect to see their new business pipe be impacted by COVID? What does Jessica believe is the right way to do proper pipe reviews? What specific elements does Jessica really double click on in reviews? Where does Jessica find managers and founders do pipe reviews wrong?
  • What does Jessica believe is the right way for sales reps to engage with new customers during this time? What is the right tone to adopt that achieves both empathy and a business objective? How should sales teams and CS respond to requests for discounts? What should be the compromise with discounts? 
  • What specific and deliberate things can startups do not just to prevent churn but also to increase usage and upsell? Does Jessica agree with the rule of thumb that in enterprise, on an annual basis, 95% of your customers should retain? What other strategies has Jessica seen work really well for retention?

Jessica’s 60 Second SaaStr:

  1. What would Jessica most like to change about the world of SaaS?
  2. What is the hardest element of Jessica’s role today with Work-Bench?
  3. The NYC ecosystem, pros and cons?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Jessica Lin 

The true test of marketers. Are you a revenue driver or a cost center? You cannot afford to be the latter. Marketing leaders must focus their teams on the areas that will drive revenue while they cut costs - the biggest impact for the business. Join TripActions CMO Meagen Eisenberg at SaaStr Summit as she highlights her approach to ensuring Marketing delivers on its mission-critical role even in times of uncertainty or crisis.

Navin Chaddha is the Managing Director @ Mayfield who just last month announced $750M in new funds split across their core and select funds. As for Navin, under his leadership Mayfield has raised over $2.2Bn in new funds and he has backed some of the best of the last decade including Poshmark, Lyft, Hashicorp, CloudGenix and more. During his career Navin has invested in 50 companies, 17 have gone public, 20 have been acquired. Prior to VC, Navin was an entrepreneur where he co-founded or led 3 startups, all of which had successful exits with one being acquired by Microsoft. 

 In Today’s Episode We Discuss:

  • How did Navin make his way into the world of venture from successfully founding and exiting 3 businesses? What made him take the jump into investing full-time from being an EiR?
  • How does Navin expect the B2B landscape to be impacted by COVID-19? How does Navin advise B2B founders to think about how renewals will be impacted? How does Navin advise founders to think through how to approach the topic of discounting with their customers? In what situations does Navin agree to provide discounts to customers?
  • How does Navin foresee the B2C landscape to be impacted? How does Navin advise founders to think through the level of aggression with which they pursue traditional marketing channels, now with much lower CACs? Will these CACs remain low priced? How does Navin expect company pricing to change over the next few months?
  • How has Navin seen himself evolve and change as a board member over the last decade? What have been his major moments of learning? What advice would he give to new board members joining their first boards? What can board members do to build a relationship of trust and intimacy with their founders? What works? What does not?

Navin’s 60 Second SaaStr:

  1. What does Navin know now that he wishes he had known when he entered the world of venture with Mayfield in 2004?
  2. What is the hardest element of Navin’s role with Mayfield today?
  3. What would Navin most like to change about the world of venture? Why?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Navin Chaddha

Romain Lapeyre is CEO of Gorgias. Gorgias is the leading help center on the Shopify platform, and that gives them a pulse into a large segment of SMBs in particular. They have almost 2,500 customers in segments both struggling (fashion, luxury), and growing (electronics, etc.). They are coming up on $10m ARR but aren’t there quite yet, so a lot like a lot of you, or where you’ll be soon enough.

John Mellor is Chief Strategy Officer @ Domo, the company that allows you to leverage BI at scale to empower your team with data. Prior to their IPO, Domom raised funding from the likes of Benchmark, Founders Fund, a16, Greylock and IVP to name a few. As for John, prior to Domo he served as vice president for strategy and business operations for Adobe’s Digital Experience business, driving more than $3 billion in annual revenue. John joined Adobe through the company’s acquisition of Omniture in 2009, where he served as executive vice president of marketing, driving all marketing efforts to strategically advance the industry’s largest standalone web analytics business.

 In Today’s Episode We Discuss:

  • How did John make his way into the world of SaaS over 2 decades ago and how did that lead to his running a $3Bn ARR business line at Adobe and lead to his joining Domo? What were John’s biggest takeaways from his decade at Adobe?
  • Why does John believe that COVID will be a bigger accelerant than any other C-level led initiative? For vendors going through that digital transformation with their customers, what is the right tone to adopt that is both empathetic and achieves business objectives? Is digital transformation a technology challenge or a behavioural challenge?
  • How will a 100% virtual event environment impact physical events when and if they do come back? What were John’s biggest takeaways from running Domo’s annual event virtually? What worked? What did not work? On a conversion basis, how did it compare to in-person events? How should we structure content for these virtual events?
  • How does John think about the role of leadership in a crisis such as this? What is the right tone for the leader to adopt? Where does John believe many leadership teams go wrong in times such as this? How can leadership teams ensure that a crisis is not self-fulfilling and how can one prevent that mindset?      

John’s 60 Second SaaStr:

  1. What does John know now that he wishes he had known when he entered the world of SaaS?
  2. What is the optimal relationship between the CEO and Chief Strategy Officer?
  3. What would John most like to change about the world of SaaS 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

John Mellor

Gusto's Lexi Reese walks you through scaling high performance teams. Is trust earned or given? How do you communicate for impact?

Carolyn Guss is VP of Corporate Marketing @ PagerDuty, the company keeping your digital operations running perfectly with their real-time operations platform. Prior to their IPO in April 2019, PagerDuty had raised funding from some of the best in the business including a16, Bessemer, Meritech, Harrison Metal and Elad Gil to name a few. As for Carolynn, prior to joining PagerDuty she spent 5 years as the GM of Method Communications San Francisco Office and before that spent time on the other side of the pond with a close to 7-year stint at Orange as Head of Corporate PR and Head of US Communications.

 In Today’s Episode We Discuss:

  • How Carolynn made her way across the pond from Head of US Communications at Orange to GM of Method in SF to then playing a key role in the marketing team at PagerDuty?
  • How does Carolynn think startups and larger companies can replace the leads that are lost from having no events in a COVID world? How are PagerDuty shifting their strategy? How does PagerDuty think about brand marketing? Does it have to be tied to a number directly tied to revenue? What are the challenges with brand marketing?
  • What does Carolynn believe is the right tone to approach customers within this time? How can one be supportive but also drive towards business objectives? In terms of tone, what is the right tone to approach the broader team with? How does PagerDuty gain a sense of company morale at scale? What tools do they use?   
  • How does Carolynn think about the benefits of transparency both with employees and with customers? Is there an extent to the benefits of transparency? Can one ever been too transparent? How does one think about this in a very corporate perspective with PagerDuty now being a public company?      

Carolynn’s 60 Second SaaStr:

  1. What does Carolynn know now that she wishes she had known at the beginning of her time in marketing?
  2. Hardest element of her role with PagerDuty today?
  3. Who is killing it in the world of SaaS marketing? Why? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Carolynn Guss

Join SaaStr CEO Jason Lemkin and Bessemer Venture Partners Partner Byron Deeter for a deep dive on what's going on in Venture Capital and Cloud with one of the leading investors in the space, Byron Deeter of Bessemer Venture Partners.

Bhavin Shah is the Founder & CEO @ Moveworks, the cloud-based AI platform, purpose-built for large enterprises, that resolves employees' IT support issues⁠—instantly and automatically. To date Bhavin has raised over $XM with Moveworks from the likes of Mamoon Hamid @ Kleiner Perkins, Arij Janmohamed @ Lightspeed, Bain Capital, Sapphire Ventures and ICONIQ. Prior to Moveworks, Bhavin was the Founder and CEO @ Refresh which was later acquired by LinkedIn and then before that founded Gazillion Entertainment, a company he scaled to over 30 employees. 

 In Today’s Episode We Discuss:

  • How Bhavin made his way into the wonderful world of SaaS and came to found Moveworks?
  • What are the core challenges IT teams are facing as a result of the move to remote work? Where do many make mistakes here? What can one do from a structural perspective to set them up for success when moving to remote? 
  • What does great change management look like in Bhavin’s mind today? Where do so many go wrong here? How does this change in the world of remote? Who should be involved in executing on the change management plan?  
  • How does Bhavin think about the role of customer success today? Why does Bhavin believe that customer success and product should be in one org? How does Bhavin think about the interplay of marketing and customer success? Is marketing moving closer and closer to customer success with their content?      

Bhavin’s 60 Second SaaStr:

  1. What is the hardest element of Bhavin’s role with Moveworks today?
  2. Hardest role to hire for today? Why? 
  3. If Bhavin could change one thing in the world of SaaS today, what would it be?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Bhavin Shah

Many people make the false assumption that the path for a highly successful SaaS company is straight “up and to the right”. Of course, for those involved, the reality of the journey is characterized by a series of obstacles that must be navigated. Fmr. Shasta Ventures Doug Pepper will share the key challenges that were overcome to allow Marketo to become a $5B SaaS Category Leader in Marketing Automation.

Anthony Kennada is the CMO @ Front, the startup that provides your team with better email so they can treat every customer like your only customer. To date, Front have raised over $138M from some leading names including Sequoia, Eric Yuan @ Zoom, Ryan and Jared Smith @ Qualtrics, Michael Cannon-Brookes and Jay Simmons @ Atlassian and Frederic Kerrest @ Okta to name a few. As for Anthony, prior to Front Anthony was the founding CMO at Gainsight where he and his team are credited with creating the Customer Success category. At Gainsight Anthony and the team developed a new playbook for B2B marketing that fueled the company’s growth from $0 to over $100M of ARR. If that was not enough, Anthony is also the author of Category Creation: How to Build a Brand that Customers, Employees, and Investors Will Love. The book debuted as a number one new release on Amazon.

In Today’s Episode We Discuss:

  • How Anthony made his way into the world of SaaS starting in the sales team at Box and how that led to his entering the world of marketing and creating the customer success category?
  • How does Anthony marketing playbook change when making the move from Gainsight with higher ACV’s and longer sales cycles to Front with lowers ACV’s and much higher volume? How does Anthony think about ABM today with Front given the lower ACVs? At what ticket size does ABM make sense?
  • How does Anthony feel about brand marketing? Why did Anthony and Front decide now was the right time to engage with billboards? How does Anthony think about data and tracking for brand marketing? Does Anthony believe that all marketing has to be tied to a number directly related to revenue?  
  • How does Anthony seeing a changing relationship between customer success and marketing? How is marketing being pushed further into the realms of CS? What is the optimal relationship between CS and marketing? How does this compare to the relationship of sales and marketing more traditionally?       

Anthony’s 60 Second SaaStr:

  1. What does Anthony know now that he wishes he had known at the beginning of his time in marketing?
  2. What is the hardest element of Anthony’s role with Front today?
  3. Who does Anthony think is killing it in the world of marketing today?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Anthony Kennada

We’re obviously in a very unique situation today. The pace at which Corona is impacting us all right now is so fast, it’s hard to keep up.

Today is different from other times but in SaaS, it will probably be like ’08-’09 downturn — just faster.

Join Jason Lemkin, CEO and Founder of SaaStr, and Nick Mehta, CEO of Gainsight, as they take a look back at what happened to them as a SaaS vendor in ’08-’09, and what learnings you can leverage.

May Habib is the Founder & CEO @ Qordoba, the platform that helps everyone at your company write with the same style, terminology and voice. To date, May has raised over $21M in funding with Qordoba from the likes of Upfront Ventures, Aspect Ventures, Bonfire Ventures and Michael Stoppelman to name a few. Before entering the world of SaaS, May was a vice president at one of the world's largest sovereign wealth funds, where she was the first employee on the technology investment team, building a portfolio now worth over $20B. Before that, May started her career in the New York Office of Lehmann Brothers raising capital for software companies.  

In Today’s Episode We Discuss:

  • How May made her way into the world of startups and SaaS from being a VP at one of the world’s largest sovereign wealth funds in the Middle East?
  • How does May think about and assess operational survival in times of such uncertainty? Why does this downturn feel so different to prior downturns? Operationally, what needs to fundamentally change about your processes?
  • How does May think about when is the right time to engage with pre-emptive burn cuts? Where does one look first in the organisation when making these cuts? How does one structure those discussions? What is the right way to do it? What is the right way to communicate the cuts to the team, customers and investors? 
  • How does one keep the existing teams spirits high when they have just seen many of their friends be released? What is the right way to manage those discussions? What can founders do to build unity in their team now everyone is WFH? What has worked well for the Qordoba team? Where do many go wrong here?       

May’s 60 Second SaaStr:

  1. What is the most challenging element of May’s role with Qordoba today?
  2. What does May know now that she wishes she had known at the beginning?
  3. If May could change one thing about the world of SaaS, what would it be and why?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

May Habib

The first step in success with SMB clients is to recognize that it’s not a one size fits all scenario. Companies need a specialized approach for SMB accounts, different than the tactics used for Enterprise. Andrei Brasoveanu will sit down for a conversation with Agnes Bazin Doctolib on how to create a targeted and effective sales process tailor-made for SMB.

Rachel Hepworth is VP of Marketing @ Pilot, the startup that offers the best bookkeeping, tax and CFO services for growing businesses. To date they have raised over $58M from some of the best in the business including Index Ventures, John Collison, Paul English, Drew Houston, Frederic Kerrest, Diane Greene and more incredible names. As for Rachel, prior to joining Pilot, she saw the hyper-growth of Slack firsthand enjoying a couple of different roles including Head of Growth Marketing and then also Head of Self Service and Platform Marketing. Before Slack, Rachel spent 4 years at LinkedIn where she led the product marketing team for content experiences. Finally, before LinkedIn, Rachel spent close to 3 years at Climate Corporation, prior to their $1Bn exit to Monsanto. 

 In Today’s Episode We Discuss:

  • How Rachel made her way from marketing manager at Climate Corporation to VP of marketing at Pilot today? What were Rachel’s biggest takeaways from her time seeing the hyper-growth at Slack?
  • How does Rachel think about organic growth and inciting word of mouth today? How does Rachel think they can be more accurately tracked and measured? How does Rachel think about the optimal ratio of paid to organic in growth? Would Rachel agree in paid, your payback period doubles every $5M you spend?
  • With the rise of product-led growth, are we seeing a fundamental shift in the structure of sales and marketing? How does Rachel see marketing move ever close to the function of customer success today? What is the optimal way for customer success and marketing to work together? 
  • How does Rachel think about the importance of getting in front of your customers? Why does Rachel believe that data tells you the what and customer conversations tell you the why? What is the right way to structure your customer conversations? Where do so many people go wrong here?      

Rachel’s 60 Second SaaStr:

  1. Hardest element of your role with Pilot today?
  2. If Rachel could change one thing about SaaS today, what would it be?
  3. Who is killing it in SaaS marketing? Why?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Rachel Hepworth

The startup journey moves in waves—whether you’re ready or not. After finding funding and product/market fit, your next steps as a founder in the hypergrowth phase can determine the future of your company. Harry Stebbings of Stride.VC and Robert Vis of MessageBird will walk through lessons learned to survive hypergrowth and what will make a difference when it comes to scaling. Hear how to navigate fast growth and how to look ahead as you travel forward.

Harry Hurst is the Co-Founder & Co-CEO @ Pipe, the startup that gives you control of your cash flow by giving you access to the full annual value of your monthly subscriptions, upfront. This month they announced their $6M seed round led by David Saks @ Craft and joined by Fika, Weekend Fund, Naval Ravikant and WorkLife Ventures to name a few. Prior to Pipe, Harry co-founded Skurt raising over $11M in the process before being acquired by Fair.com. Harry has also angel invested in the likes of BreathePod and Try.com. 

 In Today’s Episode We Discuss:

  • How Harry made his way from the UK to founding one of Silicon Valley’s hottest SaaS startups with the founding of Pipe?
  • How does Harry think about when is the right time for a startup to raise VC funding? How does Harry stress test the alignment between the founder and the VC/ Opposingly, when is the right time for a founder to take non-dilutive capital from Pipe instead?
  • Pipe’s lending model is so centred around churn prediction, what does their churn analysis look like at Pipe? How does Harry think about the right way to structure churn post mortems? Why does Harry believe investing in customer success is far more important than customer acquisition? 
  • How does Harry think about the importance of brand for enterprise startups today? Do you have to invest in it from Day 1? What mistakes does Harry see many founders make when it comes to investing in their early brand?      

Harry’s 60 Second SaaStr:

  1. What does Harry know that he wishes he had known at the beginning?
  2. What does Harry believe is the hardest role to hire for today? Why?
  3. What does Harry believe that most around his disbelieve?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Harry Hurst

According to a study from SiriusDecisions, the majority of buyers (81%) today make purchase decisions based on buying experience, over product or price. To meet buyers’ high expectations and manage the challenging sales landscape, companies must involve their entire organization in maturing the sales process- including after prospects sign on the dotted line. This session will outline a practical approach to growing revenue and retention by aligning sales, marketing, and customer success.

Today we deep dive into what startups can learn from the large SaaS incumbents of today. 

 

Sarah Varni: CMO @ Twilio on her biggest takeaways from her time at Salesforce.

 

Erica Schultz: President of Field Operations @ Confluent on her biggest takeaways from her time at Oracle.

 

Whitney Bouck: COO @ Hellosign on her biggest takeaways from her time at Box.

 

Leyla Seka: Partner @ Operator Collective on her biggest takeaways from her time at Salesforce.

 

Ryan Bonicci: CMO @ G2 on his biggest takeaways from his time at Salesforce.

 

Tien Tzuo: Founder & CEO @ Zuora on his biggest takeaways from his time at Salesforce.

 

Jaleh Rezai: Founder & CEO @ Mutiny on her biggest takeaways from her time at Gusto.

 

Eugenio Pace: Founder & CEO @ Auth0 on his biggest takeaways from his time at Microsoft.

 

Mark Goldberg: Partner @ Index on his biggest takeaways from his time at Dropbox.

 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Starting a company can be daunting, exhausting, and expensive, but with the right focus and idea - extremely rewarding; take it from Andrew Filev, Founder and CEO of Wrike. In this session, he will outline the do's and dont's that he learned bootstrapping Wrike. Where it makes sense to invest your precious resources when to outsource, and how to save yourself money without cutting corners.

Karl Sun is the Founder & CEO @ LucidChart, a visual workspace that combines diagramming, data visualization, and collaboration to accelerate understanding and drive innovation. To date, Karl has raised $114M with LucidChart from some of the best in the business including K9 Ventures, Meritech, Iconiq, GV and Kickstart in Utah. As for Karl, prior to founding the company he spent 6 years at Google in some fascinating roles including Head of Patents, Head of Business Development in China and running Google’s energy investments. As a result of his success, Karl was recently announced as EY’s Entrepreneur of the Year. 

 In Today’s Episode We Discuss:

  • How Karl made his way into the world of SaaS with the founding of LucidChart having been Head of Business Development for Google in China and Head of Patents?
  • How does one know when we need to hire generalists vs specialists? How does this requirement change as the company scales? How does Karl fundamentally think about finding great talent and keeping top of funnel full? How does Karl think about working with recruiters? What works? What does not work?
  • Karl has been in every interview for every new hire for the first 6 years of the business, why? How does Karl think about doing this at scale? How does Karl structure the hiring process today? Why do they have a hiring committee? What does the process look like? How do they assess and test for culture?  
  • How does Karl think about retaining agility and flexibility with scale? How does Karl maintain employee empowerment with the implementation of process? How does Karl think about the balance between creating accountability without a fear of failure? What are the challenges of this?     

Karl’s 60 Second SaaStr:

  1. What is the hardest role to hire for today? Why?
  2. Hardest element of karl’s role as CEO today? Why?
  3. What does Karl know now that he wishes he had known at the founding of the company?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Karl Sun

SaaStr CEO Jason Lemkin and EZPR Founder Ed Zitron sit down to talk about all things PR. Who actually gets into these outlets? Is PR just pitching and getting articles? Take a listen for more.

David Skok is a General Partner @ Matrix Partners, the firm with a portfolio including the likes of Hubspot, ZenDesk, Quora, CloudBees and more incredible companies. As for David, he started his first company in 1977 aged just 22. Since then David has founded a total of four separate companies and performed one turn-around. Three of these companies went public. David then joined Matrix from SilverStream Software, which he founded in June 1996. Prior to its July 2002 acquisition by Novell, SilverStream was a public company that had reached a revenue run rate in excess of $100M, with approximately 800 employees and offices in more than 20 countries around the world. David is also the author of foreentrepreneurs.com the must read blog in the world of SaaS metrics. 

 In Today’s Episode We Discuss:

  • How David made his way into the world of SaaS at the age of 22? How David went from founding 3 public companies to entering the world of venture with Matrix? Does David agree, “entrepreneurship does not get easier with time, it just gets different”?
  • What does David believe is the crucial step missing in B@B when it comes to finding product market fit? What is the most common mistake B2B companies make in the hunt for PMF? How should founders think about budget and resource allocation in this search for PMF? When is to early to measure unit economics and CAC?
  • How does David think about scaling sales teams? How does one know when is the right time to hire your first sales reps? What content and learnings should you have in place when you make the hire? How does David think about payback period on a per rep basis? What have been his lessons on optimising payback period for sales reps?  
  • What numbers is David looking for when it comes to payback period? Why is 12 months so crucial? How should founders think about sales rep compensation? What have been David’s learnings on how to integrate sales and marketing so tightly? How does marketing and customer success intertwine to be successful?     

David’s 60 Second SaaStr:

  1. Who is the best board member David has sat on a board with? Why?
  2. What advice would David have for me having just joined my first board?
  3. What would David most like to change about the world of tech and SaaS today?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

David Skok

RevenueCat is managing tens of millions of dollars in mobile subscriptions and growing 20% a month. Most of us think a lot about standard b2b and Cloud subscriptions, but we’re still new to the issues, challenges and opportunities in mobile subscriptions.

Jaleh Rezaei is the Founder & CEO @ Mutiny, the startup that allows you to personalise your website for each and every visitor. Jaleh has raised from some of the best in the early stage business with Mutiny including the likes of Y Combinator, Uncork Capital and Cowboy Ventures on the fund side and then Mathilde @ Front, Henrique @ Brex and Shan-Lyn Ma @ Zola on the operator side. Prior to founding Mutiny, Jaleh spent an incredible 4 years at Gusto seeing their hypergrowth first hand as one of the first 10 employees. If that was not enough, Jaleh has also enjoyed advisory roles at both Google and Y Combinator. 

In Today’s Episode We Discuss:

  • How Jaleh made her way into the world of SaaS as one of the first team members at Gusto and how that led to her founding Mutiny most recently? 
  • What were Jaleh’s biggest takeaways from her time at Gusto? How did that time impact her operating mentality with Mutiny today? How did her time at Gusto teach her about the right way to build company culture? Where do so many go wrong with this?
  • What does Jaleh believe is the biggest problem in SaaS marketing today? How does Jaleh specifically use ABM to acquire customers and leads effectively? What price points is required for an ABM strategy to be viable?  
  • How does Jaleh approach the issue of determining the success of marketing? Should marketing be held accountable to a number tied directly to revenue? How does brand marketing play into this? Where are the nuances here?     

Jaleh’s 60 Second SaaStr:

  1. What is the hardest role to hire for today?
  2. Hardest element for Jaleh of her role with Mutiny today?
  3. What does Jaleh know now that she wishes she had known when she entered the world of SaaS?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Jaleh Rezaei

Join Bessemer Venture Partners' Alex Ferrara as he takes a look at trends and predictions for the cloud industry in 2019. One of the most popular sessions from SaaStr Annual, this presentation will provide an in-depth look at the cloud computing industry across Europe and globally.

Karen Page is a General Partner @ B Capital Group with a portfolio including the likes of Bird, Branch, Fishbrain, Hollar and MachineMax to name a few. Prior to joining the world of venture, Karen was a Senior Director at Apple and before Apple, Karen spent an incredible 9 years at Box where she was responsible for defining and leading Box's Industry GTM strategy. Plus, from 2007 until 2013, Karen ran all of Box's business development, partnership, and strategic alliance activities. If that was not enough, Karen is also on the board of some incredible companies including Deputy and Plastiq. 

In Today’s Episode We Discuss:

  • How Karen made her way into the world of SaaS as one of the first employees at Box and then how that led to her transition to the world of investing with B Capital? 
  • What were Karen's biggest takeaways from seeing the hyper-scaling at Box? How did helping Aaron raise the Series B and onwards inform her view of what it takes to raise funding from the best SaaS investors? How does Karen think her mindset will shift when making the move from angel to now institutionally investing with B Capital?
  • When does Karen think is the right time for startups to think about partnerships? What questions should they ask in the “dating” phase of a potential partnership? What are the red flags? Does Karen agree that signing a massive partner too early can be dangerous? What does Karen recommend in terms of getting in front of the best CIOs? 
  • Is Karen concerned by the compression of fundraising timelines? How does Karen meet entrepreneurs before they go out to raise? How does Karen advise founders when it comes to the question of whether they should always be raising or not?     

Karen’s 60 Second SaaStr:

  1. What does Karen know now that she wishes she had known entering the SaaS industry?
  2. What is Karen’s favourite book? Why?
  3. Can a partnership be too big too early for a startup?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Karen Page 

If your SaaS business has a sales team, there’s no way to grow 100% year-over-year without also growing your sales leadership. In this talk, CircleCI VP of Revenue Jane Kim will talk about the 5 mistakes all new sales leaders make. Knowing the common pitfalls won’t stop you or your team from making them, but it will help build the most important skill any manager can have: resiliency. Come and learn how to build great leaders so you can grow your team, and ultimately, your business.

Eugenio Pace is the Founder & CEO @ Auth0, the startup that allows you to rapidly integrate authentication and authorization for web, mobile, and legacy applications so you can focus on your core business. To date, Eugenio has raised over $213m with Auth0 from some of the best in the business including Meritech, Sapphire, Manu Kumar @ K9, Bessemer and Trinity. Prior to founding Auth0, Eugenio spent an incredible 12 years at Microsoft leading the Program Management team in the patterns & practices group at Microsoft.

In Today’s Episode We Discuss:

  • How Eugenio made his way into the world of startups with the founding of Auth0? What were his biggest takeaways from 12 years watching the hyper-growth of Microsoft first hand? 
  • How does being a developer-first product fundamentally change the go-to-market? Who has done this best over the last few years? What have they done that has allowed them to scale faster than others? What has been Eugenio’s takeaways in what works when building developer communities and early developer adoption?
  • How does Eugenio respond to the common thinking that “devs don’t have the budget”? Does this limit your ability to expand into large ACVs once in an organisation? How does Eugenio approach the issue of agency when selling to CIOs but having devs use the product? 
  • What have been Eugenio’s biggest lessons in what it takes to make a freemium product successful? How does one know how much of the secret sauce to giveaway? How does Eugenio approach pricing today through 4 different variables? How does Eugenio adopt a variable pricing mechanism that does not discourage usage?     

Eugenio’s 60 Second SaaStr:

  1. Quality or quantity of logos in the early days?
  2. What does Eugenio know now that he wishes he had known at the beginning of his time at Auth0?
  3. What is the hardest element of his role today as CEO? What is he doing to really upscale there? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Eugenio Pace

Customer expectations are at an all-time high, making it more and more difficult for companies to please them. Companies who understand their customers well are the ones who rise to the top over their competitors. New Relic, provider of real-time insights for software-driven businesses has this formula figured out. Hear from Roger Scott, New Relic's EVP and Chief Customer Officer as he shares his 7 tips and tricks for keeping your customers happy— and how to do so at a large scale.

Dimitri Sirota is the Founder & CEO @ BigID, the startup that provides advanced data discovery and intelligence for the data centre and cloud. To date Dimitri has raised over $145M for BigID from some of the best in the world of enterprise including Boldstart, Scale Venture Partners, Bessemer, Salesforce Ventures and Tiger Global who just a couple of weeks ago, led their latest $50M Series C. Before to BigID, Dimitri founded 2 prior businesses, the first in 1999 being a VPN security company called eTunnels and then the second being Layer Technologies where Dimitri enjoyed an incredible 10 year journey leading to their acquisition by CA Technologies in 2013. Dimitri is also an angel investor with a portfolio including Zume Pizza, Modalyst and TalentClick. 

In Today’s Episode We Discuss:

  • How Dimitri made his way into the world of enterprise software and came to found BigID as his third company? 
  • What specifically would Dimitri advise founders when the interests of their investor are not aligned to theirs? What is the right way to manage that situation? Does Dimitri believe that founders should always be raising? Does Dimitri believe when the money is on the table, you should take it? What is the right way for founders to think about valuation? 
  • What did the fundraising journey look like for BigID? What situation does every founder want to put themselves in? How does Dimitri think about runway and using fundraising for optionality? What does Dimitri make of the rise of pre-emptive rounds? How does Dimitri determine when is the right time to pour fuel on the fire?     

Dimitri's 60 Second SaaStr:

  1. What is his biggest strength and biggest weakness as a CEO?
  2. Who was the first check in BigID? How did the check come about?
  3. What does Dimitri believe that most around his disbelieve? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Dimitri Sirota

When it comes to seamlessly scaling your applications, a top-notch engineering team will be your foundation. Next comes the decisions to build or buy your infrastructure, DNS, monitoring, and analytics tools. Julian Lemoine, Co-Founder, and CTO of Algolia will share his lessons learned on how to stay focused and innovative as you scale while also avoiding the innovation for innovation’s sake pitfalls.

Yousuf Khan is the Chief Information Officer @ Automation Anywhere, the only web-based and cloud-native RPA platform. To date, Automation Anywhere has raised over $840m in financing from Salesforce Ventures, Workday, General Atlantic and NEA to name a few. Prior to Automation Anywhere, Yousuf was the CIO & VP of Customer Success @ Moveworks. During his time at the company, they raised over $108m from Lightspeed, ICONIQ, Kleiner, Sapphire and Bain Capital. Before Moveworks, Yousuf was CIO @ Pure Storage during their period of hypergrowth both as a private and public company. Finally, before Pure, Yousuf’s first role in the valley was with Qualys again as CIO where he owned the entire global IT budget.   

In Today’s Episode We Discuss:

  • How Yousuf made his way from the UK to the valley and how that led to his becoming one of the leading CIOs today in the rising prominence of CIOs in enterprise? 
  • What are the biggest green lights for CIO’s when startups are pitching them? Why does Yousuf believe now more than ever, the buyer experience is more important than the price? What makes for the best buyer experience for the CIO? What are the biggest red flags CIOs see when startups are pitching them? What must startups always remember when pitching CIOs?
  • How does Yousuf advise CIOs to approach pricing strategy when pitching CIOs? WHat must startups remember about how CIOs think about price? What other elements of the contract should startups really spend a lot of time focusing on? Where do founders make mistakes in negotiation? What can they do to enforce a sense of urgency when signing new clients?  
  • What can startups do to actively work with procurement teams and make the process as fast as possible? How does Yousuf advise founders to think about customised procurement requests to fit certain buyers? What do CIOs really want to see in the form of security and compliance? How can startups clearly and articulately present their plans for security, compliance and change management?     

Yousuf’s 60 Second SaaStr:

  1. Who does Yousuf think is killing it in the world of CIO’s today? Why?
  2. What is the ideal relationship between the CIO and the CEO?
  3. What are the core reasons buying processes take longer? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Yousuf Khan

Startup success is not exclusive to Silicon Valley. With more companies launching and thriving outside of Silicon Valley, regions such as ‘Silicon Slopes’ in Utah and ‘Silicon Alley’ in New York City are gaining traction within the startup scene. Podium, an interaction management platform for local businesses, was founded in Utah and grew from five employees in 2015 to more than 300 in 2019 to become one of the fastest-growing SaaS companies in the United States. In just four years, Podium has raised almost $100 million, with annual recurring revenue increasing to almost $60 million. Eric Rea, CEO of Podium, will share how he grew the company he launched from his spare bedroom into one of the fastest-growing SaaS companies in the country.

Bob Moore is the Founder & CEO @ Crossbeam, the startup that helps companies find overlapping prospects and customers while keeping the rest of their data private and secure. To date Bob has raised over $15m with Crossbeam from friends of the show including Andy @ Uncork, Matt @ Firstmark, Bill @ First Round and Matt @ Salesforce Ventures, to name a few. Prior to Crossbeam, Bob founded Stitched, a powerful ETL service built for developers that was acquired by Talend in 2018. Before that Bob co-founded RJ Metrics, where he built a global base of online retailers leading to their acquisition by Magento Commerce in 2016. 

In Today’s Episode We Discuss:

  • How Bob made his way into the world of SaaS and came to found Crossbeam?
  • As an entrepreneur, Bob has previously said, “no one is coming to save you”. What did he mean by this? What were the core mistakes that he made with RJ Metrics? Is it the responsibility of the board to course correct at this early stage? How does Bob determine whether to be visionary and determined vs realising when something is not working?
  • Does Bob agree with the notion that channel sales have completely died in the world of SaaS? Why is this? What are the drivers of it’s death? How important is it to own the entire customer journey? At what scale does that become impossible? In terms of replacement, what does Bob believe will be the emerging trends in SaaS Go To Market that will replace it? 
  • How does Bob think about when is the right time to hire a Head of Partnerships? In the early days, partnerships can be a distraction, how does Bob determine between right and wrong when determining whether to engage in a partnership? Where do most startups go wrong both in hiring for partnerships and in the engagements themselves? 

Bob’s 60 Second SaaStr:

  1. What is the hardest element of Bob’s role with Crossbeam today?
  2. What does Bob believe that most around him disbelieve?
  3. What does Bob know now that he wishes he had known at the beginning?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Bob Moore

The vision of exceeding sales, establishing credibility and successfully launching a product is no small task, especially when striving for that perfect introduction into the world of consumers. With so many articles, investors, and outside opinions, the true, simple tasks of launching can get lost in the noise. In this session, Jen Taylor, Head of Products at Cloudflare, will share her expertise and teach you to forget the noise, stick to the basics, and use 5 easy steps to turn that idea into a reality.

Tom Tunguz is General Partner @ Redpoint Ventures, the venture fund with a portfolio including the likes of Stripe, Netflix, Zuora, Hashicorp and Juniper Networks just to name a few. As for Tom, he joined Redpoint in 2008 and has since led investments in Kustomer, Looker, Expensify and Gremlin all prior guests on the show I hasten to add. He is also the co-author of Winning with Data: exploring the cultural changes big data brings to business. Tom has also been named on the Forbes Midas Brink list. Before joining Redpoint, Tomasz was the product manager for Google’s AdSense social-media products and AdSense internationalization.

In Today’s Episode We Discuss:

  • How Tom made his way from creating software with his father in Brazil to being GP and forefront figure in the SaaS investment community as a GP at Redpoint today?
  • Annual contracts: To what extent do annual contracts dominate today? How does this differ when comparing enterprise to SMB? Why does Tom think in the early days one should be wary of signing too many multi-year contracts? What are the dangers there? How does Tom think about calculating churn when it comes to multi-year contracts?
  • What were the findings on what good looks like when it comes to logo retention? How does this differ when comparing SMB to enterprise? What were the commonalities of leading indicators of churn? Is it fair to always surmise that when serving SMB one will always have a higher rate of churn? What is the right way to conduct a churn analysis?
  • Assisted vs unassisted: What does Tom believe are the leading benchmarks for both? How does this differ when comparing SMB to enterprise? How does the impact of a salesperson change the conversion rate? What time frame from SAL to closed lead suggests product market fit? What one question must all founders be asking in the sales process? 
  • How does Tom think about constructing comp plans the right way today? How should comp plans differ when comparing AEs to customer success? Where should the responsibility for upsell lie, customer success or sales? Should sales commission be paid on renewals?  

Tom’s 60 Second SaaStr:

  1. What does Tom know now that he wishes he had known at the beginning?
  2. What is Tom’s favourite book and why?
  3. What is Tom’s most recent investment and why did he say yes?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Tom Tunguz

 

The SaaS business model has risen to popularity for many reasons - it’s fast-paced, creates residual revenue streams, and well, the multiples are strong. However, while many are flocking to reap the benefits of the SaaS model, truly understanding how it works sustaining success over time is not as easy as some make it look. Rajesh is going to walk you through the key elements of winning the long game in SaaS - how to win customers, how to create long-term relationships, and how to avoid churn. He will also provide insights on the differences between commercial and enterprise customers and the key metrics to keep an eye on as you grow your business.

Congratulations you’ve built a product that’s proven itself in the marketplace! So how can you leverage that product’s success to obtain the valuation and funding you need to scale? Ashley Smith, Venture Partner at OpenView will provide insight on what investors are looking for in product metrics and growth indicators so you can capitalize on your product's story for funding.

Manny Medina is the Founder & CEO @ Outreach, the market leading sales engagement platform that turns your team into a revenue driving machine. To date, Manny has raised over $114m in funding from some great people including friends of the show in the form of Alex Clayton @ Spark, Mayfield, Trinity Ventures and DFJ Growth, just to name a few. Prior to founding Outreach, Manny spent 7 years with Microsoft where he ran the Latin America and Canada business development group for Microsoft’s emerging mobile division, representing $50M of yearly revenue. Befofe that Manny was a Senior Product Manager @ Amazon where he engineered the compensation system for Amazon Associates and Web-Services which accounts for 15% of Amazon's traffic. 

In Today’s Episode We Discuss:

  • How Manny made his way to found the leader in sales engagement from product management at Amazon and Business Development @ Microsoft?
  • How does Manny fundamentally approach managing top of funnel? What are the 2 big dangers of not managing it aggressively? What can be done to ensure not only full but high quality top of funnel? 
  • Why does Manny believe it is so important to track pipeline coverage as one of your core metrics? What does good look like when it comes to pipeline coverage? How does this change if you are creating vs in an existing market? How does Manny think about specialisation within the sales function? Why are SDR’s 99% of the time not able to carry leads to completion? 
  • How does Manny think about quota construction today? Does Manny err on the side of setting high to be ambitious or setting low to increase confidence? How can managers really empower their reps to be aggressive in hitting their quota and exceeding it? How does Manny think about resource allocation on the individual rep level? What is sufficient? What is excessive?
  • Does Manny believe that the founder should always be responsible for selling their product at one moment in time? How did Manny sell the first $1m in ARR simply through walking the streets of SOMA and selling door-to-door? What were his biggest lessons from doing this?  Why does Manny believe that you should not have a VP before $5m? 

60 Second SaaStr:

  1. What does Manny know now that he wishes he had known in the beginning?
  2. What does the future of sales prospecting look like to Manny?
  3. What would Manny like to change about the world of SaaS today?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Manny Medina

Lucidchart has been recognized as one of the most mature Product Lead Growth business models in the market, driving over 700,000 registrations per month, combined with a hyper-efficient B2B business model. It didn’t happen by accident. It happened through experimentation: from extensive A/B testing (with over 500 marketing tests completed in 2018), to testing crazy brand videos (which have garnered over 200 million views and was named the only ad campaign that truly mattered in 2018 by Adweek), to constant iteration and expansion of the business model.

Experimental marketing brings together the science and art of marketing, allowing for creativity that drives results. It’s an essential skill in the toolkit of the modern marketer, and one that’s easy to get started with, no matter your company scale.


Key Takeaways:

- Discover how to start or extend your marketing experimentation.
- Learn how marketing experimentation can apply across funnels, brands, and business models.
- Get tips on how to build a culture of experimentation that fosters creativity and drives business results.

Yousuf Khan is a serial CIO, start-up and VC advisor. Most recently Yousuf was the CIO & VP of Customer Success @ Moveworks, the advanced AI built for enterprise providing automatic resolution of IT issues. During his time at the company, they raised over $108m from Lightspeed, ICONIQ, Kleiner, Sapphire and Bain Capital. Pre Moveworks, Yousuf was CIO @ Pure Storage during their period of hypergrowth both as a private and public company. Finally, before Pure, Yousuf’s first role in the valley was with Qualys again as CIO where he owned the entire global IT budget.   

In Today’s Episode We Discuss:

  • How Yousuf made his way from the UK to the valley and how that led to his becoming one of the leading CIOs today in the rising prominence of CIOs in enterprise? 
  • How open and can transparent can CEOs be with CIOs? Do CIOs know the state of early-stage companies in terms of their cash situation, fundraising etc? Does that ever put them off buying? What is the right tone and temperament to take with those CIOs in the first meetings? How does Yousuf advise founders on quality or quantity of logos in the early days? 
  • How does Yousuf advise CEOs approach CIOs when it comes to discounting? Do they make a difference to the buying decision of the CIO really? Should founders offer discounts in exchange for customer testimonials? How can CEOs provide alternative forms of social validity to other CIOs in the ecosystem, other than case studies?  
  • How does Yousuf advise founders approach CIOs when it comes to multi-year deals? Does the mindset of the CIO change when the deal is paid upfront? How should the founders position that? When it comes to implementation, how important is time to value in the mind of the CIO? What is the worst thing a founder can do when discussing implementation?    

Yousuf’s 60 Second SaaStr:

  1. What separates good from great when it comes to CIOs?
  2. What makes the best board members?
  3. What are Yousuf’s biggest strengths and weaknesses?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Yousuf Khan

Salesloft CEO Kyle Porter, Zoom Head of Sales Ops Hilary Headlee and Fireeye VP of WW Sales Christina Foley share the seven tips and tricks to getting more revenue per AE.

Des Cahill is the Chief Marketing Officer for Oracle CX Cloud Suite, an integrated set of marketing, sales, commerce and service solutions that power customer experience for thousands of leading global brands. Prior to Oracle, Des was the CMO @ Kerio Technologies marketing to over 60,000 SMB customers and 5,000 channel partners. Before Kerio, Des was the CMO @ Ensighten, where he helped grow the customer base from 10 to 100 and revenues from $2M to $14M. Des has also spent time as CEO having founded and grown Habeas Inc from 0 to 450 customers, $9M in revenue and raising 3 rounds of venture financing. 

 In Today’s Episode We Discuss:

  • How Des made his way into the world of startups and came to be CMO of Oracle’s CX Cloud suite? 
  • Why does Des believe customers are more unpredictable now than ever before? How is their behaviour fundamentally changing? What are some great examples of how Des has seen companies amend to the changing consumer demands?
  • How does this change the role of the marketer today? How does this change the prioritisation of customer experience for marketers? What are the challenging elements of this change? How does the role of marketing also integrate with the post-sale and customer success with much of their content being used there?  
  • How does Des think about the relationship between marketing and sales teams? What are Des’ biggest tips on how to reduce friction in the handoff from marketing to sales? What works? What does not work? What is the right OKR to measure marketing teams? Does it have to be tied directly to revenue?  

Des’ 60 Second SaaStr:

  1. Biggest breakdown in the working of an efficient funnel?
  2. Who is killing it in SaaS marketing today and why?
  3. Advice in SaaS you commonly hear but disagree with?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Des Cahill

Kevin Egan, Slack's VP of North American Sales and Dannie Herzberg, Slack's Director of Sales as discuss their strategies for going from Freemium to Enterprise at Slack.

Allie Janoch is the Founder & CEO @ Mapistry, the startup that makes environmental compliance simple. As for Allie, prior to founding Mapistry she started her career in MIT’s Lincoln Lab before joining IQ Engines (acquired by Yahoo). Post acquisition, Allie integrated the technology built at IQ Engines into Flickr search. 

 In Today’s Episode We Discuss:

  • How Allie made her way from the world of Yahoo to founding the game changer of environmental compliance in Mapistry? Having had both big company, small startup and founding experience, what would Allie advise new graduates entering the workforce today? 
  • What were the biggest mistakes that Allie made when it comes to sales hiring? What were the learnings from those mistakes? How does Allie advise other founders on scaling sales teams? How does Allie think about sales rep payback period? How can one determine the effectiveness of a sales rep when they are engaging in 9-12 month sales cycles?
  • How does Allie think about the importance of focus applied to customer segmentation today? How does Allie measure true customer success? NPS? Churn? Product analytics? How does Allie explain the macro market size to VCs when they initially see the small customer segment?  
  • Why did Allie start doing their own events with Mapistry? How should startups think about whether events are the right strategy for them or not? How should founders think about resource allocation and budget when it comes to events? How does Allie measure the ROI of events? 

Allie’s 60 Second SaaStr:

  1. What does Allie know now that she wishes she had known at the beginning? 
  2. What would Allie most like to change about the world of tech and Silicon Valley?
  3. What is the biggest challenge for Allie today with Mapistry?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Allie Janoch

Hear about Adyen’s journey from a Dutch payments startup to a global public company with more than 15 offices around the world working with large global companies like Facebook, Spotify, Uber and Microsoft. Roelant shares lessons from the company’s own global growth path and will be giving practical tips for companies who are thinking about expanding their business globally. Roelant is joined by Felicis Ventures Founder, Aydin Senkut, who shares the commonalities he sees in successful companies...starting with culture.

Travis Bryant is Partner for Founder Experience @ Redpoint Ventures, the venture fund with a portfolio including the likes of Stripe, Netflix, Zuora, Hashicorp and Juniper Networks just to name a few. As for Travis, prior to joining Redpoint, Travis was head of Customer Growth at Front, after spending 5 years building the global Sales organization at Optimizely, the world’s most popular experimentation platform. During his time at Optimizely, the company grew from from $7 to >$90M in ARR and from 40 to 400 people. Before Optimizely, Travis spent 6 years at Salesforce in a number of sales roles including building the first Platform Sales team.

In Today’s Episode We Discuss:

  • How Travis made his way into the world of venture as the first ever Partner for founder experience at Redpoint? What were the 2 biggest lessons Travis took from Salesforce? How transformational is the 12 quarter year for Salesforce?
  • Why does Travis believe we need to abolish the title of CRO? Why does it suggest misalignment between customer and vendor from Day 1? What aspects of CRO’s roles is Travis in favour of? What elements is he not in favour of? What does Travis advise founders when it comes to uniting customer facing teams?   
  • Why does Travis believe that SaaS has upended the economic model but not the engagement model? How does the engagement model with customer need to shift? What does this do to the structure of the conventional funnel? 
  • Why does Travis believe net retention must always be the guiding North Star? How does Travis think about the different steps to customer qualification today and what makes the best SDR’s? What does Travis advise founders when it comes to churn analysis? What questions must you ask? What metrics must you look for? 

Travis’ 60 Second SaaStr:

  1. What motto or quote do Travis frequently revert back to?
  2. What is the most challenging element of Travis’ role with Redpoint?
  3. How should startup operators coming out of larger organisations determine which startup to join? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Travis Bryant

Nicole Alvino, founder of SocialChorus, shares some ‘truth is crazier than fiction stories’ about her time in structured finance at Enron and how she applied what she learned to build a company that has 10 of the Fortune 50 as customers. In your constant effort to grow and win, you’ll get the 5 most important lessons on how to push the envelope just far enough - while keeping your ethics in check.

Michael Pryor, Co-Founder & CEO @ Trello, now Head of Trello Product with Atlassian following their recent acquisition.

Kolton Andrus is the Founder & CEO @ Gremlin, the failure as a service startup finds weaknesses in your system before they cause problems.

Dylan Serota, Co-Founder and Chief Strategy Officer @ Terminal, the startup that helps you create world-class technical teams through remote operations as a service.

Rachel Carlson, Co-Founder and CEO @ Guild Education, the leader in education benefits offering the single most scalable solution for preparing the workforce of today for the jobs of tomorrow. 

Sid Sijbrandi, Founder & CEO @ Gitlab, a single application for the entire software development lifecycle.

Jeppe Rindom is the Founder & CEO @ Pleo, the simple spending solution for your company automating expense reports and simplifying company expenses.

In Today’s Episode We Discuss:

  • How should founders think about the debate between all remote vs part remote teams? How does life and operations change with each? What are the pros and cons? Is it possible to move between the two overtime?
  • What can one do to maintain culture with remote teams? What processes need to be in place to ensure a cohesive and streamlined communication process? What technical architecture needs to be in place? Where are the breakpoints when it comes to communication? How often does one need to do in person off-sites?
  • How does being remote or part remote impact fundraising? How do VCs think about this new structure of operations? What is the right way to present it? How does being outside a core tech hub impact one’s ability to raise? How should one run a fundraising process if outside a core hub?  
  • How important is it for your team to be near your customers? How does this change according to sector and customer base? How important is it for your team to be near your investors? Does having an exec and sales team in one place and the rest of the team elsewhere work?  

Jason Lemkin

Harry Stebbings

SaaStr

Rene Yang Stewart, Co-Head and Principal, Vista Equity Partners, and Monica Enand, Founder and CEO, Zapproved discuss growing a company from product market fit to scale. Vista Equity Partners invested in Zapproved in 2017. Hear perspectives from both the investor and founder on growth to scale.

How do you manage a sales team when you're a ta company with both Free and Freemium Sales-Driven Segments? What about SMB vs. Enterprise Sales? SaaStr CEO Jason Lemkin sits down with Mixmax's Head of Revenue Don Erwin to discuss it all.

Glassdoor CEO Robert Hohman and Battery Ventures' Neeraj Agrawal  walkthrough Glassdoor's $1.2 Billion story from its launch in 2008 to its 2018 acquisition by Recruit Holdings. Hear about the early days of Glassdoor; tactical lessons on scaling—from building a business model and recruiting an all-star management team to advice on building a compelling, innovative company culture; and learn whyGlassdoor’s $1.2 Billion acquisition is just one milestone in the early innings of the company’s story.

Krish Subramanian is the Founder & CEO @ Chargebee, the startup that lets you go beyond billing, payments and recurring invoices — to delivering subscription experiences that "wow". To date, Chargebee have “wowed” some of the world’s leading VCs to the tune of $38m including the likes of Insight Venture Partners, Tiger Global, Steadview and Accel Partners. As for Krish, under Krish’s leadership the team has grown to over 300 people and over 5,000 clients making it one of the next generation in truly global SaaS businesses started in India. 

In Today’s Episode We Discuss:

  • How Krish made his way into the world of SaaS and came to found one of India’s fastest growing SaaS companies in Chargebee?
  • What does Krish mean when he says, “in SaaS, you either sell to one of 2 customer profiles”? How does Krish think about purely serving the SMB market? Does one have to move to enterprise? Does one have to expand the product line to retain customers? How does he think about the mortality rate of SMBs?  
  • First, what is continuous customer development? Second, why does Krish believe it is one of the most important things any company must do? What is the process to do it efficiently? Does it have to be in person? What questions reveal the most? How should this data feedback into your product roadmap and pipeline? 
  • How does Krish think your customer acquisition and GTM strategy has to change with the movement from SMB to enterprise? What are the biggest challenges in making this transition? How does your customer success and customer support functions change with the move to enterprise? 

Krish’s 60 Second SaaStr:

  1. Biggest lessons from working with Lee Fixel?
  2. How does one know when is the right time to introduce a new product?
  3. What does Krish know now that he wishes he had known at the beginning?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings 

SaaStr

Krish Subramanian

When is the right time to go upmarket and how to you serve small, medium and large customers in the same company. SaaStr CEO Jason Lemkin sits down with Shopify Plus GM Loren Padelford to discuss.

Liat Bycel is VP of Customer Engagement @ Airtable, the startup that works like a spreadsheet but gives you the power to organise anything. To date, Airtable has raised over $170m in funding from some of the best in the business including Thrive, Coatue, Founder Collective, CRV and individuals like Patrick Collison, Ashton Kutcher and Raymond Tonsing to name a few. As for Liat, prior to Airtable, she was the Chief Revenue Officer @ Assist. Before Assist, Liat spent 6 years at Twitter where she first hand saw their hyper-growth, managing a team of 40 across New York and SF and also Liat achieved 102% to quota on average every year. Finally before Twitter, Liat was VP of Sales @ Revolution Prep where she led and managed 7 offices. 

 In Today’s Episode We Discuss:

  • How Liat made her way into the world of SaaS and came to be VP of Customer Engagement at one of Silicon Valley’s hottest startups in Airtable? 
  • What were Liat’s biggest lessons from Twitter on how to hire successfully? What were some of the key takeaways from that experience on how, why and when to fire? Is there ever a right way to do it? How does Liat think about aligning both the personal ambitions of the person with the wider objectives of the company? Why does Liat reject the notion of “hands off leadership?”  
  • Companies often worry about whether to go horizontal or vertical, how does Liat personally think about this choice? What does she advise founders as a result? What are the core questions they should ask to determine their strategy? What are the biggest challenges of having such a vertical product? How does it impact messaging and brand? Product roadmap? Pricing?
  • How does Liat think about challenging the traditional sales model? How does that challenge the structure of the conventional AE and SDR structure? How does Liat think Airtable is pushing up against the traditional customer success model? How has having children impacted how Liat thinks about operating today? What changes with children? 

Liat’s 60 Second SaaStr:

  1. What does Liat know now that he wishes he had known at the beginning of his time with Airtable?
  2. What are Liat’s biggest strengths and weaknesses?
  3. What are the challenges of prioritisation?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Liat Bycel

How do you manage a sales team when you're a ta company with both Free and Freemium Sales-Driven Segments? What about SMB vs. Enterprise Sales? SaaStr CEO Jason Lemkin sits down with Mixmax's Head of Revenue Don Erwin to discuss it all.  

Missed the session? Here’s what Jason and Don talk about:

  • How do you inject yourself as the revenue leader into the product building process?
  • How do you build a successful sales team?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Robert Vis is the Founder & CEO @ MessageBird, the company that allows you to talk to your customers via Voice, SMS and Whatsapp. The company raised a monster $60M Series A from Accel and Atomico with only one prior investor being Y Combinator. As for Robert, prior to MessageBird, he was co-founder and CEO of Zaypay.com which focused on driving mobile payments into 50+ countries, enabling 1.5bln users to pay for virtual goods through their phones (sold to Mobile Interactive Group (MIG). 

In Today’s Episode We Discuss:

  • How Robert made his way into the world of startups and SaaS and came to found Messagebird? What was the a-ha moment for him? 
  • Why does Robert believe the most important element of being a founder is “thinking big”? How as a founder do you balance between thinking big with investors and then the day to day in the weeds with the team? How does Robert as Europe’s mentality of thinking big today? Have our ambitions exceeded what they have been before? How does being in Benelux change how Robert thinks about global ambitions and growth ambitions?  
  • What does Robert mean when he tells founders, “don’t try to scale”? How does Robert think about knowing when a business is ready to scale? Where do many founders go wrong in the preparation for scale phase? What does one need to get in place before scaling?
  • Why did Robert wait 6 years before raising any VC money? Why did he decide then was the right time? Once the raise was in, did he feel the pressure of suddenly having a lot of VC funding? How did his mindset to capital allocation change post-raise? How did he see his decision-making process change post raise? How did raising from the US differ from raising in the UK? 

Robert’s 60 Second SaaStr:

  1. What does Robert know now that he wishes he had known at the beginning of his time with Messagebird?
  2. What keeps Robert up at night? 
  3. What are Robert’s strengths and weaknesses? 
  4. What advice in SaaS does Robert most often hear that he disagrees with?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Robert Vis 

David Cummings is the co-founder of the Atlanta Tech Village, Pardot which sold to ExactTarget/Salesforce.com, Hannon Hill,  Rigor, SalesLoft (raised over $75M in capital), Terminus (raised over $25M in capital), and several more. Hear his lessons learned over the years from Pardot to Calendly.

 

Missed the session? Here’s what David talks about:

  • How large a role does funding play?
  • Matching pricing to value
  • How to continuously level up talent

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Dave King is the Head of Marketing at Asana, the work management platform that teams use to stay focused on the goals that grow their business. To date, Asana has raised over $210m from some of the biggest names in tech including Mark Zuckerberg, Peter Thiel, Marc Andreesen, Ben Horowitz, Sean Parker, Ron Conway, Benchmark, Founders Fund and more incredible names. As for Dave, prior to joining Asana, he led the marketing teams at Percolate, Highfive, and Salesforce Community Cloud.

In Today’s Episode We Discuss:

  • How did Dave make his way into the world of SaaS and startups? When did he realise his love of marketing SaaS companies?
  • What does Dave mean when he says, “we are entering the 3rd wave of marketing”? What were the 1st and 2nd chapters? What does the “3rd wave” of marketing mean for marketers today? How does it change what marketing should be focusing on? How does it change how marketing works with sales and customer success? 
  • What does Dave mean when he says, “offsite’s serve as a crutch for 2 core elements of the marketer's role”? How does Dave advise marketers on crafting their playbook? What are the core questions to ask? Where does Dave see many going wrong here? How does one turn a playbook into a repeatable, measurable process? With channel volatility being so high, is it possible to have a repeatable and predictable process?  
  • What are Dave’s biggest observations on what B2B marketers can learn from B2C? How does that change how Dave thinks about new campaigns and community building with Asana today? Who does Dave think has done this particularly well in the world of enterprise? Are there any challenges to trying to carry over B2C into the world of B2B? 

Dave’s 60 Second SaaStr:

  1. What does Dave know now that he wishes he had known at the beginning of his career in marketing? 
  2. Biggest breakdown in the working of an efficient funnel?
  3. A moment in Dave’s life that has served as an inflection point and changed the way he thinks? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Dave King

Gillian oversees Talkdesk's Customer Success and Technical Support teams, partnering closely with customers to achieve their CX vision. In this session Gillian will walk you through how to build a high performing CSM Team.

 

Missed the session? Here’s what Gillian talks about:

  • How to build a CSM team
  • Avoiding the mistake of over defining the candidate profile
  • How to divide responsibilities across roles

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Jeppe Rindom is the Founder & CEO @ Pleo, the simple spending solution for your company automating expense reports and simplifying company expenses. To date, Jeppe has raised over $78m in funding for Pleo from some European favourites of mine in the form of Creandum and Vaestfonden and then also their most recent round led by Stripes Group in NYC. As for Jeppe, prior to founding Pleo he was the CEO @ Nodes, a design and development house that worked with brands including Loreal, BMW and Lego. Before that, Jeppe was the CFO @ Tradeshift where he first hand saw their scaling to 190 countries with offices in 6 different locations. 

In Today’s Episode We Discuss:

  • How did Jeppe make his way into the world of startups and SaaS with his becoming CFO @ Tradeshift? What were his biggest learnings from Tradeshift and how did that impact his operating mentality? What was that a-ha moment for him with Pleo?
  • Why did Jeppe decide to focus on SMBs from Day 1? How does the product build in the early days differ when building for SMB vs enterprise? Why does Jeppe believe that building for SMB makes it easier to build a great culture internally? How does Jeppe think about when is the right time to move into enterprise? What changes?
  • How does Jeppe respond to 3 common concerns VCs have with SMBs:
  1. The price points are so low that it takes huge volume to scale to meaningful revenue?
  2. The mortality rate of SMBs is so high that you are going to always have high churn due to the customer segment?
  3. Serving SMBs in the way that Pleo does is an intensely competitive space, is this a winner-take-all market? How does Jeppe think about competition? 
  • How does Jeppe think about NPS today? How does Jeppe approach the problem of agency when the buyer is not the user? How does Jeppe think about being customer informed but not customer-driven?
  • Pleo has a part-remote work structure, why does Jeppe advocate for this structure in the face of many saying it either has to be remote or not? What has Pleo done to make it work? What tool stack do they have to ensure seamless communication between remote and non-remote? Where are the challenges? What must one always do?
  • How does leadership change for Jesse in the face of scale? How does Jesse think about scaling humanity and the personal touch with the scaling of his leadership? What are the challenges? When do they start to arise? How has raising in the US compared to raising in Europe? What are the core differences? 

Jeppe’s 60 Second SaaStr:

  1. What does Jeppe know now that he wishes he had known at the beginning?
  2. How did raising from the US differ from raising with European investors?
  3. What would Jeppe most like to change about the world of SaaS today?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Jeppe Rindom

Gorgias helps brands automatically respond to basic questions, and track the impact of customer service on sales so support becomes a profit center. Join CEO Romain Lapeyre as he walks you through how to close your first 1000 customers based solely on data.

 

Missed the session? Here’s what Romain talks about:

  • How to build a growth machine
  • How you can tailor onboarding to customers
  • Using data to your advantage

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Ryan Bonnici is the CMO @ G2, the company that allows you to get the right software and services for your business with over 897,000 user reviews to help you make smarter buying decisions. As for Ryan, prior to G2 he was Senior Director of Global Marketing at Hubspot where among many other achievements, he scaled HubSpot's marketing-generated sales revenue by 330% year-over-year. Before Hubspot, Ryan was Head of Marketing @ Salesforce (APAC) where he led his team to achieve 227% YoY net-new sales sourced through marketing. Due to his success, Ryan has been named to Forbes’ List of World’s Most Influential CMOs.

In Today’s Episode We Discuss:

  • How Ryan made his way into the world of SaaS from Sydney, Australia and came to be one of the world’s leading CMOs with G2 today? What were Ryan’s biggest takeaways from his time at Salesforce? How did it change his mindset?
  • What are the core differences when comparing marketing functions at the likes of Salesforce to smaller companies like G2? What can they learn from each other? Where does Ryan sit on whether marketing is an art or a science today? How did Ryan turn a $6,000 initiative at Hubspot into a product that generated $64m net revs?
  • What have been Ryan’s biggest lessons in what it takes to acquire the best talent? How does Ryan build candidate pipe? What works most effectively? How does Ryan structure and run the process? What core questions does Ryan ask and find most revealing of the individual’s character? What does Ryan love to see in a candidate? 
  • Does Ryan agree that marketing teams should always be held directly accountable to a number tied to revenue? What type of CMO would Ryan bucket himself as; demand gen or brand? How does Ryan think about the relationship between the two? 

Ryan’s 60 Second SaaStr:

  1. What does Ryan know now that he wishes he had known at the beginning of his career in marketing? 
  2. What is the biggest BS that Ryan often hears in the world of marketing?
  3. Which marketing leader does Ryan most respect and admire and why?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Ryan Bonnici

SaaS is about creating long-term value for your customer, and being compensated appropriately for that value as a business. Learn actionable monetization tips from a Product/Growth operator turned VC.

 

Missed the session? Here’s what Naomi  talks about:

  • How to avoid underpricing your product
  • Fitting your businesses’ product to the market

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Max Yoder is the Founder & CEO @ Lessonly, the modern learning software used by teams to translate important work knowledge into Lessons that accelerate productivity. They have raised funding from the likes of former ExactTarget CMO Tim Kopp, OpenView Ventures and New York Times Bestseller Jay Baer just to name a few of the impressive figures involved. Fun tact; they are based in Indianapolis and so Max brings a fantastic perspective on scaling and operating a growing SaaS business outside Silicon Valley.

In Today’s Episode You Will Learn:

  • How Max made his way into the world of startups and came to found Lessonly, one of the hottest SaaS startups outside of Silicon Valley?
  • Max has previously stated that ‘SaaS scaling happens in 3 stages’. What are those stages? What is the most challenging stage? How does the CEO need to transition with each stage?
  • How does Max view the scaling of the team? Why does Max think it is bad to give large and often inflated titles in the early days? How can CEOs most effectively look to place people in the right place to ensure the most productive of scaling?
  • What does Max most look for in potential Lessonly employees? Why is it so fundamental that candidates have experienced some form of professional hardship before?
  • How does Max view the role of the board in the scaling of a SaaS organisation? What are the components that make the best boards? What are the components that make the best board members?

60 Second SaaStr

  1. What one hire does Max wish he had made sooner?
  2. What SaaS reading material can Max not live without?
  3. Pros and Cons of running a SaaS startup outside the valley?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Max Yoder

Stacey Epstein is the CEO @ Zinc, the secure communications platform for workers in front of customers, not computers. They have backing from some of the best in SaaS investing including the likes of Jason Green @ Emergence, CRV with George Zachary and GE Ventures. Prior to Zinc, Stacey was CMO at Banjo. Before Banjo, Stacey was CMO at ServiceMax where she helped fuel 5 consecutive years of triple-digit growth. Finally, before ServiceMax, Stacey was the Vice President of Global Marketing Communications at SuccessFactors. During her tenure with SuccessFactors, Stacey pioneered the marketing function in 2005, and was instrumental in the company’s successful IPO in 2007, which led to a $3.4B acquisition by SAP in 2010.

In Today’s Episode You Will Learn:

  • How Stacey made her way from Executive Assistant working for another Executive Assistant before moving to CMO and today as CEO?
  • What were the fundamental lessons Stacey took from her career as CMO to now being CEO/ What were some of the hardest elements of the transition?
  • What role should the CEO play in the marketing strategy and execution? What do CEO’s most often get wrong about CMO’s?What is the optimal and most efficient working relationship between CEO and CMO?
  • How does Stacey create alignment and strong and successful communication between the traditionally conflicting sales and marketing? How does transparency help drive better business results?
  • How can one look to instill these values and communication standards on inherited organisations they they did not found? Are there any drawbacks to transparency and communication?

60 Second SaaStr

  1. What hires does Stacey wish she had made earlier?
  2. What can females do to master the art of negotiating?
  3. Recruiting in the valley today, how tough and top tips?
  4. When is the right time to hire your CMO?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Stacey Epstein

Auren Hoffman is the Founder & CEO @ Safegraph, the startup that is unlocking the world’s most powerful data so that machines and humans can answer society's toughest questions. They have backing from likes of Naval Ravikant and prior guests of the show including SignalFire, IDG Ventures and David Rodnitzky just to name a few. Prior to Safegraph, Auren has an astonishing 5 successful exits under his belt with one being, LiveRamp (sold to Acxiom for $310m in 2014). If that was not enough, Auren is also a prolific angel investor with a portfolio including the likes of ThumbTack, Rainforest QA, Brightroll and Groupon.

In Today’s Episode You Will Learn:

  • How Auren made his way into the world of SaaS and came to found his 6th SaaS startup in Safegraph?
  • Auren has said before there are two types of successful sales people, what are these two types and what are their character profiles? What type of company should have each different profile? How does each profile interact differently with the rest of the company?
  • Why does Auren take the contrarian view and saying that highering your price is not always the right answer? In what markets is it right to higher or lower your price? When is it the wrong time? What percentage of revenue should sales and marketing be at a healthy SaaS startup?
  • Why does Auren believe that you can actually grow faster by having fewer employees? In what situation and start does this work and when does it not? ?
  • Why does Auren believe that the CEO should never delegate HR? What does Auren mean when he says the best HR professionals are real capital allocators?

60 Second SaaStr

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Auren Hoffman

Promise Phelon is the CEO @ TapInfluence, bringing the first ever influencer marketing platform to the Fortune 1000. Under Promise’s leadership the company has enjoyed a 300% increase in revenue in 2015 alone, they made the successful transition from a services to a SaaS model and were successful in raising a fantastic $14m Series B. Prior to TapInfluence, Promise was the Founder and CEO at 2 startups, one of which, The Phelon Group, grew to 8 figure revenues and was successfully acquired in 2009. Before that, Promise got her start at BEA systems.

In Today’s Episode You Will Learn:

  • How Promise made her way into the world of SaaS and came to be at BEA systems, one of the most exciting companies in the valley at the time?
  • How does Promise view the importance of building long lasting relationships with colleagues? How does Promise suggest is the right way to leave a job and sustain the best communication and relationship with former employers and colleagues?
  • What does Promise mean when she states the importance of upward empathy? What are the benefits of installing this in your organisation? What is the right way to breed a culture of upward empathy?
  • How does Promise differentiate between ‘advocate’ and ‘mentor’? What is the right way to attain each of these? At what point in one’s career is the right time to have each of these?
  • What does Promise believe is the formula for making the successful transition from a services based business to a SaaS business? How can one make the change without significant customer churn and revenue loss?

60 Second SaaStr

  1. What does Promise know now that she wishes she had known at the beginning?
  2. How does motivating people differ when outside of the valley?
  3. Should customer success be able to upsell?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Promise Phelon

Ashu Garg is a General Partner @ Foundation Capital whose portfolio includes the likes of Uber, Lending Club, Adroll and Netflix, just to name a few. As for Ashu, at Foundation he has led investments and naming just a few of them here, in the likes of Conviva, Localytics and TubeMogul, later going public in 2014. Prior to Foundation, Ashu was the General Manager for Microsoft’s online advertising business.

In Today’s Episode You Will Learn:

  • How Ashu made his way from completing to the Rubik's cube as a kid in 25 seconds to being a leading SaaS VC?
  • How does Ashu really define scaling a SaaS company? What does product market fit really look like with regards to ARR growth?
  • What are the 3 fundamentals that SaaS founders have to nail if they are to scale to $30m+ ARR? Why does Ashu believe it is so important to have a single insertion point? What does this mean for SaaS founders?
  • What does Ashu advise first time founders making their first foray into the world of SaaS? How should they think about obtaining and building an ecosystem of mentors? How should they manage weaknesses within their own skill sets? Does Ashu believe with Aaron Levie @ Box, “anyone can learn to be a great CEO”?
  • Where do technical founders most often struggle? What can be done to help them go from 0-1 on customer acquisition? Where do business led founders most often struggle? How must they think of the engineering element as a core part of the founding team?

60 Second SaaStr

  1. What does Ashu know now that he wishes he had known at the beginning?
  2. Chats: Fad in the enterprise or here to stay?
  3. Biggest inflection points and breaking points in SaaS company growth?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Ashu Garg

Kurt Bilafer is the CRO @ WePay, the most complete payments solution for platforms. To date, they have raised close to $75m in VC funding from some of the best in the business including Max Levchin and August Capital just to name a few. As for Kurt himself, prior to WePay he has had experience both in startups and large corporations with his founding of Pilot Software, sold to SAP in 2007, where he spent a further 7 years holding titles such as a Global Vice President of Sales and Director of Strategic Accounts.

In Today’s Episode You Will Learn:

  • How did Kurt make his way into the world of SaaS? What were Kurt’s big takeaways from seeing the internal machinations of SAP?
  • What is the one metric that guides Kurt’s thinking? How can you calculate your “magic number” for your business? Why must SaaS founders switch from activity based metrics to KPI’s?
  • How does Kurt assess scalability and repeatability of revenues? What is a reasonable ratio for sales and marketing expense to revenue?
  • Why should SaaS founders focus on the LPI of “time to money”. How can they look to optimize this? How has Kurt seen the enterprise sales cycles change since his time with SAP?
  • How does Kurt assess conflict within the sales and marketing teams and customer success and product teams? How can managers look to implement an element of prioritization into what sales teams submit to product teams?

60 Second SaaStr

  1. What does Kurt know now that he wishes he had known at the beginning?
  2. What is the worst piece of SaaS advice that Kurt commonly hears being given out?
  3. What should one look for in their VP of Sales?
  4. What mistake does Kurt see most in the world of SaaS?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Kurt Bilafer

Jens Nylander is the Founder and CEO @ Automile, the startup that makes fleet and asset management much much easier. They have backing from some of the best in the business including Godfather of SaaS himself Jason Lemkin, the wonderful team at Point Nine, Justin Kan and Dawn Capital in London. As for Jens, he really is a serial entrepreneur with past endeavours including creating Sweden’s largest music player and founding Jays, the manufacturer and developer of innovative headphones that went public and is listed on the NASDAQ.

In Today’s Episode You Will Learn:

  • How did Jens make his way into the world of SaaS and come to found Automile?
  • How does Jens look to build a repeatable scalable sales process with Automile? What are the core infrastructure requirements needed to make the process as automated as possible?
  • How does Jens evaluate selling into the SMB market? How does Jens look to optimise the onboarding process to maximise conversion? How does Jens look to minimise churn with a market as potentially unstable as SMB’s?
  • Why does Jens prefer technology minded sales teams? What benefits do they bring in terms of process to the sales cycle? What should founders look for in potential new engineering led sales teams?  
  • Jens is increasing transparent, posting numerous figures on Twitter, what are the benefits of such transparency? How does that help the team to achieve the wider goal? Are there any cases, such as fundraising or exits, where transparency has negative consequences?

60 Second SaaStr

  • What was the hardest element of leaving Europe to go big in the US?
  • What does Jens know now that he wishes he had known at the beginning?
  • What hires does Jens wish he had made earlier?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Jens Nylander

Steve Loughlin is a Partner @ Accel in San Francisco, one of the leading funds with prior investments in the likes of Facebook, Dropbox, Atlassian, Slack and many more incredible companies. Prior to Accel, Steve was the CEO and co-founder of RelateIQ, later named SalesforceIQ following the acquisition of the company by Salesforce in 2014 for $390 million. Steve was also president and CEO of Affinity Circles, a professional social network that connected more than 18 million professionals. Steve has also advised or invested in the likes of Palantir Technologies, Addepar, and Roam Analytics.

In Today’s Episode You Will Learn:

  • How Steve made his way into the world of SaaS with the founding of RelateIQ and then came to be a Partner at Accel on the other side of the table?
  • Why does Steve believe the hardest balance a founder has to consider is the balance between building for the future and building for the present? How can this short to long term dichotomy be considered effectively by the team?
  • RelateIQ was early to the AI/ML landscape, what does Steve think they did so right with RelateIQ? Does Steve agree that for an enterprise ML play to be interesting it must fundamentally change the go to market strategy?
  • What were the key learnings from working so closely with Marc Benioff on the Salesforce exec team? What is it about the internal structure and operations of Salesforce that make it the massively profitable behemoth that it is today?  

  • Having been a founder himself and now a VC, how does Steve look to help founders specifically? Where has Steve found that early stage founders need the most help? Where do VCs proclaim to help the most but really do not at all? 

60 Second SaaStr

  1. What is the worst advice Steve often hears being given?
  2. What is something that Steve has changed his mind radically on over the last few years?
  3. What is Steve’s favourite SaaS reading material?
  4. What does Steve know now that he wishes he had known at the beginning?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Steve Loughlin

May Habib is the Founder & CEO @ Qordoba, the best platform for building truly localized products across apps, websites and marketing content. It is the fastest, most scalable way to grow from one market to many. We do also want to say a big congratulations to May for recently raising a fantastic Series with the likes of Upfront Ventures and Rincon Partners leading the round. Prior to founding Qordoba, May was Director of M&A at Mubadala and an investment banker at Lehmann Brothers and Barclays in New York. May has also been named to the 30 Under 30 and CEO of the Year award.

In Today’s Episode You Will Learn:

  • How May made her way from North Lebanon to founding one of the hottest early stage SaaS companies on the West Coast?
  • May has quadrupled her MRR growth since last year through ‘turning her SDR’s into the smartest people in the space’. What does this mean? How can this be done and replicated? What “SDR best practices did May follow that damaged her?
  • May has a unique approach to scaling prospect search, how does this play out Does May agree with Mark Suster with regards to always calling high on customer outbound? Why does May think there is only value in outbound to seriously qualified leads?
  • Why does May believe that startups are wrong to think that they have to start at SMB and then move up to enterprise? How can startups immediately start with enterprise? What advice does May have in terms of asking for those big ACV’s as a small startup?

  • What advice did May receive during her fundraising that she found particularly jarring? What other than funds does May believe fundraising can be particularly good for? 

60 Second SaaStr

  1. What does May know now that she wishes she had known at the beginning?
  2. What is May’s favourite SaaS reading material?
  3. Hardest moment in the journey with Qordoba?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

May Habib

Nicolas Dessaigne is the Founder & CEO @ Algolia, the most reliable platform for building search into your business. Just last week they raised $53m in funding led by Accel with participation from Jason Lemkin @ SaaStr, Point Nine Capital, AppDynamic’s Jyoti Bansal, Intercom’s Des Traynor and InVision’s Clark Valberg and more incredible investors.

In Today’s Episode You Will Learn:

  • How Nicolas made his way to YC and came to found Algolia?
  • What are the key things that change when you cross the 10m in ARR milestone? What have been the fundamental learnings in the march to $10m in ARR?
  • Jason Lemkin has said before that ‘the first 10 unaffiliated customers you get is the first sign of pre-success’. Does Nicolas agree with him here? When are the first signs of pre-success for Nicolas?
  • Does Nicolas agree with Jason that $1m-$2m in ARR is always the hardest for a scaling SaaS startup? Which element did Nicolas find most challenging? How has Nicolas seen himself change and develop as a leader with these inflection points?

  • What are the fundamental to building a successful developer community? What have Algolia done to do this so successfully? What mistakes do other startups normally make in their pursuit of this? 

60 Second SaaStr

  1. What hires does Nicolas wish he had made earlier?
  2. What does success look like for Nicolas with Algolia?
  3. What does Nicolas know now that he wishes he had known at the beginning?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Nicolas Dessaigne

Ryan Carson is the Founder & CEO @ Treehouse the startup that teaches you to code and learn the skills needed to launch a new career. They have backing from some of the best investors in the business including the likes of Social Capital, Greylock Partners and then notable individuals such as Reid Hoffman, Josh Elman and Mark Suster just to name a few. As for Ryan, prior to Treehouse he was the creator of famous The Future of Web Apps Conference, showing his unparalleled access to the top tier of West Coast founders. Due to the success of the conference, Ryan later sold the event to another events company.

In Today’s Episode You Will Learn:

  • How Ryan made his way into the world of startups and came to found Treehouse?
  • How does Ryan think all founders can build a truly diversified pipeline for developer talent? How does Ryan detect the seeds of potential in young engineers? How does he nurture them to grow and fit the desired role?
  • How does Ryan approach regrettable and non-regrettable churn? What is the dunning process? Why is it so important to instantly increase retention and reduce churn?
  • Does Ryan agree with Jason Lemkin that the hardest element of SaaS scaling is the $1-2m phase? Does Ryan agree with Jason in suggesting that your first 10 unaffiliated customers is the first sign of product market fit?
  • Ryan has previously said, ‘as a founder, there is one thing you need, otherwise you will quit’. What is the one thing? Why is it so important?

60 Second SaaStr

  1. Why does Ryan know now that he wishes he had known when he started?
  2. What is Ryan’s favourite SaaS reading material?
  3. Freemium in SaaS: What are the pros and cons?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Ryan Carson

Jeetu Patel is Senior Vice President of Platform and Chief Strategy Officer of Box where he leads the Box Platform organization, driving the strategy of the platform business and developer relations. He also oversees the corporate strategy and development organization for Box. Before joining the company, Patel was General Manager and Chief Executive of EMC's Syncplicity business unit. Prior to EMC, Patel was president of Doculabs, a research and advisory firm focused on collaboration and content management across a range of industries.

In Today’s Episode You Will Learn:

  • How Jeetu made his way into the world of SaaS and came to be one of the key executives at Box?
  • What are Jeetu’s 3 tips to startup founders looking to build high performing teams? Why does Jeetu believe that team sizes must always remain small? What are the inflection points in team size when dynamics change?
  • What does Jeetu argue that founders must pursue really hard problems? What are the benefits of this when hiring new people to the team? How does Jeetu balance between visionary hard problems and unrealistic?
  • What does Jeetu mean when he says, ‘do things that do not scale so you can do things that sustainably scale? What are some examples of how this has been done effectively? Where do most startups go wrong in scaling sustainably?

60 Second SaaStr

  1. What does Jeetu believe that most around him do not?
  2. Fave SaaS reading material?
  3. Why businesses will find the rules of the future very different to the rules of the past?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Jeetu Patel

Laura Bilazarian is the Founder & CEO @ Teamable, the startup that allows you to recruit the best talent from your network. They have raised funding from some stellar investors including the likes of True Ventures and SaaStr. As for Laura, she started out her career on Wall St before making forays into the world of Vietnamese hotel building and being a National Rugby Champion. Laura has also spent time with the likes of Fairmount Partners where she worked on dozens of M&A transactions to large public companies.

In Today’s Episode You Will Learn:

  • How did Laura make her way from Wall St to rugby captain to founder of SaaS startup, Teamable?
  • Why does Laura believe that “you should always be premium”? What are the benefits to this? How does this affect how Laura views both freemium versions of products and free trials?
  • Why does Laura believe that you have to “create an outbound sales culture as early as possible”? Why is this? Does this change according to the differing customer profiles?
  • How can SaaS businesses aid in the closing of their clients? What can they do to make this process as seamless and easy as possible? What are the requirements for this process?
  • Why does Laura believe there are only ‘2 ways to hire’? What are those 2 ways? What methods of inbound applications must be ignored? How can founders ensure continued quality when hiring at scale?

60 Second SaaStr

  1. What does Laura know now that she wishes she had known at the beginning?
  2. What is Laura’s fave SaaS reading materials?
  3. Competitive advantages of being a female CEO?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Laura Bilazarian

Mark Suster is Managing Partner at Upfront Ventures which he joined in 2007, having previously worked with Upfront for nearly 8 years as a two-time entrepreneur. Before joining Upfront Mark was Vice President, Product Management at Salesforce.com following its acquisition of Koral, where Mark was Founder and CEO. Prior to Koral, Mark was Founder and CEO of BuildOnline, a European SaaS company that was acquired by SWORD Group. Mark is also the writer of one of my favourite VC blogs, Both Sides Of The Table which is a centre piece to the whole VC community and is a must read for all interested in entrepreneurship and VC.

In Today’s Episode You Will Learn:

  • How Mark made his way into the world of startups and came to invest in SaaS with Upfront today?
  • What are 4 reasons why startups should prioritise professional services in the early days? Why do most VCs disagree with this? How did Salesforce do this right in their period of hyper-growth?
  • How should early stage startups approach the topic of pricing? How can they evaluate whether to call high or low? What are the pros and cons of doing both?
  • Mark has previously discussed the importance of finding your champion in the buying process. How can startups determine whether your champion is a decision-maker? What questions can you ask to find this out?
  • What changes as a SaaS business scales? What are the key inflection points of company development? How does Mark view the amount B2B startups are raising today? How does Mark evaluate responsible and right spend?

60 Second SaaStr

  1. What should your first sales reps be really good at?
  2. How has Mark seen early stage SaaS startups go wrong most often?
  3. IPO markets, frothy or fantastic?
  4. What does Mark know now that he wishes he had known before?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Mark Suster

Today’s show is centred around The Top 10 VP of Sales Lessons Learned In Scaling To $100M ARR. Leading this conversation is Aaron Ross, author of best selling book, Predictable Revenue, providing the framework for the outbound process & sales team Aaron created for Salesforce.com. During his time at Salesforce as Director of Corporate Development and Acquisitions, Aaron added an extra $100 million in revenue in just a few years. Joining Aaron from the sales perspective we have Andrew Bothwell, VP of Sales @ TalkDesk and Aaron Schilke, VP Enterprise Sales @ Talkdesk, one of the fastest growing SaaS startups today. Providing insight from the other side of the table we have Josh Stein, Partner @ DFJ where his current board responsibilities include Box (NYSE: BOX), Chartbeat, LaunchDarkly, LendKey, SugarCRM, and previous guest with me on SaaStr in Talkdesk. But enough from me so without further ado I am going to hand over the reigns to Aaron Ross.

In Today’s Episode You Will Learn:

  • What does Josh Stein believe is the toughest growth stage in SaaS? Which stage separates the men from the boys?
  • Why is growing to 100 a case of simple maths? How does this maths affect how you should think about your sales hiring pipeline? How does this maths affect your view of forecasting?
  • How do TalkDesk look to build a repeatable and scalable sales process? What have been their major learnings? Where do most startups make mistakes and falter?
  • How should VPs of sales approach feedback with their reps? Why has a VP failed if a rep is blindsided by a particular piece of feedback?

 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Edith Harbaugh is the Founder & CEO @ LaunchDarkly, the startup that allows you to fearlessly and swiftly release software by separating feature rollout from code deployment. They have raised over $10m in funding from many previous guests of The Twenty Minute VC including Andy McLoughlin @ SoftTech, Josh Stein @ DFJ and the wonderful team at Bloomberg Beta. As for Edith, prior to LaunchDarkly, she was a Director of Product @ Tripit and Concur. Edith also holds two patents in deployment from her time in engineering at Vignette.

In Today’s Episode You Will Learn:

  • How Edith made her way into the world of SaaS and came to found LaunchDarkly?
  • Does Edith agree with Jason Lemkin that the hardest element is the 1-10 customer phase? How has Edith navigated this process with her differing companies?
  • How does Edith look to structure her sales team to successfully close Fortune 500 deals? What is the fundamental difference in selling to enterprise rather than SMB?
  • What can founders do to make NPS a more intelligent metric? How can NPS be analysed effectively to tell you more about the state of your business?
  • What are the signs of a truly great sales person? How do they aid not only their company but the customer they are serving? What is their required knowledge base?

60 Second SaaStr

  1. What is Edith’s fave SaaS resource?
  2. What does Edith know now that she wishes she had known before?
  3. Oakland Office: Why not SF? What are the benefits?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Edith Harbaugh

 

Lauren Vacarrello is VP of Marketing @ Box, one of the leading enterprise B2B brands today. At Box, Lauren leads a 50 person team that involves demand generation, global campaigns, events and more. Prior to Box, Lauren was VP of Marketing @ Adroll, where she built and scaled a 25 person global marketing team from the ground up. If that was not enough, Lauren is also the Co-Author of “The Retargeting Playbook” and “Complete B2B Online Marketing”.   

In Today’s Episode You Will Learn:

  • How does Lauren view the relationship between sales and marketing? Why does Lauren believe the ARR pipeline is not just the responsibility of the sales team?
  • Why is lead nurturing not just about email? What are the other core components to ensure successful progression of leads through the funnel?
  • How does Lauren view successful lead segmentation? Why does Lauren like to segment leads into 3 distinct buckets? How does this strategy play out at different ends of the market?
  • What is the role of marketing post-purchase? How has Lauren seen this change since the early days of her career? How does this differ when comparing SMB to enterprise?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Lauren Vaccarello




Aaref Hilaly is a Partner @ Sequoia Capital, one of the world’s most successful VC funds with investments in the likes of Apple, Google, Paypal, Whatsapp and LinkedIn just to name a few. As for Aaref he came to the valley with 2 suitcases and the ambition to start a company. That he did and had 2 companies that were Sequoia backed, first CenterRun and then ClearWell Systems where Aaref was instrumental in the company’s growth from 0 to a $100m revenue run rate in just 4 years, prior to their $410m acquisition by Symantec. Today Aaref draws on this incredible operational success to illustrate how to manage up and have a very happy board.

In Today’s Episode You Will Learn:

  • Why does Aaref advocate for founders not to manage the board but to engage them? How can this be done effectively?
  • What does Aaref state are the dangers of focussing on metrics with your board? Why should you focus on product instead? How does this shift change the dialogue with the board?
  • When things do go wrong and the company misses a quarter, how should the founder react? Why does Aaref suggest that founders need to own the miss? How should they structure these conversations? What should they not do when they miss a quarter?
  • How can founders most effectively put their board to work? How should this be communicated and then followed up on by the founder? Where has Aaref found the board can provide the most value?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Aaref Hilaly

Mark Roberge is a Senior Lecturer @ Harvard Business School where he teaches entrepreneurial sales and marketing. Prior to his role with HBS, Mark was the Chief Revenue Officer @ Hubspot where he increased revenue over 6,000% and expanded the team from 1 to 450 employees. As a result, Mark has been named Forbes' Top 30 Social Sellers in the World and awarded the 2010 Salesperson of the Year by MIT.

Michele Law is an investor and advisor specialising in building and executing on go to market strategies, creating new revenue models and the operations to support them. Michelle has sat on both sides of the table having been a Principal at Greylock for 8 years before moving to be COO at OpenDNS where she led the sales and customer success team growing enterprise revenue from $0 to $20M ARR in 4 years, prior to the company’s acquisition by Cisco for $635m. Michele then moved to Castlight Health where she grew revenue from $13 to $75m.

In Today’s Episode You Will Learn:

  • Why it is fundamentally dangerous to prematurely focus on growth? How can founders know when is the right time to focus on growth? What does the path to growth phase look like?
  • How should founders assess and structure the core components: customer success, unit economics and growth? In which order should they be prioritised? What does the funnel look like?
  • What should the profile of your first sales hire be? How can founders understand who and when to hire? From Hubspot days, when has Mark seen the transition from generalist to specialist?
  • What should your sales compensation plan look like in the early days of the company? Why does Mark believe that churn is rooted in the sales compensation plan?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

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Todd Olson is the Founder & CEO @ Pendo, the startup that allows you to capture all user behaviour, gather feedback and then provide contextual support.  They have raised over $30m in VC funding from some of the very best in the business including Neeraj @ Battery Ventures, Megan @ Spark and Matt @ Salesforce Ventures just to name a few. As for Todd, prior to Pendo he held various different roles in product as well as co-founding 2 prior startups.

In Today’s Episode You Will Learn:

  • How did Todd make his way into the world of SaaS and come to found Pendo?
  • Why does Todd believe that there is inherent tension between customer success and product teams? How has this changed from sales and marketing team tension? What does Todd suggest to mitigate this tension?
  • How does Todd evaluate his hiring process? At what stage does one become a specialist vs a jack of all trades? Why does Todd always believe that you should hire ahead of where you are?
  • Todd has previously said that ‘money is not all the same’. How does Todd look to select his investors? What value adds are most desired for Todd? What do the best investors do that make them so?

60 Second SaaStr

  1. What does Todd know now that he wishes he had known in the beginning?
  2. What is Todd’s favourite SaaS reading material: Mattermark Daily, Tom Tunguz
  3. Creating a startup culture for adults?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

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Todd Olson

Amit Agarwal is the Chief Product Officer @ Datadog, the startup that provides cloud scale monitoring that tracks your dynamic infrastructure and applications. They have raised over $140m in VC funding from some of the best in the business including Index Ventures, IA Ventures, OpenView and RRE just to name a few. As for Amit, before Datadog, Amit was the Director of Product Management at Quest Software (now Dell), where he led the team responsible for application performance monitoring. Previously, Amit held product management roles at Datamirror (now IBM) and Embarcadero Technologies.

In Today’s Episode You Will Learn:

  • How did Amit make his way into the world of SaaS and come to be Chief Product Officer @ Datadog?
  • Why did Datadog not have a marketing strategy for the early days? What would Amit advise early stage founders with regards to optimising their marketing in the early days?
  • Obviously a multi-product line is crucial for a SaaS startup to be successful, what is Amit’s take on how, when and why to launch a second product? What have been his big learnings on this from Datadog?
  • Amit has said before that it is tough to sell to large enterprises in the early days, does that mean startups should always start with SME’s? At what price point does it become a challenge? Does Amit agree that if you are between 25K-100K you are in the valley of death price wise?

60 Second SaaStr

  1. What does Amit know now that he wishes he had known in the beginning?
  2. What is Amit’s favourite SaaS reading material?
  3. When is the right time to hire a CPO and why?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

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Amit Agarwal

Tim Eades is the CEO @ at vArmour, the industry's first distributed security system that provides application-aware micro-segmentation. Tim joined vArmour as CEO in October, 2013. Prior to that, he was the CEO at Silver Tail Systems until the company was acquired by RSA, the security division of EMC in late 2012. Prior to leading Silver Tail Systems, Tim was CEO of Everyone.net, an SMB focused SaaS company that was acquired by Proofpoint. Tim has also held sales and marketing executive leadership positions at BEA Systems, Sana Security, Phoenix Technologies and IBM.

In Today’s Episode You Will Learn:

  • How did Tim make his way from punk rock fan in the UK to leading Silicon Valley CEO?
  • Why does Tim believe Incremental Account Opportunity (IAO) is one of the most important metrics for a growing startup?
  • Why does Tim believe that most founders are far too late to ship their second product? How can they identify adjacent markets? When exactly is the right time to know when to ship your second product?
  • What does it take in terms of sales team structure to successfully orchestrate the 7 figure deals that Tim does? What does that look like in terms of sales team compensation?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Tim Eades

David Rodnitzky is founder and CEO of 3Q Digital, a leading digital agency that was acquired by Harte Hanks in 2015. Prior to 3Q Digital, he held senior marketing roles at several Internet companies, including Rentals.com (2000-2001), FindLaw (2001-2004), Adteractive (2004-2006), and Mercantila (2007-2008). David currently serves on advisory boards for several companies, including Marin Software, MediaBoost, Mediacause, and a stealth travel start-up.

Loretta Jones is the vice president of marketing at Delighted, the fastest way to gather customer feedback and put it into the hands of those who can act on it.  Prior to Delighted, Loretta's marketing programs grew Insightly, a CRM for small business, from 100,000 users to over 1.2 million users. Prior to Insightly, Loretta worked at Adobe Sign (formerly Adobe EchoSign) and grew the EchoSign brand to $25 million.

In Today’s Episode You Will Learn:

  • Should all companies invest in SEM?
  • How does SEM differ for SaaS SMB businesses vs enterprise SaaS businesses?
  • How much of a role should iterating and testing play with regards to SEM? What are the strategies that can be used to ensure for maximal dollar efficiency?
  • David has said before that ‘no demand channel is an island’. How does SEM work together with the other channels (SEO, display ads etc) to form a cohesive marketing strategy?
  • As LTV takes a considerable time to figure out and can be inaccurate, should startups focus on their CPA (cost per acquisition) more than any other metric?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

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David Rodnitzsky

Tom Tunguz is a Partner at Redpoint Ventures and one of the pre-eminent thought leaders in the rise of SaaS. Tom has made investments in the likes of Demio, Axial, Chorus.ai and more incredible companies. Tomasz is also the co-author of Winning with Data: which explores the cultural changes big data brings to business, and shows you how to adapt your organization to leverage data to maximum effect. Before joining Redpoint, Tomasz was the product manager for Google’s AdSense social-media products and AdSense internationalization. If you have not checked out Tom’s blog that is a must and can be found here.

In Today’s Episode You Will Learn:

  • What are the 4 dominant ways startups are incorporating machine learning into their feature set? Why does Tom not believe in AI and discuss prefers to discuss machine learning?
  • What 3 things have caused the rise of machine learning? Why now will machine learning happen in core categories in SaaS? What role does deep learning play in this rise?
  • What are the 5 precepts of the type of companies that Tom wants to invest in using ML in SaaS? Why should startups discuss their value proposition over their technology?
  • How does Tom advise startups can gain access to proprietary datasets? How would Tom like to see data access change in the coming years?
  • How does Tom approach the aspect of building out a team of experts in machine learning for your startup? What should founders look for?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

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Tomasz Tunguz

Dan Adika is the Founder and CEO @ Walkme, the cloud-based service designed to help professionals guide and engage prospects and customers, and complete online tasks. They have raised over $90m in VC funding from some of the greats of the industry such as Rory O’Driscoll @ Scale Venture Partners and the team at Insight Venture Partners. As for Dan, prior to Walkme, he spent time at HP as a software engineer and before that spent 5 years in The Israeli Army’s elite computing unit.

In Today’s Episode You Will Learn:

  • How did Dan made his way from the elite computing unit of the Israeli army to San Francisco to found Walkme?
  • What does Dan believe are the most important metrics to assess the growth and potential of a SaaS startup? What does Dan believe is a good customer payback period?
  • What does Dan consider a good retention rate? How does Dan calculate sales rep productivity? What metric would suggest a successful rep and at what level should one be concerned?
  • What is the KPI that Dan uses to measure customer success? When is the right time to hear your first CS rep?

60 Second SaaStr

  1. What does Dan know now that he wishes he had known at the beginning?
  2. Fave SaaS reading material?
  3. When is the right time for startups to look to acquire other startups?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

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Dan Adika

Brad Feld is one of the world’s leading VCs having Co-Founded Foundry Group, Brad has made investments in the likes of Zynga, Makerbot and Fitbit, just to name a few. Brad is also Co-Founder of Techstars, one of the world’s most prominent startup accelerators, whose portfolio companies have raised over $1.3bn in funding. If that wasn’t enough Brad is also a best selling author having co-authoured Venture Deals: Be Smarter Than Your Lawyer and VC and Startup Communities: Building An Entrepreneurial Ecosystem In Your Community.

In Today’s Episode You Will Learn:

  • How Brad made his way into the world of VC and came to found Foundry Group?
  • Brad has previously stated that companies can be segmented into 3 different core components? What does he mean by this? How can startups be structured internally for scalability?
  • Why does Brad hate the word culture? How should culture be viewed and approach internally within startups?
  • How has Brad seen his personal development with regards to being a board member? What has he got better at? What does he believe makes a great board member?
  • Why is CAC the easiest metric to game in SaaS? How should the CAC/LTV ratio be approached? How can entrepreneurs use this to attract VC investment?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

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Brad Feld

Dan Burkhart is the Founder & CEO @ Recurly, the startup powering much of the subscription success, trusted by the likes of Twitch, CBS Interactive and Hubspot just to name a few. They have raised over $20m in VC funding from leading investors including Greycroft, Freestyle, Harrison Metal and more. As for Dan, his background spans 14 years with the likes of eBay and NBC Internet in the marketing, business development and strategic partnership realm.

In Today’s Episode You Will Learn:

  • How did Dan make his way into the world of SaaS and come to found Recurly?
  • How does Dan perceive a good CAC/LTV ratio? Does he agree with the hallowed 3:1 often cited by founders and investors?
  • How does Dan manage and measure customer churn? How does he approach regrettable and non-regrettable customer churn?
  • What is the post-mortem analysis of customer churn? How does Dan insert an element of accountability without creating a sense of churn?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Dan Burkhart

Scott Friend is a Managing Director @ Bain Capital Ventures where he has made investments in the likes of Jet and Rent The Runway. Scott joined Bain Capital Ventures in 2006 after selling the company he co-founded, ProfitLogic, to Oracle. At ProfitLogic, Scott saw the immense scaling of the company from its initial three founders to a 300 person global software and solutions business serving the retail industry. As a result, in 2005, Scott was named a winner of the Ernst & Young “Entrepreneur of the Year Award”.  Following the acquisition, Scott was Chairman of the Executive Advisory Board and VP of Marketing and Science for Oracle Retail.

In Today’s Episode You Will Learn:

  • How did Scott make the transition from building a 300 man SaaS startup, ProfitLogic to being a VC with Bain Capital Ventures?
  • What are the 3 fundamental ways SaaS has changed over the last decade? What does this mean for SaaS founders and investors today?
  • What is the single most important metric for Scott when evaluating a SaaS investment opportunity? Why is this and how has that thought process changed?
  • How can startups optimise for sales efficiency? Where does Scott see most startups make mistakes in this field?
  • When is the right time to hire your first customer success rep? Does it have to be embedded within the founding team? How can startups look to scale this and analyse risk over time?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Scott Friend



Mat Ellis is the Founder & CEO @ Cloudability, the startup that provides cloud cost efficiency at scale and they have raised close to $40m in VC funding including from our good friends at Foundry Group and Data Collective. As for Mat, prior to Cloudability, Mat held executive positions with four startups, and key technology roles at Frito-Lay, Pepsi Cola and Goldman Sachs and he currently sits on the boards of the Oregon Entrepreneurs Network and the Technology Association of Oregon.

In Today’s Episode You Will Learn:

  • How did Mat make the move from the UK to SaaS startup founder in Portland, Oregon?
  • How has Mat seen elements change within the business when moving through the stages of company growth? What were the challenges when going through these strategic inflection points?
  • At present, many SaaS founders are looking to hire COOs, what does Mat believe about this hire? When is the right time to make the hire? What should one look for in their first COO?
  • How does Mat assess the balance of sustainability and growth? How does Mat balance between this tough line? What are the inherent challenges?
  • What are Mat’s thought on culture maintenance when startup move into hypergrowth? What is core to retain this startup culture with the scaling through stages?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Mat Ellis

Peter Gassner is the Founder & CEO @ Veeva Systems, the industry cloud for life science systems. With just $4m in capital raised, Peter has taken Veeva to almost $500m in ARR and a prominent force in the rising tide of enterprise SaaS. As for Peter, prior to Veeva, Peter was a Senior Vice President of Technology at Salesforce where he experienced the successful IPO of the company and their rise into the most successful SaaS platform in the industry. Before Salesforce, Peter was with PeopleSoft for 9 years where he led a team of 450 professionals to support PeopleSoft’s technology platform. I do also want to say a big thank you to Jason Lemkin for the intro to Peter today without which the episode would not have been possible.

In Today’s Episode You Will Learn:

  • How did Peter make the move from Salesforce to founding one of the leaders in SaaS, Veeva?
  • Why did Peter not want to be CEO in the beginning? What was the catalyst for his changing mindset? How has view of CEOship evolved over the Veeva journey?
  • How does Peter assess the attractiveness of a market? What are the 2 questions Peter asks before going into a market? Is it wrong to move into smaller adjacent markets?
  • How does Peter assess the suitability of potential board members? What does he mean when he says all founders should use the ‘grocery store rule’?  
  • What is required to close 7 figure enterprise deals? How can sales teams look to build this relationship with large co’s in a natural and non-transactional way?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Daniel Ruch is the Founder and CEO @ Rocketrip, the startup that reduces travel spend by rewarding employees to save. They have backing from some incredible investors including the likes of Bessemer Venture Partners, Canaan Partners and Y Combinator. Prior to Rocketrip, Dan was a VP in Europe for Tremor Video and before that he held several director and managerial level positions at TACODA until TACODA’s sale to AOL.

In Today’s Episode You Will Learn:

  • How did Dan make his way into the world of SaaS and come to found Rocketrip?
  • How important is accountability for the founder and CEO? How do you convey this commitment and responsibility to the team? Are there any downsides?
  • At what stage does Dan believe the generalist transitions to the specialist? How has Dan seen his team evolve from stage to stage? What have been the challenges within each stage?
  • How does Dan approach hiring strategy? How does he look to determine people/company fit? Dan has said before that he ‘would not hire without a track record’, why is this?  
  • How does Dan view internal budgets? What are the fundamentals to cost saving within the business? How does Dan think one can cut cost without lowering morale?

60 Second SaaStr

  1. What is Dan’s fave SaaS reading material?
  2. What does Dan know now that he wishes he had known at the beginning?
  3. Carrot or stick, what does Dan prefer to implement?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Dan Ruch

Alex Rosen is a Managing Director with IDG Ventures where he focuses on investments in cloud infrastructure, SaaS applications, ad tech, and consumer marketplaces. Alex currently serves as board director at Chubbies, Krux, MindMeld, Minted, Smartling, Tempered Networks, and Uplift. He also led IDG Ventures’ investments in multiple companies including Appboy, Datanyze, Indiegogo, Nuzzel, The League and many more incredible companies. Previously, he was a General Partner at Sprout Group, where he was head of the Internet and Software group. Huge thanks to the team @ Sapphire Ventures for the intro to Alex today.

In Today’s Episode You Will Learn:

  • How did Alex make his way into the world of SaaS investing and come to be Managing Director @ IDG?

  • SaaS businesses can be massively affected by changes in a few very small data points. So what would you say is one of the single most important metric points?

  • What is a booking?  How should we break it down into the 3 different MRRs? What element of those metrics do you want to see growing?
  • How important a role does unit economics play? What are the couple of forms: customer + sales person? How much ARR should a good sales rep add to in ARR in relation to comp?
  • What is negative churn? How can you take a customer you have already sold and make more money from them? Upsell or cross-sell? What does this to the pricing axis? Why do you want more than 1 axis?

60 Second SaaStr

  1. What does Alex know now that he wishes he had known in the beginning?
  2. What are the greenfield opportunities in SaaS for Alex?
  3. What is Alex’s fave SaaS reading material?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Alex Rosen

Nadim Hossain is the Founder and CEO @ BrightFunnel, the startup that shows marketing true impact on revenue. They are backed by many past guests of the show including Matt Garratt @ Salesforce Ventures, Tim Kopp, and James Cham @ Bloomberg Beta. As for Nadim, prior to founding BrightFunnel, Nadim was VP of Marketing and Sales Development at PowerReviews, paving the way to a $170M exit. He was also a product marketing executive at Salesforce.com during their hyper-growth years.

In Today’s Episode You Will Learn:

  • How did Nadim make his way into the world of SaaS and come to found BrightFunnel?
  • To what extent is marketing an art or a science in today’s data driven world? How can marketers use and analyse data to drive decision making?
  • How can founders determine which channels are a must have as opposed to a nice to have? What metrics should determine this? Does brand building not count in the revenue driven world today?
  • Nadim has previously said, ‘marketing is eating sales’. What does Nadim mean by this? How does Nadim evaluate the expansion of the marketing funnel?
  • What are the biggest mistakes B2B companies make in today’s environment? How can they rectify this and sustain a brand that will deliver for the long term?

60 Second SaaStr

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Nadim Hossain

Michael Pryor is Co-Founder & CEO @ Trello, now Head of Product with Trello at Atlassian following their recent acquisition. For those that do not know, Trello lets you work more collaboratively and get more done. Prior to the acquisition they raised from some of the best in the business including the likes of Spark Capital, Index Ventures and Box Group. Michael is also a board member at StackOverflow.

In Today’s Episode You Will Learn:

  • How did Michael make his way into the world of startups and come to found Trello?
  • What does Michael believe is fundamental to making a market transition successfully? What were the challenges of the early market transition with Trello?
  • What does Michael believe are the 3 key elements that make a great CEO? How does Michael approach the element of cash burn? Does Michael agree for the need of sustainability within growth?
  • How does Michael look to continually recruit the best talent? What are the secrets to running a 60% remote workforce so efficiently?
  • How did the Atlassian deal come about? What was the thought process behind the sales vs raise more venture funding? How did Michael broach the process with regards to transparency within the team?

60 Second SaaStr

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

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Michael Pryor

Matin Movasatte is the Founder and CEO @ Heap. the startup that provides analytics infrastructure to automate away the annoying parts of user analytics. They have raised funding from some of the best in the business including our friends and former guests of The Twenty Minute VC including Pejman Nozad, Alexis and Garry @ Initialized, Josh Reeves at Gusto, Redpoint and more incredible investors. As for Matin, prior to Heap Matin was a product manager at Facebook and spent time at both Google and Mozilla. I would like to say a big thank you to Jason Lemkin for the intro today.

In Today’s Episode You Will Learn:

  • How did Matin make his way into the world of SaaS having been at Facebook and Google?
  • What were Matin’s biggest takeaways from seeing how Facebook operate? What were the pros and cons of their operations? How has this influenced how he builds Heap today?
  • Why does Matin believe that you should always sell your product before it is done being built? What benefits does this have in terms of pricing and iteration? What are the dangers of asking for payment upfront?
  • Why does Matin think it is crucial to hire your customer success team before your sales team? How do customer success drive customer acquisition?
  • What does Matin mean when he says that “product organisation fit” is so important? How can startups determine the fit? What can be done to optimise this?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Matin Movasatte

Didier Elzinga is the Founder & CEO @ CultureAmp, the world’s most powerful employee feedback and analytics platform. They have raised funding from some of the best in the business including the likes of Index Ventures, our friends at Felicis Ventures and Blackbird Ventures. As for Didier, he previously co-founded technical academy award winning Rising Sun Research and is non-executive director at Tourism Australia, the Atlassian Foundation and Slingsby Theatre. I also have to say a huge thank you to Ilya @ Index and Niki @ Blackbird for the intro, without which the show would not have been possible.

In Today’s Episode You Will Learn:

  • How did Didier make his way into the world of SaaS? What was the a-ha moment for him with CultureAmp?
  • What were Didier’s biggest takeaways from watching Scott and Mike build Atlassian? How did that affect and alter how he structured CultureAmp?
  • How does Didier evaluate product market fit? What are the signs? What metrics determine whether you have it or you do not? Why did Didier decide to bootstrap until $1m ARR?
  • Why does Didier believe there is so little innovation in the go to market strategies of today? What would he like to see change and where does he see opportunity?
  • Why does Didier not believe in paying sales teams commission? How does this affect his ability to hire? How does this affect the internal compensation structure of the firm?

60 Second SaaStr

  1. Didier’s Fave SaaS resource?
  2. What does Didier know now that he wishes he had known at the beginning?
  3. What has been the most challenging element of the CultureAmp journey?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Didier Elzinga

Fayez Mohamood is the Founder and CEO @ Bluecore, the company that is transforming the way eCommerce marketers use data and automation to communicate with customers. They have raised nearly $30m in funding from some of the best in the business and past guests of the show including the teams from FirstMark Capital and Felicis Ventures just to name a few. As a result they have enjoyed some rapid scaling having seen the team grow from 50 to over 100 in just 10 months. As for Fayez, prior to Bluecore he was Head of Product at BigDoor and before that he founded, Gameday Tycoon, a fantasy sports game that runs on Facebook.

In Today’s Episode You Will Learn:

  • How did Fayez make his way from fantasy sports game to successful SaaS founder with Bluecore?
  • To what extent does Fayez consider B2B marketing an art or a science with the rise of data? How can SaaS startups use data to drive conversion and upsell? What metrics does Fayez hone in on?

  • What 2 methods does Fayez use to harmonise the sales and marketing team? How can these teams be structured to ensure for a clear communication channel and culture of transparency?
  • With the team growing from 30 to over 100, what does the hiring process look like for Fayez? How has this altered and developed over time? What have been the big lessons in the rapid scaling of the team?
  • How does Fayez view efficiency within organisational structures? What must founders watch out for in the scaling process of their companies?

60 Second SaaStr

  1. Advantages and disadvantages of being a SaaS firm in the US?
  2. Fayez’s fave SaaS reading material?
  3. What does Fayez know now that he wishes he had known when he started?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Fayez Mohamood

Aaron Levie co-founded Box with three high school friends in 2005 when they discovered there wasn’t a modern solution for sharing and collaborating on work.They created Box to provide businesses with an easy way to share, access and manage information with enterprise-grade security, compliance and governance.Eleven years later, Box has been adopted by nearly 65% of the Fortune 500 and has nearly 70,000 paying business customers. The company went public in January 2015, and remains one of the fastest growing enterprise software companies.

In Today’s Episode You Will Learn:

  • How did Aaron with 3 friends from high school come to found one of the fastest growing enterprise software companies in Box?
  • How does Aaron view the convergence of enterprise and consumer products in the coming years? How does this convergence effect IT providers?
  • How does Aaron view transparency within organisations? How does this affect information flow? What must CEO’s consider when contemplating transparency within their organisation?
  • How does Aaron evaluate the inflection points in the growth of Box? What were the challenges in overcoming these hurdles? How did he have to change as a CEO to combat these changes?
  • What does the rise of AI mean for businesses and enterprise? What does the rise of VR allow the enterprise that was not previously possible? How do these emerging technologies affect the product and strategic roadmap at Box?

60 Second SaaStr

  1. Aaron’s favourite SaaS reading material?
  2. What will it take for Box to be 10x from here?
  3. What does Aaron know now that he wishes he had known in the beginning?
  4. What does Aaron spend most his time on that he would like to change?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Aaron Levie

Luke Retterath is the Director of Demand Generation @ Duo Security, the most loved company in security. They have the backing of some of the best investors in the business including Benchmark, Redpoint, Google Ventures and True Venture just to name a few. As for Luke, his role is to develop, execute, and manage demand generation programs assessing the effectiveness of all marketing programs as well as defining goals, metrics and ROI’s for the differing programs.

In Today’s Episode You Will Learn:

  • How did Luke make his way into the world of SaaS and come to found unicorn startup, Namely?
  • What are the 3 practical tests Luke uses to assess demand gen candidates in the hiring process? What are the right questions to ask? Is it right to look for badges on the CV?
  • Once the demand gen team is in place, how do we get the team jump started? Where should the focus be placed?
  • What are the 5 things that have helped drive growth at Duo? How can founders implement these into their demand gen strategy to 3x revenue for 3 years?
  • How should one plan and forecast when it comes to demand gen? How does Luke approach the topic of MQLs? How does this change for the inside sales team?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Douglas Hanna is the GM of the Developer Platform @ Zendesk, one of the world’s fastest growing SaaS startups. Before joining Zendesk, Douglas was the Founder & CEO @ Help.com where he grew the business from 1 to 16. Prior to Help, Douglas was the CEO of A Small Orange, the web hosting firm that was acquired by Endurance International Group where Douglas was on the Executive team when they went public on the NASDAQ.

In Today’s Episode You Will Learn:

  • How did Douglas make his entry into the world of SaaS and Zendesk?
  • What were the big adjustments that Douglas had to make from founding and working in smaller companies to working at Zendesk? What is the core to making the successful move?
  • How can companies go about building a platform? What are the fundamentals to consider once you have decided on the platform approach? What are the challenges?
  • How can a startup measure the success of their platform? What are the benchmarks and metrics that must be observed? How does testing and iteration play a role in platform success?
  • How does Douglas approach the go to market element with regards to platforms? How has the world of platform go to market changed in the world of omni-channel?

60 Second SaaStr

  1. Biggest mistake companies make with their platform approach?
  2. Fave SaaS reading material?
  3. What does Douglas know now that he wishes he had known at the beginning?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Douglas Hanna

Jonathan Lehr is the Co-Founder and Managing Director of Work-Bench, where he focuses on early stage enterprise technology investments in areas including big data analytics, machine learning, data-defined security and more. Prior to Work-Bench, Jon founded the NY Enterprise Technology Meetup in January 2012 and organizes monthly meetups of the 5,000+ person group as a way to promote collaboration for the enterprise tech ecosystem in New York. Jon has also worked at Morgan Stanley on the Office of the CIO team in IT. In that capacity, he partnered with internal technology clients to facilitate the selection and on-boarding of emerging technology vendors. He has also written about enterprise technology trends for publications such as The Wall Street Journal’s CIO Journal and TechCrunch.

In Today’s Episode You Will Learn:

  • How did Jonathan make his way into the world of enterprise investing with WorkBench?
  • Jon has previously said that enterprise tech is like chess, so what are the rules to play by? What can startups do to increase their chance of winning the game?
  • How can startups build scalable and natural relationships with decision makers in large enterprise clients? What are the fundamentals to doing this successfully? What does this conversation look like?
  • What does the buying decision making process look like in large corporates? How does that differ from space to space? How does that affect the sales cycle?
  • Why is NYC the best place in the world to start an enterprise tech company? What are the pros and cons of being in NYC?

60 Second SaaStr

  1. Greenfield opportunities in enterprise technology?
  2. What does Jonathan know now that he wishes he had known at the start?
  3. Jonathan’s fave SaaS reading material?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Jonathan Lehr

JD Peterson is CMO of Trello where he heads the company's marketing and customer service teams. A true child of Silicon Valley, J.D. has been helping startups for nearly 20 years.  Before Trello, he held positions as the CRO and interim CEO at Scripted, the VP of Marketing at Zendesk, and the VP of Products at Marketo. JD takes pride in building world-class teams, helping companies accelerate growth, and ensuring the customer remains at the center of every strategic effort.  

In Today’s Episode You Will Learn:

  • How did JD make his slightly unconventional entrance into the world of SaaS?
  • Having picked Marketo and Zendesk, what does JD assess when picking companies? Once picked, how does JD evaluate culture? How does JD measure this?
  • How does JD approach lead qualification? How does JD measure the effectiveness of lead generation, revenue or amount of leads? How does JD unify the sales and marketing team?
  • JD has previously said that now is ‘the best but hardest time to be a marketer’. Why is this and what is behind this thesis? What are the pros and cons of the data driven marketing world? What are the commonalities among the best marketeers?
  • JD has seen many companies scale into hyper-growth, when does JD believe is the right time to hire and expand aggressively? What roles should be filled first? What does JD optimize for in the hiring process? When is the transition point needed to have a VP?

60 Second SaaStr

  1. Is SaaS marketing B2B or B2C?
  2. What does JD know now that he wishes he had known in the beginning?
  3. Biggest mistake companies are enacting with their current marketing plans?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

JD Peterson




Tien Tzuo is the Founder and CEO @ Zuora, one of the fastest growing SaaS companies that has been at the forefront of the rise of subscription business models. They have funding from some of the best in the business including the likes of Benchmark, Sequoia, Redpoint and Marc Benioff, just to name a few. As for Tien, before Zuora, Tzuo was one of the 'original forces' at salesforce.com, joining as employee number 11. In his 9 years at salesforce.com, served in numerous different roles including as Chief Marketing Officer for two years, and most recently as Chief Strategy Officer.

In Today’s Episode You Will Learn:

  • How did Tien make his way from being an early employee at Salesforce to founding Zuora?
  • What were the big takeaways for Tien from seeing the meteoric rise of Salesforce? How has that experience moulded his running and strategy with Zuora today?
  • What does Tien see as the fundamental benefits of a subscription model? What products and services does it work best for? What are the keys to assembling this model successfully?
  • Tien has previously referred to scaling as ‘the climb’. How does he approach this analogy What was the most challenging element of scaling for Tien? How did he overcome it?
  • Tien has previously said that market strategy is the $100m question all founders must ask. So how does Tien approach go to market? What are the fundamentals to think when considering different go to market options?

60 Second SaaStr

  1. Biggest mentor and how the relationship came about?
  2. What does Tien know now that he wishes he had known in the beginning?
  3. Highlight of the Zuora journey so far?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Tien Tzuo

 

Lexi Reese is the Chief Customer Experience Officer at unicorn startup, Gusto and is one of the top female executives in Silicon Valley. Lexi’s passion for serving customers was sparked by her early career in microfinance as a public policy advocate with ACCION International—giving loans to people living in poverty to start their own ventures. She later worked at Google for eight years, most recently serving as Vice President of Programmatic Sales and Strategy globally. Lexi also started the Cambridge AdWords team for Google's small business organization. Now at Gusto, Lexi ensures that Gusto is continuously going above and beyond to serve all customers.

In Today’s Episode You Will Learn:

  • How did Lexi make her way from the world of Google and Facebook to SaaS with Gusto?
  • What were the biggest takeaways from spending 8 years at Google and seeing the immense hyper-growth there? How has Lexi applied those learnings to Gusto today?
  • How does Lexi look to put the ‘customer first’ thesis into practice? What does this look like in reality and from day 1?
  • How can one maintain such high levels of customer service with an ever increasing customer base? How can one insert elements of repeatability to make this easier?
  • Question from Hunter Walk: How do you fundamentally measure customer satisfaction? What benchmarks do you calibrate against to consider success?

60 Second SaaStr

  1. What does Lexi know now that she wishes she had known in the beginning?
  2. Most challenging aspect of Lexi’s role?
  3. Question from Tien @ Zuora: How do you look to avoid the hype culture that pervades the valley?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

 

Eric Yuan is the Founder & CEO @ Zoom, the video and web conferencing service that just last week raised $100m in venture funding from Sequoia Capital. Prior to founding Zoom, Eric was Corporate Vice President of Engineering at Cisco, where he was responsible for Cisco's collaboration software development. As one of the founding engineers and Vice President of Engineering at WebEx, Eric was the heart and soul of the WebEx product from 1997 to 2011. Eric proudly grew the WebEx team from 10 engineers to more than 800 worldwide, and contributed to revenue growth from $0 to more than $800M. Eric is a named inventor on 11 issued and 20 pending patents in real time collaboration.

In Today’s Episode You Will Learn:

  • How did Eric make his way into the world of SaaS? What was a-ha moment and founding story of WebEx?
  • How does Eric think about building products, customer first? What does that mindset and approach look like What are the main questions to ask? What are the challenges in doing so?
  • How should one approach growth with startups? Is growth ever in need of control? If so, what can be done to control growth? How can this be done without angering investors?
  • Eric has said before that founders must ‘spend more and burn less’. What does he mean by this? What does that look like in reality? What should be the main focus?
  • Does Eric agree with the notion that founders always undersell? How does Eric approach the situation of leaving money on the table? What are the challenges of doing so?

60 Second SaaStr

  1. What does Eric know now that he wishes he had known at the beginning?
  2. Eric’s Fave SaaS Reading Material?
  3. Biggest advice to SaaS founders?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Eric Yuan

Jason Lemkin is the Founder and VC @ SaaStr, or more accurately put Jason is a 2x founder, 1x VC, and constant SaaS enthusiast. He led or sourced the first VC investments in many leading enterprise/SaaS start-ups, Greenhouse.io, Pipedrive, Algolia, Talkdesk, RainforestQA, Automile, and more. He is also an advisor or smaller investor in Showpad, FrontApp, Influitive, BetterWorks, and other SaaS leaders. Jason has co-founded two successful start-ups selling to the enterprise.  Before SaaStr and VC investing, he was CEO and co-founder of EchoSign, the web’s most popular electronic signature service, from inception through its acquisition by Adobe Systems Inc. He then served as Vice President, Web Services at Adobe, where he oversaw the growth of EchoSign and Adobe Document Services to $50,000,000 in ARR in 2012 and $100,000,000+ ARR in 2013. Prior to EchoSign and Adobe, he co-founded one of the only successes in nanotechnology, NanoGram Devices, which was acquired for $50m just 13 months after founding. Other than SaaS he is like me, no known hobbies.

In Today’s Episode You Will Learn:

  • How did Jason make his way into the world of SaaS and come to be Founder and VC @ SaaStr?
  • ACV: What levels of ACV and characteristics suggest potential for a unicorn? How does Jason look to help founders attain higher ACVs? Why is stay focused horrible advice with regards to increasing your ACV with differing customer demands?
  • Does Jason believe that founders always undersell? What advice would Jason give to founders that are nervous to ask for more? What customer response would excite Jason and what would make him concerned?
  • Jason has previously said that ‘founders have to be 110% committed to sales’. What does this mean? How does this look when assessing a founder? Should founders be happy to pay their sales hires more than them? How quickly should the payback period be on these reps?
  • Jason has also previously said that some founders financials are ‘simply ridiculous’. What makes him say this? What financials are fundamental to have very accurately pin pointed? Why is 100% gross margin impossible?

60 Second SaaStr

  1. Why does Jason like it when startups have clients that are not in tech?
  2. What does Jason know now that he wishes he had known at the beginning?
  3. What should SaaS founders look for in their investors?
  4. Why does Jason only invest out of the SaaStr community?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Jason Lemkin is the Founder and VC @ SaaStr, or more accurately put Jason is a 2x founder, 1x VC, and constant SaaS enthusiast. He led or sourced the first VC investments in many leading enterprise/SaaS start-ups, Greenhouse.io, Pipedrive, Algolia, Talkdesk, RainforestQA, Automile, and more. He is also an advisor or smaller investor in Showpad, FrontApp, Influitive, BetterWorks, and other SaaS leaders. Jason has co-founded two successful start-ups selling to the enterprise.  Before SaaStr and VC investing, he was CEO and co-founder of EchoSign, the web’s most popular electronic signature service, from inception through its acquisition by Adobe Systems Inc. He then served as Vice President, Web Services at Adobe, where he oversaw the growth of EchoSign and Adobe Document Services to $50,000,000 in ARR in 2012 and $100,000,000+ ARR in 2013. Prior to EchoSign and Adobe, he co-founded one of the only successes in nanotechnology, NanoGram Devices, which was acquired for $50m just 13 months after founding. Other than SaaS he is like me, no known hobbies.

In Today’s Episode You Will Learn:

  • How did Jason make his way into the world of SaaS and come to be Founder and VC @ SaaStr?
  • ACV: What levels of ACV and characteristics suggest potential for a unicorn? How does Jason look to help founders attain higher ACVs? Why is stay focused horrible advice with regards to increasing your ACV with differing customer demands?
  • Does Jason believe that founders always undersell? What advice would Jason give to founders that are nervous to ask for more? What customer response would excite Jason and what would make him concerned?
  • Jason has previously said that ‘founders have to be 110% committed to sales’. What does this mean? How does this look when assessing a founder? Should founders be happy to pay their sales hires more than them? How quickly should the payback period be on these reps?
  • Jason has also previously said that some founders financials are ‘simply ridiculous’. What makes him say this? What financials are fundamental to have very accurately pin pointed? Why is 100% gross margin impossible?

60 Second SaaStr

  1. Why does Jason like it when startups have clients that are not in tech?
  2. What does Jason know now that he wishes he had known at the beginning?
  3. What should SaaS founders look for in their investors?
  4. Why does Jason only invest out of the SaaStr community?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Leo Widrich is the Founder & COO @ Buffer, the Simple and powerful social media scheduling, publishing & analytics. They have raised funding from some of the best including Scott and Cyan Banister, Hubspot’s Dharmesh Shah, Hiten Shah and Eric Ries just to name a few. Now in today’s talk with Leo he breaks down his and the Buffer teams Top 10 Learnings in Growing to 10m ARR.

In Today’s Episode You Will Learn:

  • What are the 3 questions Leo asks his customers to understand them best? When is the right time to ask them? How should you follow up from this?
  • How to experiment with weekly masterminds? How do masterminds work? When is the right time to do them? What is important to remember in entering a mastermind?
  • How does Leo assess pricing structure? Why does he think it is important to experiment with different pricing? How do you do so without losing customers or trust?
  • Why does Leo advise startup founders to get advice from mentors with conflicting opinions? Why is this important and how should a decision be reached?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Leo Widrich

John Barrows is essentially the Godfather of Sales. We often have VPs of Sales from tech titans on the show but who trains those VPs and sales reps to be the best in the world at sales? That is where John Barrows comes in, with clients including Dropbox, Box, Marketo, Twilio and many more, John has amassed a wealth of knowledge and experience allowing him to provide the most proactive sales tips and strategies to optimise the sales process. If you have not checked out his blog, that really is a must and can be found here.

In Today’s Episode You Will Learn:

  • How did John make his way into the world of SaaS and more specifically sales optimisation?
  • What are the key points all reps must cover in their first calls with new leads? Why is expectation setting so crucial?
  • Why does John believe the best client to rep relationships are those that are equal? How can reps continue to provide value with every interaction?
  • In the case of leads going dark, how can sales reps engage with the lead to ensure conversion? What words must be avoided and how should this conversation be structured?
  • How can sales reps perfect the balance of being direct and being rude? How important is a summary email? What is the optimal structure and how should sales reps follow up on summary emails?

60 Second SaaStr

  1. The most common question asked to John by VPs of Sales?
  2. What are the benefits of Top Down prospecting?
  3. Do execs need structure?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

John Barrows

Michael Driscoll is the Co-Founder and CEO @ Metamarkets, the startup that provide interactive analytics for programmatic marketing. They have raised over $38m in VC funding from our good friends at Data Collective, Founder Collective, IA Ventures and more incredible investors. As for Michael, prior to Metamarkets, he started two other companies: Dataspora, a life science analytics company (acquired by Via Science in 2011), and CustomInk.com, an early pioneer in e-commerce. Fun fact: Michael is also a founding Partner of the previously mentioned VC fund, Data Collective.

In Today’s Episode You Will Learn:

  • How did Michael make his way from data lover to Silicon Valley SaaS Founder?
  • Why does Mike believe in the inherent value of customer focus and product focus? What are the measurable benefits of being so specialised?
  • Why does Mike believe it is so hard to be a cost leader in software? What are the fundamental challenges? What role does open source play in this?
  • How does Mike view the alignment of the sales and the engineering team? Is it possible to have a harmonious relationship between the two?
  • What should SaaS startup founders look for in potential seed investors? How can they determine whether they have these qualities? What should they look at in particular?

60 Second SaaStr

  • Mike’s fave productivity tools?
  • What most companies are doing wrong in their approach to data science?
  • What does Mike know now that he wishes he had known at the start?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Michael Driscoll

Auren Hoffman is best known for being the former CEO and Founder @ LiveRamp, the leading data onboarder that was acquired by Acxiom for $310m. Today’s talk focuses on the 5 core lessons Auren took from that incredible journey with LiveRamp. Auren was also an angel investor and board member at BrightRoll, prior to it’s $610m acquisition by Yahoo. Today, he is the CEO at SafeGraph, the startup that is unlocking the world’s most powerful data so that machines and humans can answer some of society’s toughest questions.

In Today’s Episode You Will Learn:

  • What is Auren’s thesis towards hiring all round athletes as opposed to position players? When do it make sense to do either? What stage of the company is right for which persona?
  • What are the two different types of sales personas? At what type of company should you hire a relationship driven sales team and then what type of company for a product driven sales team?
  • Why does Auren believe you should target a very small niche of the market? What are the benefits of such focus? How can you sell such a small market to VCs?
  • How does Auren perceive the future of enterprise software? How has the rise of bottoms up sales affected the SaaS environment? How many more SaaS companies and buyers of SaaS are there today, compared to 10 years ago?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Auren Hoffman

Algolia the robust search API that allows developers to integrate lightning fast, typo-tolerant search into their SaaS product. Out of the box, Algolia offers developers a powerful platform for building great search experiences. By owning the entire stack from engine to server, Algolia free up development teams to focus on adding intuitive search that delights users. This is perfect for existing search teams looking to spend less time on maintenance and infrastructure management and more time on user experience. For small SaaS teams, Algolia is a great investment on top of your existing stack that requires no specialist engineers. And you can learn more about how Algolia helps SaaS Scale Search and get started on their 14-day Free Trial at Algolia.com/SaaStrPodcast



David Hassell is the founder and CEO of 15Five, the leading web-based employee feedback and alignment solution that is transforming the way employees and managers communicate. They have backing from the likes of Matrix Partners, Point Nine Capital and many more leading investors. As for David, he was named "The Most Connected Man You Don't Know in Silicon Valley" by Forbes Magazine, David has also been featured in The New York Times, The Wall Street Journal, Inc., Entrepreneur, Wired, Fast Company, and the Financial Post.

In Today’s Episode You Will Learn:

  • How did David made his way into the world of SaaS and came to found 15Five?

  • How does David view competition? How should founders view additional competition to their space? What is the right response? Why did David choose such a public and deliberate fight back against one competitive attempt?
  • David has said before that is passionate about the meaning and purpose of the business vehicle. What does he mean by this? How does this affect his thinking toward management and organisational structure?
  • What are the keys to creating a harmonized, incentivized and happy culture for your business? How scalable is this approach and how has David seen his approach alter and develop with the growth of the company?
  • Why did David choose the more bootstrapped funding option over the traditional heavy reliance on VC funding? Which startups is this right for? How can founders know when is the right time to put the pedal to the metal?

60 Second SaaStr

  1. David’s fave productivity tools?
  2. David’s biggest mentor and how it came about?
  3. What does David know now that he wishes he had known at the start?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

David Hassell

Alex MacCaw is the Founder & CEO @ Clearbit, the startup that is building a suite of business intelligence APIs to help companies find more information on their customers in order to increase sales and reduce fraud. They have backing from some of the best early stage investors including the likes of First Round Capital, SV Angel, Intercom’s Eoghan McCabe, Hubspot’s Dharmesh Shah and many more incredible investors. As for Alex, as well as being a fellow Brit who loves tea, he also worked at the likes of Twitter and Stripe prior to founding Clearbit.

In Today’s Episode You Will Learn:

  • How did Alex make his way into the world of SaaS and came to found Clearbit in SF having grown up in the UK?
  • Should API driven companies have sales teams? Should they do outbound? What’s the most effective way to generate leads?
  • Alex has said before that the trouble is, ‘everyone is treating their customers the same”. What does he mean by this? How do the smart companies differ? How possible is it to address customer specific needs at scale?
  • How does this scalability alter when elements like freemium and self service models are added to the equation? How effective have freemium tools been for Alex as a lead gen to on board new customers?
  • Why did Alex choose the same pricing structure as the likes of Stripe and Twilio? What was the thought process behind this?

60 Second SaaStr

  1. How important is it for SaaS startups to be in SF?
  2. What does Alex know now that he wishes he had known when he started?
  3. Biggest mentor to Alex and how it came about?
  4. Fave SaaS reading material?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Alex MacCaw

Ryan Smith is the Founder & CEO @ Qualtrics, an online survey company with 1,200 employees and a valuation of more than $1bn. They have backing from some of the world’s best investors including the likes of Sequoia, Accel and Insight Venture Partners having raised a $150m Series B in 2014. As for Ryan, there are many awesome things, first, he has built Qualtrics from Utah allowing him to gain perspective outside of the traditional tech bubbles, second, he held off on attain VC funding for many years despite the common belief that it is necessary for unicorn growth and finally he has the most incredible work life balance I have seen and if you have not already you must check out this piece on him in Forbes, it really is a must.

 

In Today’s Episode You Will Learn:

1.) How Ryan made his way into startups and came to found Qualtrics?

2.) Sequoia’s Bryan Schreier states that Ryan’s success is due to running the company on ‘first business principles’. What does he mean by this? How does this affect the way Ryan runs Qualtrics?

3.) Why did Ryan decide to bootstrap the company for such a long time with the likes of Accel and Sequoia looking to invest? What are the benefits of retaining such control? What are the financial requirements to do so?

4.) What makes the best CEO’s? How do they view the internal structure of the company? How do they perceive their role? How do they manage their day and optimise their time?

5.) How does Ryan look to instill ‘radical transparency’ in the organisation? What are the benefits of doing so? Can an organisation ever be too transparent? What are the challenges of such transparency?

David Rodnitzky is founder and CEO of 3Q Digital, a leading digital agency that was acquired by Harte Hanks in 2015. Prior to 3Q Digital, he held senior marketing roles at several Internet companies, including Rentals.com (2000-2001), FindLaw (2001-2004), Adteractive (2004-2006), and Mercantila (2007-2008). David currently serves on advisory boards for several companies, including Marin Software, MediaBoost, Mediacause, and a stealth travel start-up.

In Today’s Episode You Will Learn:

  • How did David enter the world of B2B SaaS marketing? What was the entry point for him?
  • What really is SaaS marketing? Is it more consumer or B2B like? How does this alter and develop with the growth of the company?
  • Before spending heavily on marketing, what gating factors should SaaS founders think heavily about before the big spend? Should this marketing plan be undertaken by an external firm or an internal team?
  • What market channels should a SaaS company consider as ‘must haves’ in today’s world, as compared to ‘nice to have’s’? How does David differentiate between the two?
  • We are always told if you cannot measure it, do not do it? How can SaaS companies measure the success and effect of their marketing campaigns? What are the key metrics that define success?

60 Second SaaStr

  1. Biggest mistake current SaaS companies are currently enacting with their marketing?
  2. Favourite marketing resources and tools?
  3. What does David know now that he wishes he had known at the beginning?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

David Rodnitzsky

Steve Garrity is COO and founder of Hearsay Systems the leading advisor-client engagement solution for the financial services industry. Hearsay have backing from the likes of Sequoia, NEA, Kleiner Perkins Partner, Mike Abbott and Path Founder, Dave Morin. Before founding Hearsay, Steve worked as an engineer at Microsoft Corporation in Seattle is a graduate of Stanford University with a BS and MS in Computer Science. While at Stanford, he was selected as a Mayfield Fellow in the Stanford Technology Ventures Program. During which, he joined Fortify Software as a product manager. Steve is also an investor in, and advisor to a number of Silicon Valley start-ups.

In Today’s Episode You Will Learn:

  • How did Steve made his way into the world of SaaS from the world of Microsoft?
  • How does Steve approach the management around his engineering team? How does Steve balance management of engineers while still allowing creativity? Are there dangers of giving engineers freedom?
  • Is it possible to have both a happy engineering and sales? How does Steve look to harmonise the team? Is it not contra popular theory to have different cultures for different segments of the team?
  • Why does Steve believe that executive coaching is an almost universal requirement? How does Steve justify that to the board?

60 Second SaaStr

  1. Steve’s Biggest Productivity tools?
  2. What does Steve now know that he wishes he had known at the start?
  3. The biggest mistake SaaS companies are enacting with their social media strategies?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Steve Garrity

Peter Reinhardt is the Founder and CEO @ Segment, the startup that allows you to collect all of your customer data and send it anywhere and they count some of the biggest and best companies in the world as customers including the likes of Reuters, HotelTonight, New Relic and Atlassian. They do not only have some of the world’s leading customers but some of the world’s best investors with the likes of Accel, Thrive and Kleiner Perkins participating in their latest $27m Series B. I would like to say a huge thanks to Grant Miller @ Replicated for the intro to Peter today.

In Today’s Episode You Will Learn:

  • How did Peter make his way into the world of SaaS and come to found Segment?
  • How does Peter define product market fit? Does he agree with Justin Kan in stating that it is when you get the first 10 customers that are unaffiliated?
  • Why does Peter believe product market fit suffers when related to Job’s idea of the reality distortion field? What is so damaging and what should founders look to avoid?
  • How do technical and non-technical co-founders differ in their approach to product market fit? How do their expectations, desires and reactions alter to differing levels of uptake?
  • How did Peter navigate the process of scaling prices with time? Was he nervous when doing so? What does Peter advise founders when attempting significant price increases?

60 Second SaaStr

  1. What were the biggest takeaways from YC?
  2. What does Peter know now that he wishes he had known at the beginning?
  3. The biggest challenge in building out the team?
  4. Favourite SaaS resource or reading material?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Peter Reinhardt

Seth Besmertnik is the Co-Founder & CEO @ Conductor, the company that boasts the biggest customer list in their category including more than 500 Fortune and Internet Retailer 500 brands like Under Armour, Citi and FedEx with their web presence management and SEO. With this incredible success, the company has been ranked 13th fastest growing software company in the US and the 3rd Best Place To Work in NYC. They have also raised funding over $60m from some of the best investors on the east coast in the form of Matrix Partners and FirstMark Capital just to name a few. I would like to say a huge thanks to Fayez @ Bluecore for the intro to Seth today.  

In Today’s Episode You Will Learn:

  • How did Seth make his way into the world of SaaS? What was the a-ha moment for Conductor?
  • What does Seth mean when he says, ‘B2B companies need to build a weapon in their marketing’? How does this look in his approach? How does this differ according to differing startup budgets?
  • Previously, Meaghan Eisenberg @ MongoDB has said ‘the largest lift you are going to see is from your site’. Does Seth agree with this? How should we prioritise the site? What are the fundamentals to consider in terms of optimising conversion?
  • With the proliferation of content today, to what extent should B2B companies look to alternative platforms such as  Snapchat, Youtube and Instagram for content differentiation? What are the fundamentals to consider with platform diversification?
  • How does Seth suggest creating a culture of content creation in previously segmented cultures? How can this be done with actionable strategies to encourage non-marketing professionals to produce content?

60 Second SaaStr

  1. What does Seth know now that he wishes he had known before?
  2. Biggest advice on content creation for B2B SaaS companies?
  3. Fave SaaS reading material?
  4. Being a CEO vs Being a Founder
If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Seth Besmertnik

Kathryn Minshew is the Founder & CEO @ The Muse, named to Forbes’ 30 Under 30 in Media and Inc.’s 15 Women to Watch in Tech. Before founding The Muse, Kathryn worked on vaccines in Rwanda and Malawi with the Clinton Health Access Initiative and was previously at McKinsey. Kathryn has spoken at MIT and Harvard, appeared on The TODAY Show and CNN, and contributes on career and entrepreneurship to the Wall Street Journal and Harvard Business Review.

In Today’s Episode You Will Learn:

  • How Kathryn came to found The Muse? What was the a-ha moment for her?
  • Why did Kathryn introduce a SaaS business model into the traditionally, transactional model of recruiting? What were the benefits and how did it alter her go to market?
  • With no prior sales experience, how did Kathryn find the experience of running the sales team? What were the core takeaways? At what stage should the founder stop selling the product and hire a sales team?
  • Why does Kathryn believe you have to make the customer feel slightly uncomfortable to be successful? What did Kathryn look for in her initial sales hires? Why did Kathryn hire 3 reps to start with and not 2, as usually suggested?
  • How does Kathryn approach the customer success field at The Muse? When did Kathryn hire her first CS rep? What is Kathryn’s take on CS being involved in the sales process?
60 Second SaaStr
  1. What does Kathryn know now that she wishes she had known when she started?
  2. Biggest mistake SaaS companies are enacting with their recruiting process?
  3. Productivity tips and hacks?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Kathryn Minshew

Michael Sharkey is CEO & Co-Founder of Autopilot, the startup that allows you to automate customer journeys as simply as drawing on a whiteboard. Autopilot has funding from some of the best investors both in Australia and in SaaS with backing from the likes of Salesforce Ventures and Blackbird Ventures. Prior to founding Autopilot with his two brothers, Michael joined his brother Chris to grow start-up Stayz into a top Australian rental booking site which was acquired by FairFax Digital in 2006 and again by HomeAway for $225M in 2013. Michael also co-founded digital marketing agency Sharkey Media where he helped grow Australian startups. I would love to say a huge thank you to Matt Garratt @ Salesforce Ventures for the intro to Michael today.

In Today’s Episode You Will Learn:

  • How did Michael come to co-found Autopilot with his two brothers? What was the a-ha moment for him?
  • Why did Michael choose a self service model with Autopilot? How does this model affect their CAC? How does this model alter the outbound marketing strategy?
  • How does Michael approach the dilemma of variable or fixed pricing? Has Michael found that the lack of reliability around variable pricing causes customers concern?
  • With Michael interest in unit economics, why are we seeing many SaaS startups, Marketo and Eloqua, exiting with losses? What can founders do to adopt the unit economics first mindset? How does this attitude to unit economics affect attitudes to aggressive growth?
  • Michael focuses on 100% net retention, what does that process and strategy look like in practice? How does this commitment to 100% retention affect Michael’s management style and work processes?

60 Second SaaStr

  1. Biggest mentor to Michael and how it came about?
  2. What does Michael know now that he wishes he had known in the beginning?
  3. The biggest mistakes SaaS companies make with their email marketing processes?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Michael Sharkey

Robert Siegel is a Partner at XSeed Capital, one of the leading seed funds in the valley. At XSeed, Rob specialises on, you guessed it, all things from the wonderful world of SaaS and he sits on the Board of Directors of Cape Productions and Caller Zen. Robert is currently on the faculty at the Stanford Graduate School of Business where he teaches an array of topics that he led to His role as the Co-President Emeritus of Stanford Angels & Entrepreneurs. Prior to joining XSeed, Robert was General Manager of the Video and Software Solutions division for GE Security, with annual revenues of $350 million. Before that, Robert was Co-Founder & Chief Executive Officer of Weave Innovations Inc. (acquired by Kodak). If that was not enough Robert also served in various management roles at Intel Corporation, including an executive position in their Corporate Business Development division, in which he invested capital in startups that were strategically aligned with Intel’s vision. I would also like to say a huge thanks to Tien @ Zuora for the intro to Robert today.

In Today’s Episode You Will Learn:

  • How did Robert make his way into the world of SaaS? What was it about XSeed that made him want to make the transition from operations to VC?
  • We have seen many big SaaS exits in the last year with Marketo and Nutanix, does Robert think the time for big SaaS exits has come and gone? Have we moved to a world of consolidation?
  • How do companies both large and small need to react to this shift on a strategic level? How does this affect the internal infrastructure of larger companies?
  • For smaller startups, how should their attitude to competition change? How does this change Robert’s search process as an investor? How can smaller startups make themselves attractive acquisition targets?
  • How does Rob’s view of consolidation affect his excitement for mega returns in SaaS? How does it impact how Rob approaches valuation? How does this change Rob’s expectations of unit economics?

60 Second SaaStr

  1. Strategic investors: Good or Bad?
  2. What does Rob know now that he wishes he had known when he started?
  3. Fave SaaS resource or reading material?
  4. Greenfield opportunity in SaaS?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Robert Siegel

David Thompson is CMO at Domo, the company that allows customers to turn data into opportunities. David is a highly accomplished branding expert and recognized leader in demand generation, having served as longtime CMO of WebEx, where he named the company, helped create the cloud-based conferencing category and positioned the company for its IPO and subsequent buyout by Cisco. He also co-founded and served as chief executive officer of Genius.com, a leading SaaS marketing automation company, and he launched the Sales 2.0 Conference.

In Today’s Episode You Will Learn:

  • How did David make his way into the world of tech and SaaS pre-bubble? How did the bubble affect how David approached company building going forward?
  • What should all SaaS startups consider pre spending big on marketing? What should their core gating factors be? Is it always right to have an internal marketing team?
  • What are the must haves and the nice to haves in B2B marketing? Why is Facebook a must have or business branding today?
  • How can businesses accurately measure the success of their marketing and branding efforts? Is it all about revenue or is there external reputation metrics to consider?
  • On the whole, would David consider successful B2B branding closer to consumer or closer to enterprise marketing? What do the best in the enterprise class do?

60 Second SaaStr

  1. What are David’s favourite marketing tools?
  2. If David could recommend one book to SaaS founders what would it be?
  3. With the martech explosion: are we entering a world of consolidation?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

David Thompson

Daniel Saks is the Co-CEO of AppDirect, which he founded in 2009. AppDirect is the leading commerce platform for selling cloud services and at the firm, Daniel plays a key role in the growth and development of AppDirect, from attracting a leading team, to nurturing relationships with customers and partners. AppDirect has backing from some of the leading investors in the world including the likes of Foundry Group and J.P. Morgan. Prior to AppDirect, Daniel worked at Viant Capital, a boutique tech investment bank.

In Today’s Episode You Will Learn:

  • How did Daniel make the move from family business to SaaS founder? How did he get the business off the ground in the early days?
  • From working in his family business, what did Daniel observe about the buying patterns of businesses? What makes Daniel believe humans like to buy from humans?
  • Is it a problem that many of today’s software vendors lean on direct sales? What are the first steps to create a multi-channel approach? What does it take to support indirect sales channels such as affiliates and resellers?
  • What is Daniel’s 4 Step Playbook for optimising the distribution of software? What does it take to move past the early adopter audience into the hands of the wider market?
  • Why does Daniel believe that the promise of SaaS is yet to be fully realised? What excites Daniel with the rise of the cloud and the movement away from on-premise?

60 Second SaaStr

  1. When is the right time to hire your first customer success rep?
  2. What does Daniel know now that he wishes he had known at the beginning?
  3. Biggest challenge in the AppDirect journey and how Daniel overcame it?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Daniel Saks

Part 2 with David Skok, now David is a serial entrepreneur turned VC at Matrix Partners. He founded four companies: Skok Systems, Corporate Software Europe, Watermark Software, and SilverStream Software and did one turnaround with Xionics. Three of the companies he founded went public and one was acquired. In 2001 David joined Matrix Partners, who had backed his last two startups, as a General Partner. David’s successful exits as an investor at Matrix include: HubSpot, JBoss, AppIQ, Tabblo, Netezza, Diligent Technologies, CloudSwitch, TribeHR, GrabCAD, OpenSpan and Enservio. David currently serves on the boards of Atomist, CloudBees, Digium, Meteor, Namely HR, Salsify, and Zaius. You can also find David’s amazing blog here! Huge thanks to Hardi Meybaum and Jason Lemkin for the intro to David today.

In Today’s Episode You Will Learn:

  • What is negative churn? Why is it fundamental for SaaS startups to have a strong grasp of their negative churn?
  • How does negative churn affect the pricing axis? What can startups do if they have no alternative product to upsell to?
  • To what extent should founders be willing to engage in customisation in order to upsell a product? What are the dangers? What should founders be mindful of?
  • To what extent is up sell the responsibility of customer success? Should they have a hand in the sales process? What are the dangers and concerns?
  • How important is it for a startup to track their champion with the customer company? Does it matter if your champion leaves? What should you do if so?
60 Second SaaStr

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

David Skok

David Skok is a serial entrepreneur turned VC at Matrix Partners. He founded four companies: Skok Systems, Corporate Software Europe, Watermark Software, and SilverStream Software and did one turnaround with Xionics. Three of the companies he founded went public and one was acquired. In 2001 David joined Matrix Partners, who had backed his last two startups, as a General Partner. David’s successful exits as an investor at Matrix include: HubSpot, JBoss, AppIQ, Tabblo, Netezza, Diligent Technologies, CloudSwitch, TribeHR, GrabCAD, OpenSpan and Enservio. David currently serves on the boards of Atomist, CloudBees, Digium, Meteor, Namely HR, Salsify, and Zaius. You can also find David’s amazing blog here! Huge thanks to Hardi Meybaum and Jason Lemkin for the intro to David today.

In Today’s Episode You Will Learn:

  • How did David make his way into the world of SaaS? What was it about Matrix that made him want to make the transition from operations to VC?
  • Why are metrics so important? What role do they play in an organisation? How do good founders respond to questions on not achieving sales targets?
  • Why are SaaS businesses immune from being measured on standard financials like GAP financials? What metrics in SaaS really determine the trajectory of the business?
  • How can founders examine unit economics to determine whether they have a sustainable SaaS business?
  • How does David address sales rep productivity? How much in ARR should they be booking in relation to their annual comp package?
60 Second SaaStr

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

David Skok

Taro Fukuyama is Founder & CEO @ AnyPerk. Born and raised in Tokyo, Taro is a Y Combinator graduate with AnyPerk and part of the first Japanese team ever to be admitted to YC. He was also named one of Business Insider’s “Silicon Valley 100 Coolest People in Tech Right Now.”Fun fact, Taro co-founded AnyPerk in a Taco Bell car park! What a story! They also have investment from the likes of DCM, YC, Gary Vaynerchuk, previous SaaStr guest Nick Mehta and many more incredible people. I would also like to say a huge thanks to Jason lemkin for the intro to Taro today.

In Today’s Episode You Will Learn:

  • How did Taro make his way to San Francisco and come to found AnyPerk?
  • As a first time founder, how did Taro look to build out the management team? What were the inherent challenges and what did Taro look for in his core executive?
  • What are the 6 questions that will determine whether you have clarity in your organisation? Why is clarity so important to unify the team? What does this clarity allow?
  • What are the 5 steps to building a cohesive team? How can CEOs be both vulnerable and authoritative as a leader?
  • How should founders approach offsites? What is the necessary preparation? How should they be structured for optimal productivity? What can be done to ensure they produce meaningful outcomes?

60 Second SaaStr

  1. Favourite SaaS reading material?
  2. What does Taro know now that he wishes he had known at the beginning?
  3. The biggest mistake companies make with employee happiness?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Taro Fukuyama

Matt MacInnis is the Founder & CEO @ Inkling, the company that brings policies and procedures to life for your desktop workers. The company has backing from some of the best investors in the world with the likes of Sequoia, Felicis and Kapor Capital behind them. As for Matt, prior to Inkling, he spent 7 years at the one and only Apple Inc. I would also like to say a huge thank you to Taro Fukuyama, Founder @ AnyPerk for the intro to Matt.

In Today’s Episode You Will Learn:

  • How did Matt make his way into the world of SaaS and Inkling from Apple Inc?
  • Does culture in sales really matter? Is it not just about hitting the fucking number? What are the two opposing culture that exist in the world of sales team? Why is missionary always better?
  • How can a sales leader instill a competitive element into a missionary sales culture? What are the inherent challenges and how does Matt approach them?
  • Is it possible to have a fantastic sales and a fantastic engineering culture? How can the two live under the same roof and what needs to happen to ensure this works?
  • In terms of measurement, how can a founder know whether they have a strong culture? What are the signs and indications?

60 Second SaaStr

  1. Productivity Tools
  2. What does Matt know now that he wishes he had known in the beginning?
  3. Biggest mistake most SaaS companies are enacting with their sales process?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Matt MacInnis

Whitney Sales is the VP of Sales at TalentIQ, has been involved in bringing products to market and managing high growth sales teams for over a decade. She is the creator of the Sales Method, a strategic framework for launching products, which she used to help three companies earn a place on the Inc 5000 fastest growing companies list. Prior to joining TalentIQ, Whitney held executive positions at Wanelo and SpringAhead and currently serves as a mentor at StartX, Alchemist, and previous guest Acceleprise and a huge thanks to Michael Cardamone @ Acceleprise for the intro to Whitney today.

In Today’s Episode You Will Learn:

  • How did Whitney make her way into the world of SaaS and more specifically sales?
  • What are the 5 key criteria that founders need to consider before embarking on the sales process?
  • How specific and targeted should a customer profile be? How many profiles can they have? What are the best questions to determine the optimal customer segment?
  • How can founders identify which buyers are innovators? What tools are best for this? Once discovered, how should founders approach these innovators?
  • Founders learn about gaps in customer information from selling. So how close should the integration of content marketing and selling be in the early days?

60 Second SaaStr

  1. What are Whitney’s preferred tools for her tech stack?
  2. What does Whitney know now that she wishes she had known at the beginning?
  3. Does the proliferation of sales tools make it harder or easier?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Whitney Sales

Ryan Petersen is the Founder and CEO of Flexport, the freight forwarder for the internet age. Flexport recently raised a phenomenal $65m Series B from the likes of Founders Fund, First Round, Felicis, Bloomberg Beta, Yuri Milner, Susa Ventures and more incredible investors. With none other than YC founder Paul Graham stating ‘Ryan has the rare ability to not just satisfy the market but grow it’. Prior to Flexport, Ryan was Founder and CEO of ImportGenius.com, the largest provider of business intelligence to the import-export industry. A huge hand to Chad Byers @ Susa and Jason Lemkin for the intro

In Today’s Episode You Will Learn:

  • How did Ryan make her way into the world of SaaS and come to found Flexport?
  • How does Ryan view NPS? Why is he so bullish? Why is it the most important metric? What are the downsides to relying on NPS?
  • What is the optimal method to structure internal compensation structures? Why is compensation based on NPS and Net not effective and what are the dangers of this?
  • How can founders look to implement bottoms up decision making in their organisation? What are the benefits of this and what are the challenges to it’s implementation?
  • Ryan is hiring his first VP of Marketing? What should founders look for in their VP of Marketing? Why is now the right time and what challenges has Ryan faced in the process?

60 Second SaaStr

  1. Fave SaaS reading material?
  2. What does Ryan know now that he wishes he had known when he started?
  3. What has been his biggest learning throughout the Flexport journey?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Ryan Petersen

Josh Reeves is the Founder and CEO @ Gusto. Gusto reimagines payroll, benefits, HR, and personal finance and it is this reimagination that has led to their recent addition to the unicorn club with investors including Google Capital, Kleiner Perkins, Data Collective and General Catalyst, just to name a few. As for Josh, he was selected for the 2012 Forbes 30 Under 30 list. Prior to co-founding Gusto, he was the CEO and co-founder of Unwrap, a SaaS startup which was acquired in 2010, and he began his career as an early employee at Zazzle. I would also like to give a big hand to Jason Lemkin and Phil Libin for the intro to Josh today.

In Today’s Episode You Will Learn:

  • HR and Payroll is not sexy so how did Josh make his way into the industry and what was the a-ha moment for Gusto?
  • Josh has said before ‘he lives and breathes how a company is built.’ How has Josh looked to grow and develop his own internal organisation at Gusto? How does this vary with stage?
  • Josh has hired over 300 people at Gusto, how does he approach the interview process? What is the right way for employers to approach the ‘making offers’ stage?
  • How important does Josh feel it is to have an ownership culture and internal entrepreneurialism? How can this environment be fostered and developed?

60 Second SaaStr

  1. How employers can ensure new employees have an amazing first day?
  2. What does Josh know now that he wishes he had known when he started?
  3. The biggest mistake SaaS companies make with their HR and payroll organisation?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Josh Reeves

Jeff Fernandez is the Co-Founder & CEO @ Grovo, the enterprise learning solution that allows you to educate and empower your employees. At Grovo, Jeff oversees sales, investor relations, and the building of Grovo’s award-winning culture. Prior to founding Grovo in 2010, Jeff served as product manager at Clickable (acquired by Syncapse). From 2006 until 2009, he led business development and sales for Doostang (acquired by Universum Global), an online career networking community. Jeff is also a bit of a rockstar off the field getting the highest honours from Harvard penning his thesis on human performance and then playing semi pro football for the New York Rebels in 2008. I would also like to say a massive thank you to Greg Sands @ Costanoa Venture Capital for the intro to Jeff today.

In Today’s Episode You Will Learn:

  • How Jeff came to found Grovo? What was the a-ha moment for him?
  • Jeff is renowned to ‘lead from the heart’. What are the advantages of this as a CEO? How does this affect the company, the culture? What are the inherent challenges?
  • Question from Greg Sands: Jeff likes to ‘work the sales floor’, how does that work? What does Jeff actually do? What have been Jeff’s observations having seen the sales floor up close?
  • How does Jeff look to structure the compensation for his sales team? How does this vary with time and stage?
  • What does Jeff mean when he says ‘sometimes you have to go slow to go fast’? How does that play out in his management style?

60 Second SaaStr

  1. Jeff’s biggest productivity tips?
  2. Biggest challenge for Jeff in being CEO @ Grovo?
  3. What does Jeff know now that he wishes he had known at the beginning?

 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Jeff Fernandez

Sangram Vajre is the Co-Founder & CMO at Terminus, the leading account-based marketing platform. Prior to Terminus, Sangram was the Head of Marketing @ Pardo, prior to it’s acquisition by Salesforce. Sangram is also the brains behind the marvel that is Flip My Funnel which challenges the status quo of traditional B2B marketing practices and transform how B2B marketers approached driving revenue in their organization. You might remember in a recent episode Tim Kopp @ Hyde Park Ventures cited Sangram and his revolutionary approach with Flip My Funnel as one to watch. If that was not enough, Sangram is also the author of "Account-Based Marketing For Dummies".

In Today’s Episode You Will Learn:

  • How Sangram came to found Flip My Funnel and Terminus? What was the a-ha moment and origin story for Sangram?
  • Why does Sangram believe the funnel needs to be reinvented? Where are the inefficiencies? What can be done to optimise the funnel and what are the steps to do so?
  • How did Sangram establish such a strong brand in the B2B space on a shoe-string budget in such a short space of time? What tactics can be done to exert your authority over a domain?
  • How does Sangram look to create an ownership culture of internal entrepreneurs at Terminus? Why is it so important to try and hire people who know more than you?
  • Why did Sangram decide to hire a customer success rep before any other function? What did he look for in his first CS person? What does Sangram thinks is fundamental to being successful at CS?

60 Second SaaStr

  1. Biggest learning from founding and scaling Terminus?
  2. Sangram’s Favourite SaaS reading material?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Sangram Vajre

Matt Murphy is a Managing Director @ Menlo Ventures where he focuses on multi-stage investments across cloud infrastructure and AI-first SaaS applications. Since joining Menlo, Matt has led investments in Heap Analytics, Usermind, and Veriflow. Previously, Matt was a General Partner at Kleiner Perkins for over 15 years.  Matt was also an observer at Google (from initial investment to IPO), launched the iFund in ’08 (a collaborative initiative with Apple to build the defining applications on the iOS platform), and led KPCB’s investments in AutoNavi (Nasdaq: AMAP, 2010) and Aerohive Networks (Nasdaq: HIVE, 2014). Before joining KPCB, Matt worked at semiconductor startup Netboost (acquired by Intel) and prior to that at Sun Microsystems.

In Today’s Episode You Will Learn:

  • How Matt made his way into the world of VC and enterprise investing? What were his biggest takeaways from working alongside John Doerr @ Kleiner Perkins?
  • How is the enterprise investing landscape changing? What fundamental shifts have we seen and what have been the dominant repercussions of this?
  • Nakul Mandan stated that ‘we would see the 2nd wave of consumerisation of enterprise through business model’. Does Matt agree with this and what key trends is Matt most excited about in SaaS?

  • How does Matt look to evaluate early stage SaaS valuations? What are people fundamentally misvaluing and how should the topic be approached?
  • Is it harder now for SaaS companies to raise than ever before? What metrics does Matt look for in a Series A investment opportunity?  

60 Second SaaStr

  1. Matt's Fave SaaS reading material?
  2. What are the greenfield opportunities in SaaS today?
  3. What was Matt's biggest takeaway from working with John Doerr @ Kleiner Perkins?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Matt Murphy

Brandon Bruce is the Co-Founder and COO @ Cirrus Insight, the plugin for Gmail and Outlook that automatically updates Salesforce as you work. Cirrus is a bootstrapped startup with triple-digit yearly growth since it's founding 4 years ago and has grown from 2 co-founders in 2011 to a team of 55 people today. And I have to say a huge thanks to Aaron Ross, Author @ Predictable Revenue for the intro to Brandon today. Likewise, if you want to join me and Jason for mojitos at SaaStr Annual 2017 and also want an incredible 20% off ticket prices, then all you have to do is click here!

In Today’s Episode You Will Learn:

  • How did Brandon make his way into the world of SaaS and come to found Cirrus Insight?
  • What does Brandon mean he says he likes to take the road less travelled in Sales? What have been his learnings from his interactions on the front line of sales? How has it changed how he approaches sales?
  • How are Cirrus so efficient at events in terms of getting more leads, meeting and sales? What is the strategy going into events? How can we optimise this?
  • Speaking of events in general there, how does Brandon look to define prospect and buyer personas? How important is this for events? How narrow and specific do these personas have to be?
  • Brandon has stated before in the importance of learning and doing manual before automatic with the future in mind. What do he mean by this and how does it affect his roadmap and thought process to the future going forward?

60 Second SaaStr

  1. Favourite SaaS reading material?
  2. What does Brandon know now that he wish he had known at the beginning?
  3. The biggest challenge of running Cirrus and how Brandon looks to combat it?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Brandon Bruce

John Barrows is essentially the Godfather of Sales. We often have VPs of Sales from tech titans on the show but who trains those VPs and sales reps to be the best in the world at sales? That is where John Barrows comes in, with clients including Dropbox, Box, Marketo, Twilio and many more, John has amassed a wealth of knowledge and experience allowing him to provide the most proactive sales tips and strategies to optimise the sales process. If you have not checked out his blog, that really is a must and can be found here.

In Today’s Episode You Will Learn:

  • How did John make his way into the world of SaaS and more specifically sales optimisation?
  • How has John seen the sales landscape evolve? What has been the effect of the segmentation of roles pioneered by Salesforce?
  • What will be the catalyst that causes teams to shift from current sales methods and teams to AI replacing the sales team? What does this depend on?
  • How does John view the integration of sales and marketing? How does the rise of ABM change this?
  • How can sales reps perfect the balance of being direct and being rude? How important is a summary email? What is the optimal structure and how should sales reps follow up on summary emails?

60 Second SaaStr

  1. The most common question asked to John by VPs of Sales?
  2. What are the benefits of Top Down prospecting?
  3. Do execs need structure?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

John Barrows

John Gleeson is VP of Customer Success @ Affinio where John was employee #1. 2 years and a half years later, John is the VP of Customer Success following their Series A and has seen the team expand to over 40 people and have offices in New York, Toronto, Halifax and Ireland. John has written a special blog post just for SaaStr listeners today outlining his ultimate guide to customer success reading, it is my go to guide for customer success.

In Today’s Episode You Will Learn:

  • How did John make his way into the world of SaaS and more specifically customer success?
  • John has previously described customer success as ‘The Analogue of Sales’, what does he mean by this? How does it affect the way he views customer success
  • How does John view the role of sales vs customer success in large accounts? How do they partner to drive expansion?
  • How customer success managers be truly productive at the enterprise level? How can they measure their success with this productivity increase?
  • Moving downstream, why does John believe the $2m benchmark per CSM is the hardest phase? What skills do you need to be successful at this stage? With so many accounts, is it possible to be proactive?

60 Second SaaStr

  1. The biggest mistake most companies make when it comes to customer success?
  2. Most common questions asked by CSM leaders?
  3. Measuring customer success?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

John Gleeson

Lawrence Coburn is the Founder & CEO @ DoubleDutch, the category leader for event marketing automation. If you are at SaaStr and have the pleasure of using the SaaStr app, yep that is DoubleDutch! They have raised more than $75m in VC funding from some of the best VCs in the world including Index Ventures, Bessemer, Floodgate and Bullpen. As for Lawrence he is a three time entrepreneur, Lawrence also founded RateItAll, a top ten consumer review property, and LocationMeme, a blog about location based services. Lawrence is also the geo-location editor for The Next Web, is a mentor at IO Ventures, a San Francisco based incubator, and on the advisory board for the Enterprise 2.0 conference.

In Today’s Episode You Will Learn:

  • How did Lawrence made his way into SaaS and then came to found DoubleDutch, the category leader for mobile social events?
  • How does Lawrence look to use SDR as a growth engine and does he think it is important to invest in this early to build the machine?
  • How has Lawrence found the transition in terms of moving upmarket from SMB to Enterprise? How does Lawrence look to differentiate himself in such a crowded market?
  • How has Lawrence seen the evolution of the team? Does he agree there are different people for different phases of the growth cycle?
  • How does Lawrence look to use customer success as a bridge to cover gaps in product?

60 Second SaaStr

  1. Fave SaaS resource?
  2. What does Lawrence know now that he wish he had known at the beginning?
  3. What is the biggest challenge Lawrence faces to this day?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Lawrence Coburn

Michael Cardamone is the Managing Director of Acceleprise, a SaaS focused accelerator based in San Francisco and backed by leading operators. He is also an advisor to and angel investor in early stage SaaS companies. Prior to Acceleprise, Michael was one of the first 30 employees at Box in a business development role and then led partnerships at an EdTech company called AcademixDirect.  

In Today’s Episode You Will Learn:

  • How did Michael make his way into the world of SaaS and then start Acceleprise in SF?
  • How can founders know when is the right time to ship product? Does Michael agree with Reid Hoffman, ‘if you are not embarrassed by your V1, it is too late’? How should startups look to establish a pricing mechanism at such an early stage?
  • What are Mike’s thoughts on freemium? Before Mike has said founders can charge more than they think. Why does he think this and how can founders know when they have reached their price ceiling?

  • Do founders need to sell their own product? How should founders approach the sales learning process? What questions should they be asking
  • How important is it for a startup to have an ideal customer profile? Should founders be looking for influential customers early or just getting as many dollars in as possible? How impactful can big brands and companies be as customers to early stage companies?

60 Second SaaStr

  1. Scrappiness: good or not as it just simply isn’t scalable?
  2. Most common challenge for Mike’s companies?
  3. Fave SaaS reading material?
  4. Entrepreneur optimism: Let it run or be wary?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Michael Cardamone

 

Eoghan McCabe is CEO and co-founder of Intercom. The customer communications platform that has taken the saas world by storm in the last few years with 116m in VC funding from truly some of the world’s best including Bessemer, Social Capital and Index Ventures. He previously founded Contrast, an award-winning software design consultancy, and co-founded Exceptional, a developer tool startup acquired in 2011 and now a part of Rackspace.

In Today’s Episode You Will Learn:

  • How did Intercom break out in the early days with seemingly lots of competition and an install before you buy process?
  • In terms of category creation, in the early days how did Eoghan convince people of a product that had previously never existed? At what stage did Eoghan and Des stop selling the product themselves? When is the right time to hire your VP of Sales?
  • How did Eoghan establish a pricing mechanism for Intercom? Why is Eoghan such an advocate for value based pricing?
  • Why it is so important for founders and sales teams to have empathy for the customer? How can you practice empathy? How can you cheat empathy?
  • How does Eoghan manage a distributed workforce so well? What does he do to create links and culture between both the Dublin and SF office?

60 Second SaaStr

  1. Biggest advice to SaaS founders?
  2. Fave SaaS reading material?
  3. Most proud moment of Intercom’s journey?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Eoghan McCabe

Louis Jonckheere is the Co-Founder & Co-CEO @ Showpad, the company that enables sales teams by making content, findable, presentable and trackable. They have raised from some incredible investors including Dawn Capital, Hummingbird Ventures and Insight Venture Partners who more recently led their Series C $50m fundraise earlier this year. As for Louis, Showpad is his second company. He and his co-founder, Pieterjan, founded the mobile development agency, In The Pocket in 2010, where Louis still serves on the board. Prior to In The Pocket, Louis was a Strategic Partnership Manager at Netlog, where he first met Pieterjan.

In Today’s Episode You Will Learn:

  • How did Louis come to found Showpad? What was the a-ha moment for him?
  • How did Louis look to build out the core executive team? What have been the big lessons learnt? What have been the big mistakes and how has Louis changed his approach since?
  • How did Louis look to scale the customer success team? At what stage did Louis hire his first CSM? Is $2m ARR the right benchmark? Do customer success teams need to be product specialists?

  • How has Louis looked to build a scalable and repeatable sales process with Showpad? At what point did Louis decide to hire sales reps for the first time? What benchmark was this? Did Louis hire the first 2 reps at the same time?

60 Second SaaStr

  1. Louis’ Fave SaaS resource?
  2. Louis’s biggest advice to SaaS founders?
  3. What does Louis know today that he wishes he had known at the start?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Louis Jonckheere

Tim Kopp, Tim is a Managing Partner with Hyde Park Venture Partners one of the leading early stage VCs in the Midwest. Prior to joining Hyde Park Venture Partners, Tim was the CMO of ExactTarget for 6+ years, leading a global team of nearly 300 amazing marketing leaders. Tim helped grow ExactTarget from $47M to $400M in revenue, through IPO, and ultimately to a $2.7B sale to Salesforce. He previously spent 10+ years in consumer marketing with P&G and Coca-Cola. You can follow his advice for startup executives and marketing leaders at his newly launched website:www.cmovc.com.

In Today’s Episode You Will Learn:

  • How Tim made his way into the world of B2B marketing and then made the transition into the world of venture?
  • Why does Tim believe marketing in B2B is unbuilt and uninspired? What would Tim like to see change?
  • What are SaaS CEO’s doing wrong with regards to organisation and scaling of their marketing team? What questions should they be asking?
  • Why does the best B2B marketers come from the world of B2C? What makes them more effective than current B2B marketers?
  • Why is ABM the most revolutionary thing to happen to marketing for the last decade? How can startups and CEOs integrate ABM into their current marketing forecasts?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Tim Kopp

Jim Stoneham is VP of Infrastructure Products @ New Relic and Jim joined New Relic when the company acquired Opsmatic, where he was co-founder and CEO. Prior to Opsmatic, Jim was CEO of Payvment, a social commerce platform for SMB sellers that was acquired by Intuit in early 2013. He joined Payvment from Yahoo, where he led Communities (Flickr, Answers, Groups, Delicious) as well as the integrations of Facebook and Twitter into Yahoo products. Prior to that, he spent several years building consumer products at Kodak and Apple. A huge thanks to Cindy Padnos @ Illuminate for making the introduction, without which this interview could not have happened.

In Today’s Episode You Will Learn:

  • How Jim came to found Opsmatic and why he decided to sell to New Relic over other acquirers?
  • Why does Jim have a preference toward hiring senior experienced individuals over young talent to the founding team?
  • At what stage should startups look to bring on fresh, inexperienced candidates who are passionate for the job but in need of mentoring and guidance?
  • Question From Cindy Padnos: John is a master of employee onboarding, so how does John look to onboard new employees in the most effective and fast manner?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Jim Stoneham

Chad Arimura is the Founder & CEO @ Iron.io, where he drives the team to build the world's best cloud infrastructure services. Now they do have some pretty sizeable clients including the likes of Google, Zenefits, Twitter, Whole Foods and they have the backing from the likes of Steve Anderson’s Baseline Ventures, Bain Capital, Matt Ocko from Data Collective and our friends at Sapphire Ventures just to name a few and Prior to co-founding Iron.io, Chad was CIO and founder of AllDorm Inc., a collegiate media and marketing company that provided fundraisers and viral marketing campaigns for clients such as Volkswagen, Domino's Pizza, and Visa.

In Today’s Episode You Will Learn:

  • How Chad came to found Iron.io ?
  • With a complex product like Iron, how much of a role does education play in the onboarding process for prospective new clients?
  • To what extent does content marketing play the dominant marketing function for Iron both in terms of educating customers and converting potential customers?
  • How does Chad view the balance of much larger ACV clients with long sales cycles compared to SME’s with smaller ticket sizes and shorter sales cycles?
  • What are the challenges when selling to large corporates and CIO’s in the traditional corporates?

60 Second SaaStr

  1. What does Chad know now that he wish he had known at the beginning?
  2. What is Chad’s favourite reading material?
  3. How does Chad deal with stress as a Founder & CEO?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Chad Arimura

Greg Sands is the Founder and Managing Partner of Costanoa Venture Capital. Prior to founding Costanoa Venture Capital, Greg was a Managing Director at Sutter Hill, where he was an early investor in the likes of Feedburner, AllBusiness, and Return Path just to name a few. Before Sutter Hill, Greg was the first hire at Netscape after its founding engineering team. As Netscape’s 1st Product Manager, Greg wrote the initial business plan, coined the name Netscape, and created the SuiteSpot Business Unit, which he grew from zero to $150m in revenue. He also served as Manager of Business Development at Cisco where he architected a global channel management plan.  

In Today’s Episode You Will Learn:

  • How Greg made his way into the world of VC from Netscape?
  • Why did Greg see the opportunity for an early stage B2B fund like Costanoa? Why did this fund not exist in B2B but was becoming popularised in B2C?
  • To what extent does Greg agree SaaS investing is ‘traction capital’? When investing pre metrics, what are the signs of promise Greg looks for?
  • How does Greg assess product market fit? Why is customer segmentation and customer archetypes so important?
  • What does Greg make of the ‘full stack CEO’? Is it better to be specialised or jack of all trades? When is the right time to specialise?

60 Second SaaStr

  1. Greenfield opportunity in SaaS?
  2. Biggest advice to startup founders in SaaS?
  3. Easier or harder to raise money now than before?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Greg Sands

Jon Herstein is the Senior Vice President of Customer Success at Box where Jon works to ensure that all of Box's Enterprise and Business customers are phenomenally successful. Jon has worked with some of the biggest names in the tech world, including Accenture, Informatica and most recently NetSuite, where he served as VP of Professional Services for North America and EMEA. Before NetSuite, Jon led the turnaround of Informatica's European consulting practice during a multi-year expatriate assignment, which eventually led to a 65% jump in revenue.

In Today’s Episode You Will Learn:

  • How Jon made his way into the newly created category of customer success?
  • How does Box define customer success and how does that impact their view and approach to the SaaS industry?
  • Box has gone through the definition of private hypergrowth and is now in the next phase as a public company - how has that affected the CSM strategy?
  • Box now have some very large accounts, how do you distinguish between the role of sales vs CS in large accounts? How do they partner to drive expansion?
  • Jon is renowned for prioritizing career paths for his team, how does he accomplish this and balance this with wider operational and strategic goals of box?

60 Second SaaStr:

  1. What's the most common question Jon hears from CSM leaders?
  2. What's one innovative idea Jon has tested that might be shared with the audience, vis-a-vis Customer Success?
  3. What do you know now that you wish you had know when you started?
  4. The biggest mistake current saas companies are enacting with their CS process?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Jon Herstein

Kristen Koh Goldstein is the Co-Founder @ HireAthena, the on demand workforce specialising in accounting, HR and payroll. Prior to Hire Athena, Kristen was the Co-Founder @ Scalus, where she raised millions of dollars in venture capital from top VCs including Google Ventures and Sherpa Capital. Before that Kristen was the Co-Founder @ BackOps, the world’s fastest growing back office solution. If you enjoy the show with Kristen today and would like to join Jason and I @ SaaStr Annual 2017 next year, then all you have to do is checkout SaaStr and buy your tickets for SaaStr Annual 2017.

In Today’s Episode Kristin Discusses:

  • Why it is that the faster you hire, the longer it takes to build your business? How to make the transition from a family to a village with your team?
  • Why it is imperative to hire slowly and fire fast? How to communicate new hires to the existing team to ease onboarding friction?
  • Why hiring outside of your circle is full of risks? What you can do to mitigate those risks?
  • What happens when you wake up one day and realise you are the problem in your own business?
  • What really is scaling with regards to the product? How important is product consistency in the scaling process?

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

Matthew Bellows is the Founder @ Yesware and a specialist in helping sales people close more deals faster. Yesware serves more than 750,000 salespeople at companies like IBM, Groupon, Salesforce, Twilio, Yelp, VMWare, and Zendesk. Prior to Yesware, Matthew was the VP of Sales at Vivox. Before that, he was GM at Floodgate (acquired by Zynga) and Founder/CEO of WGR Media (acquired by CNET Networks).

In Today’s Episode with Matthew We Discuss:

  • How Matthew came to be Founder and CEO @ Yesware? What was the a-ha moment for him?
  • Whether sales is an art or a science and what makes Matthew feel this way?
  • Why all founders should do sales until $1m ARR? What were Matt’s personal learnings from scaling the sales team with Yesware?
  • Why a CEO cannot also be a VP of Sales? When is the right time to hire an exec to run the sales team and begin sales specialisation?
  • How Matthew approaches the hiring process? What is the best way to receive high quality candidates? What does his interview process look like?
  • With the array of data on sales activity how can managers balance management with micro-management? What are the inherent problems?

60 Second SaaStr:

  1. If Matthew could do the process again, what would he redo?
  2. How does Matthew deal with rejection in business and sales?
  3. Strategies to optimise email open rates?

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

Ryan Fyfe is the Founder & CEO @ Humanity, the employee scheduling software that allows you to value your employees. Ryan has built Humanity to serve more than half a million users across 87 countries, with a team exceeding 100 people and continually growing across 3 continents. They have raised funding from our friends at Point Nine and a huge thank you to Christoph @ Point Nine for making the introduction today.

In Today’s Episode with Ryan We Discuss:

 

  • How did Ryan come to be founder and CEO at Humainty?
  • How does Ryan and Humanity use data to affect the marketing decisions they make with regards to customer acquisition?
  • How does Ryan look to integrate customer success into the pre-purchase period to facilitate adoption?
  • How does Ryan view free trials with Humanity? How do they A/B test free trials to optimise for conversion?
  • How can startups ensure efficient time to value in a trial period and what is the role of customer success in this?

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

Michael Litt is the Founder & CEO @ Vidyard the video intelligence platform that allows you to create, measure and strengthen engagement of your video content. Vidyard are based in Canada and have raised over $60m in VC funding from the likes of Battery Ventures, Bessemer, SoftTech, Salesforce Ventures, some incredible names there and the list goes on but I would like to say a  huge thanks to Matt Garrett @ Salesforce Ventures for making the intro.

In Today's Show with Michael We Discuss

 

  • How did Michael come to found Vidyard, as Paul Graham described, ‘The Google For Business’?
  • How does Michael assess value based pricing and how has his views transition with the growth of Vidyard?
  • What does Vidyard’s internal sales organisation look like? How does Michael look to optimise this structure?
  • How does Michael view the utility of the freemium model? What are the inherent advantages and disadvantages that need to be considered?

In a round we call the 60 Second Saastr, we also hear:

  1. Productivity tips and tricks?
  2. Cool hobbies, what are they?
  3. Fave SaaS material?

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

Today’s episode is taken from SaaStr Annual 2016, featuring Meagen Eisenberg, CMO at MongoDB and former VP Demand Gen at DocuSign, sharing her playbook for optimizing the funnel at every stage and converting leads into real, paying customers. If you want to join me and Jason @ SaaStr 2017 then head to saastr.com where you can buy tickets.

In Today’s Episode You Will Learn:

 

  • Why you need to think about more than just pipeline? What are the other elements of the funnel you should focus on?
  • How to optimise your forms for data capture to allow your sales team to follow up successfully?
  • How marketing can provide support to sales to attract new customers?
  • How does nurturing align the buyer with your sales team?
  • How do you accurately measure success within email marketing?
  • How can startups on a tight budget maximise exposure through content and social media?

 

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

Aaron Ross is the author of the best selling book, Predictable Revenue, providing the framework for the outbound process & sales team Aaron created for Salesforce.com. During his time at Salesforce as Director of Corporate Development and Acquisitions, he added an extra $100 million in revenue in just a few years. In today’s show we discuss his and Jason Lemkin’s fantastic new book, From Impossible To Inevitable, which outlines how hyper growth companies create predictable revenue? If you are a founder asking why aren’t we growing faster, how do we go into hyper-growth mode and then how do you sustain growth then this book really is for you.

In Today’s Episode with Aaron You Will Learn:

  1. How did Aaron enter the world of SaaS and come to be a Senior Director @ Salesforce? What were his biggest takeaways from seeing Salesforce scale into hypergrowth mode?
  2. WHat does Aaron mean by saying ‘nail a niche’? Does this mean go small? How much of a role does iteration play in this process?
  3. How does Aaron assess product market fit? How do you really know when you have that focus? Are there any clear signs that suggest you have achieved product market fit?

  4. Aaron has said before “people at the company will always be busy. they just might not be busy on the right things”? How important is sales specialisation? At what point does the original generalist sales team fragment into specialised elements?
  5. What are Aaron’s thoughts on ownership and how you ensure that a sense of ownership is instilled upon the team to enhance productivity? I have never heard a Founder on the show before saying ‘my team is just achieving too much!’.

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

As VP of Sales and Marketing at Atlassian for three years before becoming President, Jay Simons has a broad perspective on what it takes to build a successful company. Sometimes, ignoring conventional wisdom is what will differentiate you from the competition. Bootstrapping from day one, launching and supporting multiple products, and doing it all without traditional Sales team - Atlassian's approach (and wild success) has always been a curious anomaly in SaaS. After 13 years of being an exception to every rule, Atlassian went public in late 2015 with a total market capitalization of $4.37B at the time of the IPO.

In this session, Jay answers our burning questions: 

1.) Why does Jay believe in most cases the best run companies are public companies? What does being public bring to the organizational structure of a firm?

2.) How important is it for early stage startups to have board members and outside perspectives? How should they select those inputs?

3.) How important a role does customer support and success play in the conversion of customers from trial to paid versions?

 4.) How does Jay focus on 4 products with such a differentiated suite of products? Does this not contradict the often cited fundamental, focus.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin
Harry Stebbings
SaaStr

Andy Sparks is the Co-Founder and Head of Sales @ Mattermark. He was previously the Technology Editor at Referly before the company pivoted to become Mattermark. Andy joined the Referly team via an acqui-hire of his company, LaunchGram, by Referly in February of 2013. Now I am going to leave the bio there as Andy does a much better job of it in the show than I do!

In Today’s Episode You Will Learn:

  • How Andy came to be a 1st time Head of Sales with Mattermark?
  • What are the requirements for stretch VPs to be successful?
  • How can Head of Sales clearly and efficiently communicate with their reps? What are the 3 things all sales reps have to be trained on?
  • What are the must haves when looking at sales reps? Are there different types of reps for different stages in the business?
  • How to effectively establish a compensation structure for your sales team that is incentivising to them and to the company?

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

 

Today we bring you one of the highlights from SaaStr Annual 2016 with Jason Lemkin talking to Kirsten Helvey,  COO of Cornerstone Ondemand, a cloud-based learning and talent management solutions provider. in the episode Kirsten discusses her 11 years of experience with rising up in the ranks from employee #30 to her current position in the company, which is now 1500-strong, it is a phenomenal scaling story and so many insights nuggets of wisdom from Kirsten here.

In Today’s Episode You Will Learn:

Why you should always be thinking about building, no matter the scale?

Why we should all stop talking about company culture?

Why you should forget the MBA and take a psychology degree?

How to give direct and consistent feedback with employees in order to get the most out of them?

Why we should focus more on upsell and less on customer acquisition?

How to build, integrate and scale a customer success team into a 1,500 person organisation?

You can follow us on Twitter here:

David Yuan is a General Partner at Technology Crossover Ventures, where he has enjoyed no less than 4 IPOs and 5 acquisitions. Some of David’s investments include the likes of Facebook, Linkedin, Exact Target (acq by Salesforce), Splunk and many more incredible companies. He also sits on the board at Act On, App Nexus, Merkle and Site Minder and is an advisor to Pinterest. Pior to TCV, David had stints at JP Morgan and Bain & Company.

In Today’s Episode with David You Will Learn:

  1. How did David make his way into the investing world in 2000?
  2. How has David seen the evolution of SaaS revenue multiples over the last decade?
  3. How can VCs balance the drive for profitability with their need for big wins over a short 5-7 year investment cycle?
  4. How does David approach investing cadence in correlation to market cycles? Does his strategy alter according to down-turns and booms?
  5. Why does David find the monetisation models of the consumerisation of SaaS to be the most exciting?
  6. Does David agree that the original hires might not be the hires as the stages progress? How can founders transition them out without a lack of respect and gratitude?

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

Today we bring you a highlight from SaaStr Annual 2016 featuring a conversation between Hubspot's Dharmesh Shah and SaaStr's own Jason Lemkin. Prior to founding HubSpot in 2006, Dharmesh was founder and CEO of Pyramid Digital Solutions, which was acquired by SunGard Data Systems in 2005. In addition to co-authoring “Inbound Marketing: Get Found Using Google, Social Media and Blogs”,Dharmesh published HubSpot’s Culture Code, which has garnered over 2.5 million views on SlideShare. Named an Inc. Founders 40 in 2016, he is an active member of the Boston-area entrepreneurial community, an angel investor in over 60 startups, and a frequent speaker on startups and inbound marketing.

In Today's Episode wth Dharmesh You Will Learn:

  • What were the biggest growth catalysts in the scaling of Hubspot from Day 1 to IPO?
  • What were the biggest mistakes made and lessons learnt by Dharmesh and the team throughout the journey?
  • How does Dharmesh think about churn? How does he define pre-churn?
  • What is the customer happiness index and how can it be implemented?
  • How can founders inform prospects their product is a must have not a nice to have?
  • Why has the SMB space been so difficult for so long? Why is that changing now?
  • Why Dharmesh and Hubspot focus on consumer behaviour not consumer feedback?

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

Allison Pickens carries the customer success torch as the VP of Customer Success & Business Operations at the category leaders, Gainsight. Allison’s organization @ Gainsight includes all post-sales functions: CSMs, Support, Onboarding, Services, and Operations. Prior to Gainsight, she started her career in management consulting for Fortune 500 companies while at Boston Consulting Group and later worked in private equity investing at Bain Capital.  Allison decided that she couldn’t pass up the opportunity to work at Gainsight when Bain Capital led the Series B.

In Today’s Episode With Allison You Will Learn:

1.) So let’s start with managing customer churn and I think the first and most important thing is assessing what is regrettable vs non-regrettable. How do you approach this?

  • What is the internal post mortem?
  • How do you identify why they churned?
  • Is there a blame game that follows? How do you instill ramifications but not fear?
  • How do you then look to fix the original problem that caused the churn?

2.) To do the above we need to have a great customer success team so iw ant to talk about the process of building this out and with CS being a new category this is an aspect a lot of founders are addressing at this time. So starting with the obvious?

  • When do you need a customer success team?
  • Where in the organization should the team sit?
  • What's the playbook for rolling it out?
  • How big does the team need to be? Does this vary on sector or funding availability?
  • What are the levels of seniority within the team?
  • What's your budget? How do you account for the costs of your team?
  • What teams sit within the customer success umbrella?

60 Second Saastr produced by Nick Mehta:

What surprises you most about customer success now vs a year ago?

Importance of fast iterating team?

Fave SaaS material, book, blog, podcast?

What element of the journey have you found most challenging?

Carrying the CS torch? What is it like do you feel the pressure?

3.) Now I want to finish today by discussing the segmentation of your customer base, so at what point in the company's life do you begin segmenting the customers?

  • Why is it important to segment customers?
  • How do you decide the best way to segment them?
  • Should these segments align with the sales team?

 

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

Cindy Padnos is the Founder and Managing Partner at Illuminate Ventures where she focuses on all things Enterprise/B2B cloud and mobile computing sectors. Prior to founding Illuminate in 2009, she was one of three investment professionals at Outlook Ventures responsible for committing the firm’s $140 million fund. Cindy also has extensive experience in the world of operations, where she founded and sold one of SaaS’ first on demand startups in the form of Vivant.

In Today’s Episode with Cindy We Discuss:

  • How Cindy made her way into the world of SaaS and later SaaS investing?
  • Why does Cindy think SaaS is a democratiser for entrepreneurship?
  • Is the proliferation of Sales and Marketing tools not a challenge for startups in terms of competing for the same VC dollars?
  • Is it easier or more challenging for startups to raise VC funding today than in previous years? If so, why?
  • How does Cindy assess product market fit with her portfolio companies? When is the right time to put pedal to the metal?
  • What does Cindy make of the Micro VC market at the moment? How prominent are party rounds? Will we see consolidation?

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

Fred Stevens-Smith is the Co-Founder & CEO @ Rainforest QA, which if you listened to 20VC with Byron Deeter, you will remember he discussed them and their amazing trajectory. So for QA first, it is essentially QA as a service making it fast and easy to test your webapp in multiple browsers and they are backed by some of the best as we said there Byron Deeter @ Bessemer, our own Jason Lemkin, Y Combinator, previous guest Kris Duggan @ Betterworks and Marc Benioff just to name a few. As for Fred he is the man at the helm as Co-Founder & CEO and absolutely smashing it I might add. In the show Fred mentions his favourite reading material to be Jason Lemkin and Aaron Ross’s new book From Impossible to Inevitable: How Hypergrowth Companies Create Predictable Revenue and if you have not read that, that is a must and can be found here!

In Our Discussion with Fred You Will Learn:

  • How did Fred come to found Rainforest QA? What was his origin story to YC?
  • How did Fred look to establish the pricing model with Rainforest? Why does Fred believe most software companies undervalue their software?
  • What are the challenges of going upstream? How does it affect product? Sales cycle?
  • Does Fred agree with Mark Organ that in a new category, the company CEO must be the category CMO? How much of a role does content play in Rainforest QA’s education funnel for customers?
  • Why does Fred believe you should spend the most time with your best people? Similarly, the least amount of time with your worst people?
  • How has Fred gone about building out the sales team? What did Fred look for in sales reps and Heads of Sales?

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

Quang Hoang is the Co- Founder @ Birdly, Birdly are convinced by the power of messaging within organizations, they decided to build a broader service that connects your favorite business softwares to messaging apps. It is this vision that has led to them being named one of the hottest startups from YC Winter 2016 batch and has led to funding from some of the best in the industry including our own Jason lemkin, Slack, previous guest Nicolas Dessaigne and prestigious french investors Alven Capital and Partech Ventures.

In Today’s Episode with Quang We Discuss:

  • How did Quang come to found Birdly? What was the a-ha moment?
  • What did Quang learn from pivoting to Birdly? What is it important for founders to consider before a pivot?
  • How does Quang approach the challenging topic of a business model for bots?
  • Why does Quang believe that the whole pricing model for SaaS will change?
  • What were the main benefits of the YC experience and how did it impact his fundraising?
  • When is the right time for European startups to make the move to SF? How important is it to be close to your customers?

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

Christoph Janz is the Co-Founder and the Managing Partner @ Point Nine Capital, one of Europe’s best early stage venture funds and Christoph himself specializes in all things SaaS at Point Nine and has made more than 20 SaaS startup investments. Prior to Point Nine, Christoph co-founded two Internet startups and in 2008, became an angel investor and discovered Zendesk, which was his first angel investment. Also if you would like to congratulate Jason for the raising of the incredible new SaaStr Fund then you can click here to send him a congratulations tweet.

In Today’s Episode with Christoph We Discuss:

  • How did Christoph make his way into the world of early stage SaaS investing?
  • When should startups consider making the move to the US? Is it always necessary?
  • How important is it for SaaS startups to have a local US investor? What are the benefits?
  • Where are there talent gaps in European SaaS? What can European founders do to find those experienced VPs of Sales and Marketing?
  • Question from Jason: What made Zendesk seem like such a winner and what did that teach you?
  • Where does Christoph see the next wave of the consumerisation of SaaS?
  • Is it harder to get funded as a SaaS startup in today’s environment than in previous years?

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

Matt Garratt currently runs Salesforce Ventures with the mandate to build out salesforce’s ecosystem of partners with equity investments. Matt has led key strategic investments at Salesforce in companies such as former guests Gainsight, and Invoca as well as Anaplan and Insidesales.com just to name a few. Prior to salesforce Matt was a VP at the prestigious SaaS investor Battery Ventures. Also in the show today we mention Jason Lemkin and Aaron Ross new book From Impossible to Inevitable: How Hypergrowth Companies Create Predictable Revenue and if you have not read that, that is a must and can be found here!

In This Episode With Matt You Will Learn:

  • How Matt made his entry into the world of VC and came to run Salesforce Ventures?
  • What did Salesforce do right to give Matt the ability to formalise the fund? What did Matt learn in the less formal stages of investing?
  • What are the benefits that startups receive from being portfolio companies of Salesforce Ventures?
  • How does matt view Salesforce Ventures in the early stage investing landscape? Does Matt like to co-invest with other prominent funds?
  • How does M&A work within Salesforce Ventures? Are you willing to sell to your competitors?

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

I am delighted to welcome the new Head of Sales @ Front App, Cailen D’sa, to The Official SaaStr Podcast today. Cailen might just be the Head of Sales every SaaS startup founder is dreaming of having previously been the first sales hire @ Dropbox where he launched Dropbox’s first B2B product, prior to that he was a director at Box where he helped pioneer and operationalize the freemium land-and-expand sales model, which is now a core SaaS sales methodology. Now if you enjoy the episode with Cailen today and want to hear more from him then you must headover to Front’s blog where you can find Mathilde’s written interview with Cailen.

In This Episode With Cailen You Will Learn:

  • How did Cailen come to be the first Sales hire @ Dropbox? What was it about Front that enticed him?
  • What were Cailen’s biggest takeaways from his time at Dropbox and Box?
  • How does the Sales process differ when selling a freemium product like Dropbox, compared to an enterprise product like Front?
  • What does Cailen look for when hiring sales reps? What are Cailen’s sourcing strategies for new sales reps? How does Cailen incentivise the best talent to choose Front over other options?
  • With the rise of data and it’s role in sales, to what extent does Cailen still believe sales to be an art and not a science?

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

Villi Iltchev is a Partner @ August Capital and prior to joining August Villi was a member of the leadership teams at Box and Lifelock. Before that Villi was a Vice President @ Salesforce where he led the strategy and acquisitions teams; being directly responsible for over 30 investments in the likes of Hubspot, Box, Mulesoft and many more amazing companies.

In Today’s Show with Villi We Discuss:

  • How Villi made the transition from the world of operations to investing with August?
  • What were Villi’s biggest takeaways from working with titans of SaaS; Box, Salesforce?

  • What was the M&A environment like back in the 2000s? What was the driver behind mass consolidation? What did the on premise perpetual license business model enable companies? Where did customer success lie in this environment?
  • Multiple Clouds: What is the challenges of this? How will this evolve over time? What are the current solutions?
  • Customer success lies with the vendor: What do you think caused this pivotal transition? How central should customer success be to an early stage SaaS company’s strategy? What are the main benefits of customer success to you?
  • SaaS distribution: Why do reseller arrangements not work? How would you like to see this evolve in the future?
  • Sales productivity: What is the productivity effect of giving another product to sales? What happens to aggregate sales?

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

Luke Kervin is the Co-Founder & Co-CEO @ PatientPop, where he has scaled the team from 10 to over 130 in just 12 months. As a result, PatientPop recently raised their Series A led by Toba Capital, allowing them to further ramp up their customer base and expand the employee ranks to over 200 people.

In Today’s Show with Luke We Discuss:

  • How Luke came to found his first SaaS business in PatientPop?
  • What is Luke’s criteria for selecting a potential business idea? What does the idea need to have? What elements of an idea will concern Luke?
  • How did Luke go about validating the idea for PatientPop? What are the most common methods founders get product validation wrong?
  • Why did Luke build a fake product, a fake website and fake business cards to validate the idea?
  • PatientPop has grown from 10 to 130, so how did they scale so fast? What are the inherent challenges of company culture maintenance with such hyper-growth. 

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

Blake Bartlett is a Partner @ Openview Ventures where he helps identify value and lead investments in product-led businesses driving market dislocation. Prior to joining OpenView, he was a Vice President at Battery Ventures, where he focused on growth-stage software and Internet businesses. Blake joined Battery in 2009 and helped lead 10 investments including  the likes of Wayfair, Optimizely, Sprinklr, and Glassdoor.

In Today’s Show We Discuss:

  • Why Blake decided to invest in SaaS over other sectors?
  • Whether the rise of the bottoms up SaaS sales model means customer fickleness for SaaS products will increase?
  • Does product led growth contradict tradition SaaS sales beliefs? How can they work in unison?
  • Is product market fit and customer value a binary result? Are there varying degrees of customer value? How important is time to customer value?
  • How can startups look to pull product-led growth off? What were Blake’s biggest takeaways from watching the likes of Optimizely and Expensify?

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

 

I am delighted to welcome my first ever Harry to the show today in the form of Harry Glaser, Co-Founder & CEO @ Periscope Data, the worlds fast analysis suite providing data analysts with the tools they need to improve their analysis by over 150X and an astonishing fact here they have doubled their revenue every 3 months ever since launch. Periscope’s investors include Ellen Pao, Matt Ocko @ Data Collective, Chad Byers @ Susa Ventures, Wes Chan @ Felicis, Benjamin Ling at Khosla and many more. Also in the show today we mention Jason Lemkin and Aaron Ross new book From Impossible to Inevitable: How Hypergrowth Companies Create Predictable Revenue and if you have not read that, that is a must and can be found here!

In Today’s Episode with Harry We Discuss

  • How Harry came to be the founder of Persicope Data and what the a-ha moment was for him?
  • How did Harry look to establish a pricing model with Periscope Data as a first time SaaS founder?
  • What are Harry’s learnings of hiring and building out the initial sales team?
  • How did Harry build out the institutonal training program to allow non technical people to sell a very non technical product?
  • What are the inherent pros of having an inbound heavy model and what are the fundamental problems?
  • Why are companies suddenly seeing the need for data analysts and what are the opportunites that data analysts present?

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

Andy Wilson is the Co-Founder and CEO @ Logikcull, where he really is the visionary behind Logikcull’s product and marketing strategy focusing on simplifying and democratizing the discovery process into three simple steps: upload > search > download. Andy leads the company it its mission to put an end to eDiscovery with the use of Discovery Automation.

In Today’s Episode with Andy We Discuss:

  • The origin story of Logikcull for Andy and what a-ha moment was for him?
  • How did Andy approach the transition from service based business to SaaS business?
  • Does the increase of customer success not transition the customer into the client?
  • What was the effect of having Jason as a investor and what are the biggest value adds that Jason provides?
  • On outbound vs inbound, how did Andy increase outbound in such an established space? Where did he find the major breakthroughs?

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

Super excited to welcome a heavy weight of the SaaS industry today as we have Mark Organ, Founder & CEO at Influitive. Influitive helps B2B companies mobilize their army of advocates for more rapid and profitable revenue growth. Prior to Influitive, Mark was the founding CEO of Eloqua, growing the business to over 150 people, hundreds of clients and a major presence around the world in 7 years. Eloqua was eventually bought by Oracle in 2012 for a reported $810m.

In Today’s Episode with Mark We Discuss:

  • The founding story behind Influitive? What was the a-ha moment behind the concept?
  • What were Mark’s biggest takeaways from watching Eloqua scale into the global force that it became?
  • Influitive are creating a category, so how is that for Mark? What are the inherent challenges?  What are the commonalities of successful category creators?
  • What is the difference between good and bad competition? Why does Mark try and encourage good competition?
  • Why are brand advocates crucial to the success of a business? Is it a really scalable solution? How did you figure out the model for making customers successful?  

In a round we call the 60 Second Saastr, we also hear:

  • Mark’s fave SaaS resource and reading material?

  • Thought leadership: Fundamental or unnecessary?

  • Target Markets; Go large or be specific and niche?

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

Laura Roeder is the Founder & CEO @ Edgar, the social media automation tool that essentially allows your social media queue to fill itself up. Now Edgar is not the usual startup story we are all familiar with as Edgar has taken some unusual steps, they have not raised VC funding, they do not have a sales team, their founder, Laura, was pregnant on launch and after all this, Edgar is a startup that actually makes money at 2.9m ARR.

In Today’s Episode with Laura We Reveal:

  • How did Laura come to found Edgar? What was the a-ha moment for Laura?
  • How did Laura assemble and build the team, with te restraint of being pregnant during launch? How did this hiring mindset benefit the process?
  • Why does Laura deliberately not have a sales team?
  • How does the SaaS math differ for bootstrapped vs venture funded SaaS startups? HOw does the exit strategy change when bootstrapped?
  • Why should SMs approach social media platforms one at a time? How can startups measure their social media performance and engagement?

In a round we call the 60 Second Saastr, we also hear:

  • Fave SaaS resource and reading material?
  • Hardest hire in the Edgar process?
  • Going up the enterprise funnel: Potential or not going to happen?

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

 

Bill Binch is a leader and expert in the SaaS sales industry. Bill was the senior vice president of worldwide sales at marketo for 8 years and he joined when it was a small venture backed startup with a mission to reinvent marketing automation, it was his sales leadership and expertise that formed a critical component in building Marketo into one of the fastest growing enterprise software companies in the world. Recognized through his being awarded worldwide VP of sales in 2011.

In today's show with Bill we discuss:

  • What were Bill’s biggest takeaways from his time scaling the sales organisation at Marketo??
  • Why did Bill find it enticing selling to sales and marketers with Marketo?
  • How can startups go about approaching the topic of the sales cycle? What does the right cadence look like?
  • How can sales leaders look to establish a quota that is achievable and confident? Why is it about deal frequency not dollar size?
  • How can we optimise the hiring process for sales professionals? What are the benefits to over hiring? Is this sustainable in a downturn?
  • Does Bill agree that customer success will be the new sales, as Nick Mehta stated?

In a round we call the 60 Second Saastr, we also hear:

  • SaaS tools that Bill could not live without?
  • Creating your own scorecard?
  • What does Bill know now that he wished he had known at the beggining

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

I am delighted to present Part 2 of our feature of Gainsight. Joining me today I have Anthony Kennada, the founding VP Marketing at Gainsight where he is responsible for managing the company’s global marketing strategy, from demand generation to brand marketing, and is credited with creating the “Pulse” community of Customer Success leaders. Anthony began his career as an early employee at Box. He later joined LiveOffice and managed their OEM partnership with Symantec from contract signature to acquisition for $115M. Prior to joining Gainsight, Anthony led the Emerging Cloud Products division at Symantec, and was responsible for the first organic product development effort that spanned both consumer and enterprise market segments.

In today's show with Anthony we discuss:

  • How Anthony came to be VP of Marketing at one of the hottest startups in the valley?
  • Being the founding VP of Marketing, how did Anthony look to grow the team? What were the actual steps Anthony used to scale the marketing at Gainsight?

  • How has B2B marketing changed, from Box to today? With this evolution, what are Anthony’s marketing learnings in creating new categories vs. new players in existing categories?

  • How should we be thinking about marketing, both Demand Gen and Corporate, differently in crowded spaces? ?

  • How can marketing help support going up market and driving ACVs up?  Both Box and Gainsight did this.

  • How should CEOs and VPMs think about, and budget events?  What if they don't have all the capital Gainsight does?

In a round we call the 60 Second Saastr, we also hear:

  1. Billboards: Stupid or effective?
  2. Fave SaaS resource and why?
  3. 3 Biggest Tips For Running a Successful Event?

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

This week on SaaStr we are celebrating the rise of GainSight with a special feature week dedicated to Gainsight and joining me today we have Gainsight CEO, Nick Mehta. Since Nick has been at the helm of Gainsight, it has experienced a meteoric rise to the top of the world of SaaS having practically created the category of customer success and revolutionising business work processes in doing so. Due to this, Gainsight has raised funding from the likes of Battery Ventures, Lightspeed Venture Partners and Bessemer Venture Partners.

In today's show with Nick we discuss:

  • What were the solutions before Gainsight? Why were these inefficient and what the market opportunity for Gainsight?
  • Why has the power shifted from the hands of the vendor to the hands of the customer? What can vendors to do optimise this shift?
  • Is the proliferation of available tools and the resulting competition not dangerous as there is only so low prices can go?
  • To what extent does Gainsight have a monopoly over the customer success market?
  • How much should startups spend on customer success in the early days? How can one measure that success and return on investment?
  • What does the hiring of a customer success officer look like for Nick? How can we optimise this process?

In a round we call the 60 Second Saastr, we also hear:

  • ACV is everything: Explain?
  • Being a specialised CEO: Right or wrong?
  • On again, off again hiring in sales?

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

Joining us today on The Official Saastr Podcast is Nakul Mandan, Partner @ Lightspeed Venture Partners, where he focuses on early stage SaaS investments. At Lightspeed, Nakul led the firm’s investments in Gainsight and Reflektive. Previously, Nakul worked at Battery Ventures, where he helped lead the firm’s investments in category defining companies such as Marketo, BlueJeans Networks, Gainsight, Intacct, 6Sense and Yesware. Prior to Battery, Nakul worked at Blue River Capital, a growth stage investor focused on India.

In today's show with Nakul we discuss:

  • How Nakul came to be one of the leading SaaS investors in the US?
  • What will the 2nd phase of the consumerization of the enterprise entail? What innovation will we see in business model?
  • How important is predictable revenue for early stage startups? Hoe can they mitigate the circumstances of losing it?
  • What more needs to be done to ensure the continuation of consumerising traditional enterprise software?
  • What does Nakul hone in on when considering investing in a SaaS startup for Series A? What are the metrics and requirements that matter? At this stage are there large data sets and metrics to rely on?

In a round we call the 60 Second Saastr, we also hear:

  • Fave SaaS reading material?
  • Greenfield Opportunities in SaaS?
  • SaaS Founder Nakul most respects and admires?

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

I am so excited to welcome Russ Hearl, Head of Sales @ Datahug. Datahug is a pipeline management and forecasting solution within Salesforce and backed by the likes of DFJ and Salesforce Ventures. Prior to Datahug, Russ was the VP of Sales at DoubleDutch where he built a sales machine that delivered over 1,500 new customer wins and took the business from $0 to over $20 million ARR in less than three years.  A true thought leader in sales optimization and selling velocity.

In Today’s Episode You Will Discover:


  • What makes a great SaaS sales leader? How can you spot the BS and the façade of someone who does not have what it takes?

  • How do the best leaders run 1 on 1’s with their reps? How can leaders optimise this time and interaction? Is there anything they should avoid in the process? ?
  • How can sales leaders go about introducing elements of competition into sales without disincentivising the loser? What is the buddy system and how does that work?

  • Why do SaaS founders need to make pipeline velocity optimization a priority today? What are the biggest opportunities in improving pipeline velocity?

In a round we call the 60 Second Saastr, we also hear:

  1. Biggest opportunities in improving pipeline velocity?
  2. Fave SaaS resources and reading materials?
  3. What are the biggest mistakes people make in pipeline velocity?

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

I am so excited to welcome Johnny Chin, Founder & CEO @ Bannerman to The Official SaaStr Podcast today. Bannerman is the company that provides on demand security staff and bouncers to some of the world’s biggest companies including Spotify, Y Combinator, Weebly, Optimizely and many more incredible firms. Bannerman are also an alum of YC having been in their YC S14 Class.

In Today’s Episode You Will Discover:

  • Why did Johnny decide to transition Bannerman from B2C to B2B? WHat metrics suggested to Johnny that product market fit had not been achieved with the B2C model?
  • How did the transition affect the product? What does Johnny mean when he discusses ‘Wizard Of Oz’ moments?
  • How did Johnny go about developing and establishing a sales process? What were the inherent challenges and how did JOhnny combat them?
  • At what stage did Bannerman reach profitability and what does this allow Bannerman to now do and focus on? SHould it be a priority over growth for other SaaS businesses?
  • How Johnny approaches brand building at Bannerman? Why brand is so important for B2B companies? What are the must do’s and the must not’s when it comes to B2B branding?

In a round we call the 60 Second Saastr, we also hear:

  1. Most challenging element of the journey?
  2. Fave SaaS resources and reading materials?
  3. Competitive landscape for on demand security?

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

To Commemorate the 3 month anniversary of the best conference ever, SaaStr Annual 2016. We thought we would take a trip back to the conference with one of our favourite discussions featuring Jason Lemkin, Founder @ SaaStr and John Somorjai, Executive Vice President of Corporate Development & Salesforce Ventures. Salesforce Ventures invests in the next generation of enterprise technology. The Salesforce Ventures portfolio includes companies such as Box, DocuSign, Dropbox, Evernote, GainSight, MongoDB, MuleSoft, Stripe, SurveyMonkey, Twilio, and Xactly. Salesforce.com has invested in more than 150 enterprise cloud startups in 11 countries since 2009.

In Today’s Episode You Will Learn:

  • What have been the fundamental determinants for the growth and acceleration of Salesforce in the last few years?
  • What gave Salesforce the conviction to deploy $500m back into startup investing?
  • With the success of Salesforce Ventures, how have John’s investing goals changed since 2009?
  • Why should founders raise with Salesforce, what is the value add?
  • What is John attitude to the recent pessimism in the valley? How does John approach the dichotomy of growth and reducing burn?

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

 

Following our meeting at SaaStr Annual 2016, I am thrilled to welcome David Cancel. Now David really is a serial entrepreneur having founded 5 companies, with the last, Performable, being acquired by Hubspot, resulting in his taking up the position as Chief Product Officer at Hubspot. Now David is the CEO @ Drift. Drift allows you to talk to your website visitors and customers in real time. David is a master when it comes to hiring, company culture creation and maintenance and team building and we dig into all that in today’s episode, as well as:

  • Why David’s golden rule to recruiting is hiring people not skills?
  • Why is cultural fit so important for future employees? How can you test for it in an interview? Can you hire a team of all A team players without having insane competition and friction?
  • What does David mean when he says it is important for candidates to be scrappy? What signals are there that the person is an insane hustler?  
  • What questions does David pose to get the candidate out of the standard interview style answering? How does david push them out of their comfort zone?
  • Why does David believe it is crucial to never hire PMs who have done it before? What is the benefits of this?
  • How does David view success? What commonalities does David se in thementiality fo those that have and have not been successful?

In a round we call the 60 Second Saastr, we also hear:

  1. Must read books for startup CEOs?
  2. What are the 3 biggest lessons you learnt the hard way?
  3. What is David’s approach to learning?

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

Delighted to welcome Jon Miller to The Official SaastrPodcast today. John is the Founder & CEO @ Engagio, the all inone account based marketing platform that allows you to accelerateyour move to account based marketing, streamline account basedreporting and analytics and map salesforce leads to targetaccounts. Prior to Engagio, Jon was the Co-Founder and CMO atrocketship, Marketo.

 

Intoday's show with Jon we discuss:


  • Whatreally is account based marketing and how does it differ to otherforms of marketing?

  • Whatwere Jon’s biggest takeaways from co-founding Marketo and watch itscale into hyper-growth mode?

  • Howcan startups determine whether account based marketing is the rightmarketing solution for them? How can startups accelerate theprocess of moving to account based marketing?

  • Howcan startups communicate with their ideal customers in a nongimmicky, personalised fashion? What can be done to show personaland effective touches?

  • Towhat extent does account based market intersect with account basedsales development? How much of a role will this integration play inthe future?

 

In a round we call the60 Second Saastr,we also hear:


  1. Themost effective ABM channels?

  2. Thebiggest mistakes startups make in ABM?

  3. Thehardest element of growing Engagio from scratch?

 

If you would like to find outmore about the show and the guests presented you can follow us onTwitter here:

Joining us today on The Official Saastr Podcast is Laura
Behrens Wu, Laura is the Founder & CEO @ Shippo, the API and
dashboard for all your shipping needs.
They have raised from the likes of SoftTech,
500Startups, SLow Ventures and many more incredible investors. In
today's show with Laura we discuss:


 



  • What
    are API’s and what do they allow us to do?

  • With
    API’s developer adoption is crucial, what has worked for Laura in
    terms of finding developers, onboarding them and ensuring developer
    retention?

  • How
    much of a role does content marketing and education play in a
    complex product and tech stack, like Shippo? What strategies have
    been the most successful in educating potential
    clients?

  • Why
    does Laura believe transparent pricing is so fundamental? How does
    Laura harness the freemium model while attempting to onboard large
    corporate clients

  • What
    do the next 20 years hold for Shippo? What will it take to reach
    the milestones?


 


In a round we call the
60 Second Saastr,
we also hear:



  1. Most
    challenging element of building Shippo?

  2. Biggest advice to SMB’s on shipping
    options?

  3. The
    fundraising process: What was it like?


 


If you would like to find out
more about the show and the guests presented you can follow us on
Twitter here:


Welcome to Episode 15 of The Official Saastr Podcast. Joining me today, I am delighted to welcome, Nicolas Dessaigne. Nicolas is the CEO and Co-Founder of Algolia, Algolia are a brilliant case study for the successful pivot, having started off life as an offline search engine for mobiles but really took off by helping companies deliver an intuitive search-as-you-type experience on their websites and mobile apps. They participated in Y Combinator's Winter 2014 batch and raised $18.3M in May 2015 from the likes of Accel Partners, Point Nine Capital, Storm Ventures and many more incredible investors. and in today's show with Nicolas we discuss:



  • Why is company culture so important and was it fundamental for Nicolas and Julien to have this outlined from the beginning?

  • How did Nicolas implement the vision for the company future when founding the Algolia?

  • How does Nicolas look to balance the scaling of the business with maintenance of company culture?

  • What were Nicolas' biggest takeaways from his time at YC? 

  • How can SaaS startups optimise the fundraising process to also be a source of business development?


In a round we call the 60 Second Saastr, we also hear:



  1. Hiring Your First VP of Sales: When and What Questions To Ask?

  2. Nicolas' favourite SaaS resource?

  3. What would Nicolas do differently if he were to start the journey again?


If you would like to find out more about the show and the guests presented you can follow us on Twitter here:



 


 

On the show today I am thrilled to welcome Russell Glass, Head of Products For LinkedIn Marketing Solutions. Formerly founder, president and CEO of Bizo, a B2B audience marketing and data platform which he, from founding in 2008 to $50mm+ revenue run-rate and over 150 employees before being acquired by LinkedIn for $175mm in August of 2014 he really is a Serial technology entrepreneur, having founded or held senior positions at four venture-backed technology companies. If that wasn’t enough he is also the Co-author of The Big Data-Driven Business: How to Use Big Data to Win Customers, Beat Competitors, and Boost Profits 


In today's show with Russell we discuss:



  • What did Russ and the Bizo team do effectively that allowed them to scale, leading to their acquisition by Linkedin?

  • Is customer focus a constraint on long term growth and how can you communicate this long term vision to your investors?

  • How important a role will data play in the future of content marketing?

  • How can SMB marketers determine which platforms will be most effective for them?

  • To what extent can content marketing reduce customer acquisition? What are the other benefits?


In a round we call the 60 Second Saastr, we also hear:



  1. Who Is Doing SMB Marketing Most Impressively At The Moment?

  2. The Biggest Leanring Curve From Being Acquired By LinkedIn?

  3. What SaaS resource or blog is a must for Russell?


If you would like to find out more about the show and the guests presented you can follow us on Twitter here:


Joining us today, I am delighted to welcome Mark Woodward CEO @ Invoca - software that helps marketers drive revenue with call intelligence. Invoca has built a platform that addresses the top concern for enterprise CMOs today — delivering personalized customer experiences across devices and channels. They have backing from the likes of Upfront Ventures who wrote this on Invoca's recent $30m raise (http://www.bothsidesofthetable.com/2016/03/30/inside-scoop-funding-environment-might-mean/)  and in today's show with Mark we discuss:



  • Question from Mark Suster: How does Mark feel taking the contrarian approach that phone calls are alive and growing?

  • How was Invoice's journey to raising $30m in funding? What were the challenges? What was unexpected?

  • What all new CEOs must know coming into a new role?

  • How can a new CEO implement a new company culture and management style without disrupting the existing one?

  • What does IPO ready look like in a company? What are the requirements before you consider that newt step?


In a round we call the 60 Second Saastr, we also hear:



  1. The most crucial characteristic of all good CEOs?

  2. Biggest lesson from being a 3 time CEO?

  3. If Mark could start the process again, what would he do differently?


If you would like to find out more about the show and the guests presented you can follow us on Twitter here:


Joining us today, I am delighted to have Daniel Chait, Founder & CEO @ Greenhouse - software that gives people the power to build great companies. Greenhouse automates and simplifies the best practices for recruiting top talent, continuously monitors your recruiting activity, and automatically suggests improvements. They have backing from the likes of Social Capital, Benchmark and Felicis Ventures and in today's show with Daniel we discuss:



  • How Daniel views the hiring funnel and how you can get a consistent stream of high quality incoming candidates?

  • How can individuals breach the knowledge gap of not knowing what to look for in a iOS developer, for example?

  • How important is a strong company culture when interviewing candidates?

  • How can recruiters test candidates to ensure that their culture and skills align with the company?

  • When did Daniel hire his first Head of Sales and what was the catalyst for causing this hire?


In a round we call the 60 Second Saastr, we also hear:



  1. The Candidate Experience: How Can We Optimise It?

  2. Who Does Daniel Most Respect & Admire With Regards To Their Recruitment?

  3. What Is Daniel's Fave Hiring Blog Resource or Newsletter?


If you would like to find out more about the show and the guests presented you can follow us on Twitter here:


I am thrilled to welcome, Ajay Agarwal, Managing Director @ Bain Capital Ventures, where he focuses on early stage application software and SaaS investing. Included in his immense portfolio are the likes of Optimizely, SendGrid and GainSight, just to name a few and prior to crushing the world of investments, Ajay was an early employee at Trilogy, where as Head of Sales and Marketing he was instrumental in growing their annual revenue to $300m. 


Discussed In Today's Show:



  • What is the difference between SaaS and Enterprise Software? (there is one!)

  • How does the introduction of cloud software affect the sales cycle for startups?

  • How can startups know when is the right time to release their MVP without having significant issues with churn?

  • What does product market fit really look like for SaaS startups?

  • Once product market fit is achieved, is it merely a case off during money into the machine? 

  • Why has customer success become such an integral part of SaaS and what can startups do to optimise customer success?


In a round we call the 60 Second Saastr, we also hear:



  • Why is the system of record the easiest way to build a $bn company?

  • The $10bn opportunity in marketing? 

  • The future of zenefits?


If you would like to find out more about the show and the guests presented you can follow us on Twitter here:


Welcome to Episode 10 of The Official Saastr Podcast. To celebrate this milestone, we have a very special guest: Mathilde Collin. Mathilde is the CEO and Co-Founder of Front, one of the world's most innovative young SaaS startups working in the space of email collaboration and in today's show with Mathilde we discuss:



  • Mathilde's experience as a young founder and CEO in the enterprise space?

  • How did Mathilde manage to attract some of the world's top talent and hire effectively?

  • What were her biggest takeaways from her time at YC? 

  • Why did Mathilde decide to raise US funds rather than European?

  • How has the evolution of content marketing altered Front's sales strategy? 


In a round we call the 60 Second Saastr, we also hear:



  1. Hiring Your First VP of Sales: When and What Questions To Ask?

  2. Mathilde's favourite SaaS resource?

  3. Compare UK to US investor mindsets?


If you would like to find out more about the show and the guests presented you can follow us on Twitter here:



 


 

This episode was recorded at Saastr Annual 2016 featuring Jason Lemkin, Founder @ Saastr and Josh Stein, Partner @ DFJ. For those that do not know, Josh is arguably one of the most successful investors in the SaaS space having backed the likes of Box, Twilio, Yammer and many more from the very earliest of stages.


In Today's Show We Cover:



  • What is the fundamental differing between a great and a good CEO in SaaS?

  • Is it possible to learn to become a great CEO?

  • What did Aaron Levie do to enable Box to scale so successfully?

  • How can startup founders determine whether they have the ability to go the distance as CEO?


If you would like to find out more about the show and the guests presented you can follow us on Twitter here:



If you enjoyed the conversation with Keith today and want to save your space at what promises to be the best Saastr Annual ever, Saastr Annual 2017! You can buy early bird tickets here!

This episode was recorded at Saastr Annual 2016 and it is an incredible conversation whereby Jason Lemkin deep dives into the career and wisdom of Keith Rabois. For those that do not know, Keith is a legend of the tech industry having helped build some of the most important companies in Silicon Valley including Paypal, Square and Linkedin. He is also a very prominent VC with Khosla Ventures and has recently rejoined the world  of operations, looking to disrupt the world of property with OpenDoor.


For your chance to win a signed copy of Jason's new book 'How Hyper Growth Companies Create Predictable Revenue', we would be so grateful for you to upvote the episode on ProductHunt!


In Today's Show We Cover:



  • Why Keith rejoined the world of operations having been a VC with Khosla?

  • Is domain expertise a good or a bad thing to have when entering an industry?

  • When hiring, how do you achieve the balance of experience and potential?

  • When is the right time to hire a COO? What are the signs?

  • How Did Keith approach hiring in high growth rocketship companies?


If you would like to find out more about the show and the guests presented you can follow us on Twitter here:



If you enjoyed the conversation with Keith today and want to save your space at what promises to be the best Saastr Annual ever, Saastr Annual 2017! You can buy early bird tickets here!

I am thrilled to welcome, Doug Pepper, Partner @ Shasta Ventures to the show today. Doug is a master when it comes to SaaS investments with his companies generating over $500m in revenue in 2015, having funded the likes of Marketo, Optimizely and Flurry. In today's show with Doug we discuss: 



  • How Doug made his approach into investing?

  • What metrics are required for startups to get Series A investors interested?

  • What are the guidelines for a startup to manage their burn rate?

  • In future tough markets, we will see greater consolidation?

  • How can startups stand out when selling to CIO, CEO's and VPs? 


In a round we call the 60 Second Saastr, we also hear:



  1. What has been the scariest moment of Doug's VC career?

  2. Why Doug is so excited for the future of mobile SaaS? 

  3. What the main effects are of the rise of bottoms up sales strategies?


If you would like to find out more about the show and the guests presented you can follow us on Twitter here:


Joining us today, I am delighted to have Russell Fujioka, US President at Xero, the world's fast growing SaaS company making accounting software beautiful. Prior to joining Xero, Russ was the Global Vice President of Marketing at Dell, EIR at Bessemer Venture Partners and held executive roles at the likes of Adobe. In today's show with Russ we discuss:



  • How Russ came to be US President at the world's fastest growing SaaS company?

  • How has Russ seen the SaaS industry change over his 25 years?

  • Why does Russ believe all the SaaS best companies are founder led?

  • What were the determinants that allowed Adobe to go from 40m to $1bn?

  • How does Russ view the current competitive landscape for accounting software? 

  • What were the main benefits of experiencing the VC industry with Bessemer?


In a round we call the 60 Second Saastr, we also hear:



  1. Which pubic markets SaaS company does Russ most respect?

  2. Russ' favourite SaaS resource?

  3. Is accounting software a winner take all market?


If you would like to find out more about the show and the guests presented you can follow us on Twitter here:


It is a huge honour to welcome, Mamoon Hamid, Partner @ Social Capital. One of the world's best performing funds with investments in the likes of Slack, Box, Intercom, Yammer and many more incredible companies. Prior to joining Social Mamoon was a Partner at US Venture Partners (USVP) and in today's show we discuss:



  • How Mamoon made his way into the world of investing and VC?

  • What were Mamoon's biggest takeaways from seeing the rocketship growth of the likes of Slack and Box? What were their challenges faced?

  • What is the distinct value proposition of Social over other VC funds? How do you look to differentiate?

  • What has been the effect of the rise of the bottoms up sales apprcach and what role will this play in the future for selling to enterprise clients?

  • Which company will be the first to make a million on Slack? 


In a round we call the 60 Second Saastr, we also hear:



  1. Biggest challenge facing Mamoon and Social Capital?

  2. Mamoon's favourite SaaS resource?

  3. Biggest piece of advice to SaaS founders?


If you would like to find out more about the show and the guests presented you can follow us on Twitter here:



 

I am thrilled to welcome, Shardul Shah, Partner @ Index Ventures to the show today. Shardul is the sole member of the Index team to have worked in all Index's offices around the world in Geneva, London and SF. Now in SF, Shardul focuses on security, software and infrastructure with investments in the likes of Squarespace, DropBox and Adaloom, just to name a few. 


Discussed In Today's Show:



  • How Shardul made his unorthodox approach into investing?

  • What Shardul really looks for in early stage SaaS products when investing?

  • Why is reducing time distance to value so important for a SaaS product?

  • How can startups effectively sell to CSO's in this new wave of cyber security?

  • What are the risks and flaws of the open source community? 

  • How can enterprise SaaS products create true customer stickiness?


In a round we call the 60 Second Saastr, we also hear:



  1. What is Shardul most concerned about in the SaaS space?

  2. Shardul's favourite SaaS resource: 

  3. Which public markets SaaS companies is Shardul most impressed with?


If you would like to find out more about the show and the guests presented you can follow us on Twitter here:


Joining us today, I am thrilled to welcome, Mark Geene, CEO @ Cloud Elements the cloud API integration service that uses uniform APIs to connect your application with entire categories of services. Prior to joining Cloud Elements, Mark has had over 20 years experience in the industry including executive roles with IBM and Oracle and in today's show with we discuss:



  • What was the origin story behind Cloud Elements and how Mark became CEO?

  • What does it take for a company to transition from a 50 person company to a 500 person company?

  • How does Mark apply lean startup methodology to SaaS?

  • When is the right time to really invest in sales and marketing?

  • Does the lack of SaaS exits greater than $500m concern Mark? 

  • Why have we seen the rise of the API economy and what does the future hold?


In a round we call the 60 Second Saastr, we also hear:



  1. What lesson has Mark learnt recently that changes the way he works?

  2. Mark's favourite SaaS resource?

  3. Vertical vs platform SaaS play?


If you would like to find out more about the show and the guests presented you can follow us on Twitter here:



 

Joining us today, I am thrilled to welcome, Andy Lark, CMO at Xero, the world's fast growing SaaS company making accounting software beautiful. Prior to joining Xero, Andy work with the likes of Dell, Sun Microsystems and The CommonWealth Bank Of Australia and in today's show with Andy we discuss:



  • How Andy came to be CMO at the world's fastest growing SaaS company?

  • How Andy structures his team?

  • What does Andy make of the expansion of the traditional marketing role?

  • How to approach branding with regards to competitors?

  • How did Tiago choose his investors? 

  • What are the main differences of the old enterprise world compared to selling SaaS to SME's today?


In a round we call the 60 Second Saastr, we also hear:



  1. What lesson has Andy learnt recently that changes the way he works?

  2. Andy's favourite SaaS resource?

  3. How does Andy approach the issue of work life balance?


If you would like to find out more about the show and the guests presented you can follow us on Twitter here:



 

Welcome to Episode 1 of The Official Saastr Podcast, the show will delve behind the scenes of the latest and greatest SaaS rocketships talking to the founders and operators themselves. We will also be chatting with the investors and VCs funding these hyper growth companies to reveal their tactics and strategies when it comes to deciding whether to invest. 


To celebrate, we have a very special guest: Tiago Paiva. Tiago is the CEO and Co-Founder of Talkdesk, the world's leading browser -based call center software solution and in today's show with Tiago we discuss:



  • The Origin Story For TalkDesk

  • How Tiago achieved $3m in Sales without spending a $ on marketing

  • When is the right time to hire your VP of Sales? 

  • How important is it for SaaS startups and founders to be in SF?

  • How did Tiago choose his investors? 


In a round we call the 60 Second Saastr, we also hear:



  1. The biggest challenge Tiago has faced to date?

  2. Tiago's favourite SaaS resource?

  3. What role is the hardest to fill in a SaaS organisation?


If you would like to find out more about the show and the guests presented you can follow us on Twitter here:



 


 

Janine Pelosi is the CMO @ Zoom, the next-generation enterprise phone system. Prior to their very successful IPO, Zoom raised funding from some of the best in the business including Sequoia, Emergence Capital, Horizons Ventures and 2 of my favourites in the form of Matt Ocko @ Data Collective and Dan Scheinman. As for Janine before joining Zoom, she spent 11 years at Cisco where among many incredible achievements she led worldwide demand gen for WebEx and led their worldwide digital marketing team with a $25M annual budget. 

In Today’s Episode We Discuss:

  • How Janine made her way into the world of SaaS and came to be one of the leading CMOs today with Zoom?
  • How has the role of the CMO changed over the last 5 years? Would Janine agree with Jason Lemkin that “the role of the CMO is to execute the vision of the CEO”? What makes Janine and Eric’s relationship so successful? What makes Eric the special leader that he is? How does the changing power of the CMO affect their relationship with the CEO?   
  • When is the right time for startups to hire their first CMO? What should they look for in that ideal candidate? What should they have in place in terms of infrastructure, prior to hiring the candidate? What does the right onboarding process look like for a CMO? Where does Janine see many going wrong when hiring their first CMO? 
  • How does Janine look to create alignment between sales and marketing? Why does Janine not believe in having the labels of “MQLs and SQLs”? How does Janine look to reduce the friction when handing off between marketing and sales? What are the common causes? How are we seeing marketing also blend with customer success?

Janine’s 60 Second SaaStr:

  1. What does Janine know now that she wishes she had known at the start of her time at Zoom?
  2. Who does Janine most respect in the world of marketing today? Why?
  3. What would Janine most like to change about the world of SaaS today? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Janine Pelosi

Matt Schatz is SVP of Sales at WPEngine, responsible for defining and executing the global sales strategy. Matt has nearly two decades of senior leadership experience in sales and customer growth, specifically for technology companies with customers around the world including Bazaarvoice, CityVoice and Rackspace.

 

Missed the session? Here’s what Matt  talks about:

  • Getting your “first story”
  • What is a lucky lead and how does that turn into predictable growth
  • Building trust across time zones

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Allison Pickens is the COO @ Gainsight, the company that provides everything you need to turn your customers into your biggest growth engine. To date Gainsight have raised over $184m from some of the world’s best VCs in the form of Lightspeed, Bessemer, Insight Venture Partners, Battery Ventures and Salesforce Ventures just to name a few. As for Allison, in her 5 years at Gainsight her list of achievements in endless from running all functions that drive value for Gainsight customers, now a 150 person team, to building out the corporate development function to being the right hand to the CEO. Allison is also an Entrepreneur-In-Residence at Bessemer Venture Partners and sits on the board of RainforestQA. Before Gainsight, Allison started her career in NYC with stints at Bain and The Boston Consulting Group.

In Today’s Episode We Discuss:

  • How Allison made her way into the world of SaaS with Gainsight from her start in finance at Bain in New York?
  • What does a strategic plan really mean to Allison? What is included in it? How should it be structured? In terms of ambition, how does one set ambitious enough plans to be a stretch but not a stretch too far? How does one tie their strategic plan to their financial plan? What is the right way to communicate this throughout the organisation?   
  • Why does Allison believe product marketing and customer success are the new sales and marketing? What have been Allison’s biggest lessons on how to effectively measure adoption? Who is accountable to this number? CS or product management? Does Allison believe that marketing needs to be held accountable to a number directly tied to revenue? 
  • How does Allsion respond to the common negative of “services revenue”? What is an acceptable ratio of services to software revenue? How can one approach setting up a services team for scale? Why is having such a great CS team actually bad for product development in the long run? How can one mitigate this?

Allison’s 60 Second SaaStr:

  1. What does Allison know now that she wishes she had known at the beginning of her time with Gainsight?
  2. How often should CS check in with their customers? What does that look like? 
  3. If on a tight budget, how should one staff a CS team?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Allison Picken

Building a company made up of distributed teams presents a plethora of complex challenges that can derail productivity and impact employee retention. But with it comes immense benefits and competitive advantages such as the diversification of ideas, speedier product development, and representation in important regions and time zones. Come and hear about the typical pitfalls (and how to avoid them) from Pat Poels, an executive with over seven years under his belt leading Eventbrite’s now 300+ strong engineering team that sits across North America, South America, and Europe

 

Missed the session? Here’s what Pat  talks about:

  • Engineering your own luck
  • How to build an engineering team

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Jon Herstein is the Chief Customer Officer at Box, the company that provides one platform for secure content management, workflow and collaboration. Prior to their IPO, Box had raised funding from some of the best in the business including Andreesen Horowitz, Bessemer, DST, Emergence and Meritech, just to name a few. As for Jon, prior to being Chief Customer Officer at Box, he was Senior VP of Customer Success, responsible for all post-sales services Box provides from implementation to user adoption and more. Before Box, Jon spent 4 years as VP of Professional Services at NetSuite and prior to that, close to 8 years as Senior Director of professional services at Informatica.

In Today’s Episode We Discuss:

  • How did Jon make his way into the world of SaaS and come to be one of the leading figures in the rising tide of the customer success movement?
  • What does Jon mean when he says, “you have to constantly bring your customers to the forefront of your employees minds”? For non-customer facing roles, what can one do to give them that perspective? Does it work to ensure every function spends time in customer support? What is challenging about that? What can be done in the onboarding phase to ensure the individual has the most empathy for the customer, regardless of function?  
  • For those in CS, what is the right communication cadence to check in with their accounts? What should the agenda look like? What outcomes should they drive towards? Should they be involved in the upsell process? How does Jon think about post-mortems on churned clients? How do they structure them? What lost client stands out to Jon and what would he have done differently to retain them?
  • From Jon’s experience seeing Box in hyperscaling, at what stages do SaaS orgs start to break down? Why does Jon think that is? What can be done to proactively try and mitigate this? How does Jon think about the structuring of roles and responsibilities with scale? What does this done well look like? Where do many people go wrong here?  

Jon’s 60 Second SaaStr:

  1. What does Jon know now that he wishes he had known at the beginning of his time with Box?
  2. What motto or quote does Jon frequently revert back to?
  3. What is the most challenging element of Jon’s role with Box today?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Jon Herstein

Ever feel like you can’t really connect with prospects or have an organized workflow to get deals closed? Outreach.io, the leading Sales Engagement platform, supports sales reps and their managers by making it simple to humanize and personalize communication at scale; automating the soul-sucking manual work; and dramatically increasing the productivity and efficiency of all revenue-generating teams. You can check them out at outreach.io/saastr to chat with them and receive a free copy of their new book -- Sales Engagement: How The World's Fastest-Growing Companies are Modernizing Sales Through Humanization at Scale.

 

Tom Bogan, CEO of Adaptive Insights, a Workday company, will review the key principles to building a successful SaaS company. From team to vision to metrics to funding and more, these principles provide the framework for high-growth, high performing SaaS companies.

How can you develop a winning culture? How can you set aggressive but realistic goals? What’s needed to build the right team in SaaS today?

Missed the session? Here’s what Tom talks about:

  • The important maxims about team building
  • Insights on fundraising and why you might not want to always raise at the highest valuation
  • Personal stories from his time building Adaptive Insights

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Whitney Bouck is the COO @ HelloSign (now a part of Dropbox). For those that do not know, HelloSign is the company reimagining how you approach your most important business agreements with their award-winning e-Sign solution. As for Whitney, she directly leads the organization's go-to-market efforts, including sales, marketing, business development and customer operations. Whitney is also an advisor to companies funded by the YC Continuity Fund, focusing on enterprise strategy, go-to-market strategy, leadership and execution. If that was not enough, Whitney is also on the board of Ekata, building the global standard in identity verification. Finally, prior to HelloSign Whitney spent close to 5 years at Box where as SVP Global Marketing & GM Enterprise she took on all of marketing globally for Box and was responsible for reshaping the company brand from SMB to enterprise. 

In Today’s Episode We Discuss:

  • How Whitney made her way into the world of SaaS originally with Box and how that led to her coming one of today’s leading COOs with HelloSign? What were Whitney’s biggest takeaways from seeing the hypergrowth of Box? How did that change her operating mentality?
  • What does truly successful exec leadership look like in Whitney’s mind? When is the right time for founders to think about building out their first exec team? What common mistakes do they make in the process? What can founders do to attract seasoned SaaS execs to their early-stage company? What are the questions that suggest an individual has a startup culture to them? What are the indications that they are a “big company” person?  
  • What does Whitney believe is the new role of the CIO? What has changed about their tole and what has driven this change? With their coming front and centre in the org, how does that change both the reporting and operating structure of the business? What are the nuances and intricacies of this role that many do not often consider? 
  • COO is thrown around as a term today, what does it really mean to Whitney? What does Whitney believe separates good from great when it comes to COOs? When is the right time for founders to start looking for their first COO? What should they look for in their first COO? What is the optimal onboarding process for any new COO? 

Whitney’s 60 Second SaaStr:

  1. What does Whitney know now that she wishes she had known at the beginning?
  2. What makes for the optimal relationship between COO and CEO?  
  3. What is the most challenging element of Whitney’s role with HelloSign today?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Whitney Bouck

 

Globalization opens up a world of opportunities for sales growth. We often focus on the positive sides of growth—but what about taking a look at the ugly sides? Even what we could consider “good problems” need preparation, and it starts by understanding your team and your goals, including knowing when and how to recruit members of your team, and building in a way that compliments your growth. Do you need more man-power on the customer facing side, or do you need to bring in new management to keep everything in line? Growth isn’t always linear, and the steps to success aren’t always one after the other. How do you prioritize and organize to bring the best possible results? This side of success can be scary, but knowing how to prepare can set you up to reach your companies long term growth goals.

 

Missed the session? Here’s what Tara talks about:

  • What does the ideal candidate look like?
  • How to hire your core staff really well
  • Enabling salespeople to share learnings

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Companies that have access to more accurate financial data have the ability to develop seamless exchanges of information, providing consumers with improved ways to manage their finances. But how do companies gain secure access to that data in the first place? Enter the platform company. Hear from Plaid co-founder and CEO, Zach Perret and CNBC's Ari Levy as he walks through his lessons learned building Plaid and how it found itself at the center of the fintech ecosystem.

 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Zach Perret

Justin Welsh is the former SVP Sales @ PatientPop, the startup that offers the first all-in-one practice growth platform that’s HIPAA-compliant and is proven to grow your practice. During his 5 years at PatientPop, Justin grew sales from $0 to $56m alongside the full build-out of the sales team. Before PatientPop, Justin was one of the first 10 employees at ZocDoc, where he spent 4 years in different roles including Director of Strategic Sales. 

In Today’s Episode We Discuss:

  • How Justin made his way into the world of Sales and came to be one of the industry's leading scale up Sales leaders with PatientPop and ZocDoc?
  • How did Justin experience burnout? What were the first indications and signals for him that he was suffering from it? How did it manifest itself in how he carried himself and his behaviour? How did Justin communicate the situation to his bosses? What does Justin advise others in communicating burnout to their superiors?  
  • As a manager observing their team, what are signs that an individual is burning out? What is the right way to approach them to discuss the situation? What options do managers have available to them when faced with a burned out employee? How does micro-management fit into the signals that suggest clear burnout of the individual? 
  • Justin has said before that “culture must precede performance”, what did he mean by this? What actions and communications must they adopt to ensure that this feeling of culture over performance is accepted by the team? With that in mind, how does Justin think about KPI and goal-setting? What can leaders do to create an environment of safety for their team? Where do many leaders go wrong here? 
  • Having seen multiple scaling culture, where do SaaS organisations tend to break down both in terms of culture and process? What are those inflection points? What can be done to actively mitigate these 2 significant points of failure?   

Justin’s 60 Second SaaStr:

  1. What does Justin know now that he wishes he had known when he started at PatientPop?
  2. Sales leader Justin most respects and why?
  3. If Justin could change one thing about the world of SaaS today, what would it be? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Justin Welsh

As a global technology provider powering thousands of SaaS companies, Google is at the forefront of driving exciting and innovative technologies to market. Eyal and Megan host a fireside chat between Google Cloud and Zenoss, a leader in software-defined IT operations. They discuss the most common and emerging challenges facing SaaS companies today. You’ll also learn how leading SaaS companies are able to scale and thrive in this complex, dynamic environment. Join us for this lively discussion between two innovators.

 

Missed the session? Here’s what Eyal and Megan talks about:

  • How to develop software faster
  • The emergence of new A.I. services
  • Why the “strongest” conversations need to happen between engineering and marketing

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

 

Vikas Bhambri is SVP Sales and Customer Experience @ Kustomer, the startup providing Real-time, actionable views of customers with continuous omnichannel conversations and intelligence that automates repetitive, manual tasks. To date they have raised over $113m in financing from some of the best in the business including Tiger Global, Battery Ventures, Boldstart, Canaan, Cisco and Redpoint just to name a few. Prior to Kustomer, Vikas spent over 20 years implementing, consulting, marketing, and selling CRM and ContactCenter solutions with companies like LivePerson and Oracle. 

In Today’s Episode We Discuss:

  • How Vikas made his way into the world of SaaS and came to be at the rocketship that is Kustomer?
  • Why does Vikas believe that a wave of SaaS incumbents are about to be displaced or disrupted? What about the changing tech stacks and infrastructures makes them vulnerable to up and comers? Does this not lead to a consolidatory environment? How does Vikas see the space play out in the coming years when it comes to acquisitions?
  • What have been the dramatic changes that have happened in sales over the last few years? What is the right way for startup founders to address sales rep onboarding? Why is it so crucial to invest in enablement in the early days? How should this enablement be structured? How does this change sales rep payback periods? What is a good payback period? 
  • How does Vikas feel about discounting? If accepted, what must the startup ask for in return? How does Vikas think about multi-year deals? When are they good? What sort of terms make them less beneficial for the vendor? 
  • How does Vikas think about professional services? What is a good margin for professional services? What ratio of revenue is healthy for professional services to account for? When should one look to hire their first customer success reps? What should they look for in those reps? 

Vikas’ 60 Second SaaStr:

  1. What does Vikas know now that he wishes he had known at the beginning?
  2. What is his secret to building diverse teams?
  3. The sales leader Vikas most respects and admirers and why?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

The age-old sales funnel has worked fine for decades…until now. Flaws are being exposed, and a new model is imminent. Why is the sales funnel alone, no longer an appropriate way thinking about customers? What will emerge to supplement or replace it? Hubspot CEO Brian Halligan and NEA's Hilarie Koplow-McAdams explore the evolution of the marketing and sales funnel you’ve been using for decades to generate traffic and convert and leads into customers.

 

Missed the session? Here’s what Brian talks about:

  • Why a flywheel instead of a funnel?
  • What does the Grateful Dead have to do with Marketing…?
  • What role do T shaped people play?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Brian Halligan

Leah is currently a General Partner at Fuel Capital, an early stage venture fund located in Silicon Valley. She likes to invest across consumer, B2B saas, and technology infrastructure companies at the earliest stages. n 2008 Leah founded TaskRabbit, the leading on-demand service marketplace in the world. She spent nearly a decade involved with the company as CEO and Executive Chairwoman before she sold the company to IKEA in October of 2017. Hear about her takeaways from a product reboot with TaskRabbit.

 

Missed the session? Here’s what Leah talks about:

  • What are the lessons learned from a product reboot?
  • When  bringing a product to market - what are the BHAGs?
  • How to navigate a product pivot.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Leah Busque

Eric Christopher is the Founder and CEO @ Zylo, the software management system built for the cloud pioneering a new standard in software management. To date, Eric has raised over $12m for Zylo from some of the best in the business including Byron @ Bessemer, Salesforce, GGV, Semil @ Haystack and the team at High Alpha. Prior to founding Zylo, Eric was the VP of Sales @ Sprout Social leading the revenue operations for over 11,000 customers. Before Sprout Social he was VP of Sales at Shoutlet, responsible for global direct and channel sales teams and developing and managing strategic relationships. Finally, prior to Shoutlet, Eric spent over 7 years at ExactTarget as a Senior Business Development Manager which is where he met High Alpha’s Scott Dorsey. 

In Today’s Episode We Discuss:

  • How Eric made his way into the world of startups and SaaS? What were his biggest takeaways from working with Scott Dorsey @ ExactTarget? What was the founding moment with Zylo?
  • What have been Eric’s biggest lessons when it comes to making the transition from founder led sales to sales team? What would we have done differently with the benefit of hindsight? What were the biggest challenges in the process?  
  • How does Eric think about the importance of quantity vs quality of logos when acquiring your first few customers? Do big logo brand names really provide social validity or is it over-hyped? How does Eric think about discounting in the early days? What can founders do to really extract the most value from the discount they are giving away? 
  • Why does Eric believe that hitting the employee 50 mark is a huge moment for founders and the scaling of the company? What fundamentally changes? What gets harder? What gets easier? How has Eric seen his role evolve with the scaling of the team? How does Eric think about goal and KPI setting with a much larger team? What needs to change? How does one create and retain accountability and ownership at scale?
  • Why does Eric believe that the bar for execution in SaaS in 2019 is so much higher than in 2009? What has changed? How does this make Eric change the way he approaches benchmarking, capital allocation and growth? How did Eric find raising the Series A as a non-Bay area company?

Eric’s 60 Second SaaStr:

  1. What does Eric know now that he wishes he had known at the beginning? 
  2. What is the toughest role to hire for today?
  3. If the money is on the table, take it. Agree or not? Why?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Eric Christopher

Michael Seibel is CEO and a partner at Y Combinator and co-founder of two startups – Justin.tv and Socialcam. He has been a partner at Y Combinator since 2013, advised hundreds of startups, and has been active in promoting diversity efforts among startup founders. Hear his take on the future of work with a decade in learnings from YCombinator.

 

Missed the session? Here’s what Michael talks about:

  • How quickly should you hire?
  • When is the right time to sell a startup?
  • How large a differentiator will investors make in your company?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Michael Seibel

Peter Yared is the Founder & CEO @ InCountry, the startup that allows you to operate globally with data residency as a service meaning they store your mission-critical data in it’s country of origin, without compliance. To date, Peter has raised $8m for InCountry from some of my very favourites including Bloomberg Beta, Felicis, Ray Tonsing @ Caffeinated and CRV just to name a few. Prior to InCountry, Peter founded six and sold 6 enterprise software companies that were acquired by Sun, Citrix, VMware, Oracle, Sprinklr and Prograph. Previously, Peter was also the CTO/CIO of CBS Interactive where he brought CBS into the cloud. At Sun, Peter was the CTO of the Liberty identity consortium that designed SAML 2.

In Today’s Episode We Discuss:

  • How did Peter make his way into the world of enterprise SaaS with the founding and selling of 6 companies and how did InCountry come about? What is that founding moment?
  • Why does Peter feel like it enterprise is really hard again? Why is it no longer to come into large enterprises with a small contract and expand? How does Peter think about enterprise pilots today? Do they really mean anything? What proof points suggest an enterprise is really bought in? What benchmarks should startups bake into the agreements? 
  • How does Peter think about and approach market sizing today? Why is market risk no longer a risk he is willing to take? Where do many entrepreneurs make mistakes when it comes to market timing? In terms of timing, how should entrepreneurs think about whether to start at SMB and move to enterprise or start enterprise and move to SMB? What are the considerations? 
  • Why does Peter believe that large orgs are so dysfunctional today? What can founders do to extract the truly special talent out of these large orgs with big pay packets and troves of options? How has Peter found the transition from CTO to CEO this time? What have been some of the challenges? Where has he asked for external help? 
  • Having built numerous successful remote teams, what have been Peter’s biggest learnings in what it takes to successfully build remote teams? Where do many people go wrong? Does it have to be from Day 1? When is the right time to start thinking about this as a startup?  

Peter’s 60 Second SaaStr:

  1. What would Peter most like to change about the world of Silicon Valley and tech?
  2. Who is the biggest rockstar in the valley that is less well known?
  3. Hire fast, fire fast, agree or disagree? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Peter Yared

Erica has led New Relic through massive growth, scaling the company’s enterprise business 10x since she joined the business pre-IPO. Growing a company’s revenues, customer base, team, process, and product doesn’t just happen without major work and strategy. Erica will share the five critical steps (and some lessons learned along the way) for scaling in the enterprise.

 

Missed the session? Here’s what Erica talks about:

  • How to change up your marketing mix
  • How to transition from SMB to enterprise
  • Identifying your sweet spot target customers and leveraging your network to access those companies.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Joe Chernov is the VP Marketing @ Pendo, the startup that understands and guides your users allowing you to create products they cannot live without. To date they have raised over $108m in funding from some of the best in SaaS including Meritech, Salesforce, Battery, Spark Capital and Sapphire just to name a few. Prior to Pendo Joe was Chief Marketing Officer at Robin and before that he was the CMO @ Insight Squared where he led the transition from an email-driven leads model to an account-based marketing model. Before InsightSquared, Joe was Head of Content Marketing at Hubspot where he increased blog traffic by more than 1M visits/month and increased leads by 40%. Finally, pre-Hubspot, Joe held VP of Marketing roles at Kinvey and Eloqua.

In Today’s Episode We Discuss:

  • How Joe made his way into the world of startups and SaaS marketing many years ago? Does Joe really believe in the saying that, “no one really knows what they are doing?” Where are the nuances to it?
  • Joe has been CMO and then #2 and alternated between the 2 roles many times, so what the continuous alternating? How does switching from CMO to VP of Marketing prepare you better for each subsequent role? Does Joe agree with the saying that the best in marketing are able to “throw the playbook out of the window”? 
  • What does Joe mean when he says, “the most powerful mentorship is mentorship from below”? What makes the best #2’s just so good? What do they do? What advice would Joe give to a #2 in a role today? What can the individuals do to foster a relationship of deep trust and transparency?
  • Having worked at both early and late stage companies, what does Joe believe the early companies can learn from later stage companies? Does installing very severe ops not reduce the creativity of a young company? What does Joe believe that later stage companies can really learn and take from early-stage companies? 
  • How do the marketing functions differ in both structure and process when comparing early to late stage? What does Joe find to be the biggest challenge within each respective stage? How has Joe seen the content landscape evolve and change radically throughout his career alternating between early and late stage companies?  

Joe’s 60 Second SaaStr:

  1. Who does Joe believe is killing it in SaaS marketing now? Why?
  2. ABM, total BS or real meaning to it?
  3. If Joe could change one thing about SaaS today, what would it be?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Joe Chernov

Hear from Hired's CEO Mehul Patel on how to move from transactional to recurring revenue. Hired is a marketplace that matches tech talent with innovative companies. Hired combines job matching with unbiased career counseling to help people find a job they love. Through Hired, job candidates and companies have transparency into salary offers, competing opportunities and job details.

 

Missed the session? Here’s what Mehul talks about:

  • How to leverage your company values to drive stability.
  • Hiring people, strategically.
  • Finding your pricing sweet spot.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Dropbox Chief Customer Officer Yamini Rangan draws on 20 years of experience to challenge five common misconceptions about SaaS success. From beating the competition to over (or under) relying on Outbound, she offers a practical perspective on the frameworks that are holding businesses back from reaching their full potential in a changing landscape.

 

Missed the session? Here’s what Yamini talks about:

  • How to increase the odds of reaching $1B in ARR
  • What is the pull upmarket, why do companies focus their attention there?
  • Common go-to-market myths and lessons.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

 

David Skok is a serial entrepreneur turned VC at Matrix Partners. He founded four companies: Skok Systems, Corporate Software Europe, Watermark Software, and SilverStream Software and did one turnaround with Xionics. Three of the companies he founded went public and one was acquired.

Jason Lemkin is the Founder @ SaaStr, the world’s largest SaaS community and leading early-stage SaaS fund with investments in Automile, TalkDesk, Algolia and more.

Jason Vandeboom is the Founder of ActiveCampaign, a sales and marketing automation platform that enables small businesses around the world to meaningfully connect and engage with their customers. Since 2013 with their transition to SaaS have grown to more than $50 million in ARR in less than five years, while maintaining profitability.

Dave Kellogg is a leading technology executive, independent board member, advisor and angel investor. In his most recent role, Dave was the CEO @ Host Analytics where he quintupled ARR, halved customer acquisition costs and increased net retention rates before selling the company to a private equity sponsor.

Fred Shilmover is the CEO and co-founder of InsightSquared, one of Boston’s premiere tech startups paving the way in the sales intelligence space. Throughout the InsightSquared journey, Fred has raised over $25m in VC funding from the likes of DFJ, Bessemer, Salesforce and Atlas Venture.

In Today’s Episode We Discuss:

  • Does David Skok believe that ACV should sit at the top of the metrics stack? What are the 4 metrics that fundamentally matter in your business? What can founders do to their pricing model to extract as much value from each customer? How do the very best businesses structure their pricing for value extraction?
  • If ACV increase is a core focus for our startup, should we hire a sales rep solely selling to enterprise? What are the biggest mistakes founders make in this scenario? What can founders do to optimise revenue per lead? How does on need o approach lead targeting according to the individual skills of their reps?
  • Is it best to start at enterprise and work down to SMB or does SMB and work up to enterprise work best? How does the product have to change with the scaling to enterprise? How does the messaging need to change with the scaling to enterprise? How do you need this change to be reflected in your pricing?    
  • What does it truly mean to be an ARR first company? What is the right way for founders to calculate their differing ACVs? What is the right way to present that when pitching VCs? Where do many founders go wrong in how they present and discus ACVs with investors?

Ryan Petersen will share what he has learned about scaling culture, expanding globally, raising venture capital (or not), and using technology to improve legacy industries.

 

Missed the session? Here’s what Ryan talks about:

  • How Flexport grew to a multibillion-dollar business.
  • How the company broke into the $2T freight forwarding industry.

 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Ryan Petersen

Sara Varni is the CMO @ Twilio, the company building the future of communications allowing you to engage customers like never before on voice, SMS, WhatsApp or Video. Prior to their IPO in 2016, Twilio had raised over $250m in VC funding from some of the best in venture including USV, Bessemer, Salesforce and Techstars just to name a few. As for Sara, prior to Twilio she spent 10 years with Salesforce in numerous roles including SVP of Marketing for Salesforce’s Sales Cloud and CMO @ Desk.com, among other roles. If that wasn’t enough, Sara is also an advisor @ Anthos Capital.

In Today’s Episode We Discuss:

  • How did Sara made her way into the world of SaaS and came to be one of the industry’s leading CMOs with Twilio today? What were Sara’s biggest takeaways from her 10 years at Salesforce seeing the incredible hyper-growth first hand?
  • What does Sara mean when she says, “you have to have a creative plan to get your message to market”? Does Sara really believe that there is a playbook when it comes to marketing? How does Sara determine when to throw the playbook out of the window? What resounding question do you always have to ask yourself when thinking messaging?
  • Messaging is very dependent on the customer being targeted, how does the messaging need to be different when targeting SMB vs enterprise? How does the creative plan to get the message to the target customer change dependent on SMB vs enterprise? Where does Sara see most people go wrong here?   
  • Why does Sara so strongly believe in the power of customer stories? What makes the very best customer stories? What would Sara’s advice be to someone who is wanting to start creating them? Where does Sara see so many people go wrong? What are Sara’s tips for creating this alignment between the marketing team that make the stories and the sales team that sell them? Where are there often points of tension?
  • What does the very commonly used term, “enablement”, really mean to Sara? Does it mean you can hire lower quality candidates and upgrade them? How does Sara distinguish between a stretch VP and a stretch too far? What questions does Sara find most revealing in the interview process?  

60 Second SaaStr:

  1. What does Sara know now that she wishes she had known at the beginning?
  2. Who is crushing it in the world of SaaS marketing today?
  3. What is the most common reason for the breakdown of an efficient funnel?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Sara Varni

It’s the employees’ market. There are more jobs than there are qualified people to do them. SaaS companies face sustained headwinds in the attracting, cultivating, driving productivity, and retaining talent. Your market competitors are your adversaries, but so is the entrepreneur sitting right next to you whose business is in a completely different sector. Elisa shares practical advice on how to win three key Talentshare battles, which are essential to winning the Marketshare war.

Missed the session? Here’s what Elisa talks about:

  • How to win Talentshare when the system is stacked against you.
  • How to drive synchronization, productivity when your needs are constantly evolving and the talent mix is incredibly fluid and diverse.
  • How to use Culture as the lever to maximize the ROI that you get out of the biggest investment your business will ever make.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Elisa Steele

Dave Kellogg is a leading technology executive, independent board member, advisor and angel investor. In his most recent role, Dave was the CEO @ Host Analytics where he quintupled ARR, halved customer acquisition costs and increased net retention rates before selling the company to a private equity sponsor. Before that Dave was SVP/GM of Service Cloud @ Salesforce where he led the $500m line of business for customer service applications. Finally pre-Salesforce, Dave was CEO @ MarkLogic where he grew the team from 40 to 240 and revenues from $0 to an $80m revenue run rate. If that was not enough, Dave currently or has previously sat on the boards of Nuxeo, Alation, Aster Data and Granular.

In Today’s Episode We Discuss:

  • How did Dave make his way into the world of SaaS over 20 years ago? How did seeing the boom and bust of the dot com and 2008 affect Dave’s operating mentality?
  • What were his biggest lessons from being in the Sequoia boardroom when they presented “RIP good time”? How does Dave think about when is the right time to raise? How does Dave advise founders on how much is the right amount to raise? Does Dave agree that if the money is on the table founding teams should take it? Why does Dave believe 99% of companies die?
  • The first step in being acquired by a PE house is “making the book”, what goes into “making the book”? Who is involved? How long does it take? What are the clear differences between a good book and a bad book? How should execs think about making exciting enough go-forward plans for it to be attractive to buyers but also realistic enough that they can hit it in the acquisition process?  
  • How does the selection for who receives the book look? Who decides this? What is the fundamental aim in the distribution of the book to many parties at the same time? What does Dave know now about the world of PE that he wishes he had known at the beginning? IOI’s is the next step, what are they? How do they set up the process from there?
  • How do management meetings with potential PE acquiring firms compare to founders meeting VCs in the early days? How many meetings is normal to have in this process? How long do they last? What does Dave believe is crucial to achieve in these in person meetings? How much of a role does price play in selecting the ultimate acquiror? How much of a role does their brand and reputation play?

60 Second SaaStr:

  1. What does Dave know about the process that he wishes he had known at the beginning?
  2. The biggest misconception about the world of PE and acquisitions?
  3. Burn rate is a function of the personality of the CEO? Agree or disagree? Why?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Dave Kellogg

Brex Co-Founder and CEO Henrique Dubugras will talk about what he's learned building the fastest-growing B2B company. Henrique started his first company at 16 and has now built two successful companies from nothing. Learn what he did differently the second time around and the specific decisions he made to drive growth among B2B companies with Brex.

 

Missed the session? Here’s what Henrique talks about:

  • How Brex grew from a few basic functionalities to a corporation
  • Growing from $0 to $2B in ARR in less than two years.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Henrique Dubugras

Amit Bendov is the Founder and CEO @ Gong.io, the startup that provides you with powerful visibility into your customer conversations with conversation intelligence. To date, Amit has raised $68m in funding for Gong from the likes of Norwest, Battery Ventures, Cisco Investments and Wing Venture Capital just to name a few. As for Amit, prior to founding Gong, Amit was the CEO @ SiSense BI software that enables business users to connect to multiple databases of any size. Before that Amit was the CMO @ Panaya, helping companies that use SAP or Oracle to reduce 80% of their ERP upgrade. Finally before that Amit was the Founder & CEO @ SparkThis, an outsourced marketing and sales service for cloud companies.

In Today’s Episode We Discuss:

  • How Amit made his way into the world of SaaS and came to found Gong, the leader in conversational intelligence driving deal conversion and rep success?
  • How does Amit approach the process of idea validation? What can founders do to make sure their idea is a hit before they start work on it? How many customer conversations should they have? What questions are crucial to ask? What are the answers they want to hear? What is enough proof that there is a ready and willing customer base for this idea?  
  • With many products starting as free, how does Amit think about when is the right time to start charging for your product? What does Amit think about the differing variable price mechanisms that one can choose? How does one have a variable pricing mechanism without disincentivizing users to use the product? What does Amit advise founders should charge in the early days? Should they leave money on the table?
  • How does Amit think about monthly/vs annual deals? What are the core benefits and drawbacks of each? How important is it that multi-year deals are paid upfront? What must you account for with regards to multi-year deals? How do you know when you have the right pricing mechanism in place from the sales cycles of the reps?

60 Second SaaStr:

  1. What does Amit know now that he wishes he had known in the beginning?
  2. The hardest role to hire for today?
  3. The hardest element of Amit’s role as CEO of Gong?
  4. SDR is the most important function in the sales org, agree or not and why?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Amit Bendov

Join Molly Ford, Salesforce Global Equality Programs Senior Director, and Leyla Seka, Salesforce VP of Mobile for actionable advice they have applied on their own journey. Here are their lessons learned on driving change in gender equality, equal pay and racial equality within Salesforce.

Missed the session? Here’s what Molly and Leyla talk about:

  • Building a community of allies and allyship
  • How to drive equality
  • What you can be doing as an employee to help drive the culture you want

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Molly Ford

Leyla Seka

 

Parker Conrad is the Founder & CEO @ Rippling, the startup that gives you back your time from payroll to employee computers, Rippling makes it unbelievably easy to manage your company’s HR and IT - in one system. To date Parker has raised over $59m in funding from some of the best in the business including Mamoon @ Kleiner Perkins, Garry Tan @ Initialized, Justin Kan, SV Angel and Y Combinator, just to name a few. As for Parker, prior to founding Rippling, he was the Founder & CEO @ Zenefits, the startup he built from $0 to $60m in ARR in just 3 years. Before that he co-founded Sigfig where he grew assets on the platform to over $35Bn across 500k users.

In Today’s Episode We Discuss:

  • How Parker made his way into the world of startups and SaaS, came to found Zenefits and what was that a-ha moment for the founding of his most recent company, Rippling?
  • What does Parker do with regards to operational scaling that is unconventional but works? Why does Parker believe it is fundamentally better to wait for as long as possible before hiring customer support? Why should engineers also be doing customer support?  
  • Why should your engineers be heavily involved in the customer support hiring process? What are the benefits of this? How can one prevent their customer support team from being a wall of protection for the product and eng team? How can you ensure seamless collaboration and communication flow between product and customer support?
  • Stripe last week recently announced their 5th office would be… “remote”, so how does Parker fell about the building of remote teams? What are the most important things when establishing your first remote team? What do you look for in those hires? What can be done to ensure a greater feeling of community and closeness despite the distance? What have been some of the biggest challenges for Parker in building out the remote team?
  • Parker has been a CEO with 3 different companies now and so how has he seen his style and approach change over the years? What has Parker found the hardest to get good at? When advising founders on fundraising, what advice does he give? How can founders know when is the right time to raise? How should they look to build relationships with investors between raises?

60 Second SaaStr:

  1. What does Parker know now that he wishes he had known in the beginning?
  2. What one thing would Parker like to change about tech and Silicon Valley?
  3. Biggest mentor and what has Parker learned from them?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Parker Conrad

Join Logikcull's CEO and Co-Founder Andy Wilson as he takes you through the mistakes made going from $0 to $10M in 19 months.

 

Missed the session? Here’s what Andy talks about:

  • Selling the way your customers want to buy.
  • What you need to know about hiring, firing, advisors, and culture
  • Why SaaS is your business model, not your mission.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Andy Wilson

Andrew Filev is the Founder & CEO @ Wrike, the cloud based collaboration and project management software that scales across teams in any business. In Dec 2008, Vista Equity Partners acquired a majority stake in Wrike for a deal reportedly valuing the company at $800m. Before this transaction, Andrew had raised over $45m in funding from the likes of Rory @ Scale and Bain Capital Ventures just to name a few. As for Andrew, he started his first software development company at the age of 18 and has been running Wrike for the last 13 years alongside advisory roles with both Ditto and Appulate.  

In Today’s Episode We Discuss:

  • How Andrew made his way into the world of SaaS from his starting his first software business at the age of just 18 and how that led to his founding of Wrike?
  • How does Andrew advise founders on the question of whether to start in enterprise or SMB? What are the benefits of starting in SMB? How does the founder know when is the right time to start moving to enterprise? What are those leading indicators? How does the product and what you invest in proactively need to change as you move into enterprise?     
  • Andrew has been the CEO for the last 13 years, how has the role of CEO changed over those years? What has been the most challenging phase? If the CEO is the guardian of the culture, what does a great guardian look like? What 3 elements does Andrew focus almost exclusively on today within his role as CEO?    
  • What does Andrew think are the major breaking points in the scaling of companies? Where does culture begin to breakdown? What can be done to mitigate this? How does Andrew think about using employee satisfaction surveys internally? How can one accurately determine the strength of your manager set?

Andrew’s 60 Second SaaStr:

  1. What does Andrew know now that he wishes he had known at the beginning?
  2. No man’s land in SaaS pricing, does it exist?
  3. Sales rep productivity, what is good to Andrew?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Andrew Filev

Duo Security Co-Founder and CEO Dug Song and PagerDuty CEO Jennifer Tejada discuss building, enabling, and leading great teams through 10K+ customers, $100M+ ARR, $1B+ valuation and beyond - all while earning 4.5+ Glassdoor company ratings and 98%+ CEO approvals from 500+ total employees!

 

Duo Security is a cloud-based provider of unified access security and multifactor authentication was acquired by Cisco for $2.35 billion in October 2018. PagerDuty is a leading digital operations management platform for organizations announced new financing in September 2018 at a $1.3 billion valuation.

 

Missed the session? Here’s what Jennifer and Dug talk about:

  • When is the right time to raise money?
  • How can you better manage the board?
  • Should you worry about competitors?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Jennifer Tejada

Dug Song

Godard Abel is the Founder & CEO @ G2, the company helping millions of business make better product buying decisions every month. To date, Godard has raised over $100m in funding with G2 from the likes of Accel, IVP, High Alpha, Pritzker Group and Chicago Ventures just to name a few. As for Godard, he founded his first business, BigMachines, in 2000, a business he scaled to $50m in revenue and over 300 people up until it’s acquisition to Oracle 11 years later for $400m. Godard then became CEO @ Steelbrick where he took them from 5 to 200 employees and increased bookings by 37x in 7 quarters. Steelbrick was ultimately acquired by Salesforce where he spent a year and a half before starting G2.  

In Today’s Episode We Discuss:

  • How did Godard make his way into the world of SaaS over 20 years ago? What was the a-ha moment for the founding of G2 for Godard?
  • Having been a Founder through the bust of 2000, how did seeing that macro environment impact his operating mentality today? What did it teach him about capital efficiency and investing ahead of time? Taking the team from 70 to 20, what were his lessons on the right way to let someone go? Where do many people get it wrong today?     
  • Why does Godard advocate for working with people that you have worked with before? How can you find the zone of genius for the people that you work with? How does Godard set a culture of ambition and determination around goals but also prevent dejection if the goals are not hit? How often should rep quota be hit? Why is that the right ratio?    
  • Where does Godard believe that things really start to break down in the scaling of an organisation? What can you do to get ahead of those moments and minimise their impact? How many direct reports does Godard believe is the optimal and then the maximum for a manager to have? How have his thoughts on this changed over time?

Godard’s 60 Second SaaStr:

  1. What would Godard like to change in the world of SaaS today?
  2. What does Godard know now that he wishes he had known at the beginning?
  3. If an investor can provide one value, what would it be and why?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

 

Jason Lemkin

Harry Stebbings

SaaStr

Godard Abel

 

Dave Kellogg is CEO of Host Analytics and prolific blogger. Join him as he takes you through lessons learned from Host Analytics on the top questions every SaaS CEO wrestles with. Dave was CEO of Host Analytics from 2012 to 2018 where he quintupled ARR while halving customer acquisition costs in a highly competitive market, ultimately selling the company in a private equity transaction.

 

Missed the session? Here’s what Dave talks about:

  • When is the right time to raise money?
  • How can you better manage the board?
  • Should you worry about competitors?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Dave Kellogg

Jason Reichl is the Founder & CEO @ GoNimbly, the first SaaS consultancy to focus on revenue operations. Currently growing 100% year over year, working with companies to un-silo their operations and create one strategic revenue ops team to support their Go To Market strategy. In the past, Go Nimbly has helped companies like Zendesk, Twilio, PagerDuty and Coursera to achieve alignment and increase revenue by 26%. As for Jason, prior to co-founding GoNimbly, he was Director of Product Management @ TradeShift and before that was VP of Product Management @ Lanetix.  

In Today’s Episode We Discuss:

  • How Jason made his way from Director of Product Management at Tradeshift to changing the way we think about scaling revenue operations with GoNimbly?
  • Why does Jason believe that we have to remote handoffs between go to market teams? Why are they so damaging? How does Jason believe SaaS companies can use a “swarming” effect to create the best buyer experience for their customer? What does this involve? How does this change the type of metrics that we track?
  • Why does Jason believe that your North Star has to be revenue in the go to market teams? Why does Jason also believe that it is damaging to have the same North Star across the entire company? How should North Star’s be segregated between GTM teams and biz ops teams? What are the mistakes many companies make when setting their internal North Stars?
  • Why does Jason believe that alignment is a dirty word? Why is alignment actually a negative for the customer experience? What does Jason view as vanity metrics? If one has vanity metrics in place, what does Jason recommend as to keeping them or phasing them out?

60 Second SaaStr:

  1. What does Jason know now that he wishes he had known in the beginning?
  2. How does Jason feel about multi-year deals?
  3. How does Jason feel about channel/partner sellers?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

We live in a Shark Tank world: competition is fierce, talent is better than ever, and we’re all striving to come out on top. CEOs everywhere are seeking to innovate, but 81% say their teams are not equipped to meet the challenges needed to compete in today’s marketplace.

 

Innovation is about empathy with your customers. It's all about customer obsession! In this session, Sandy Carter, AWS Vice President will hone your superpower - not of customer focus, or customer driven, but customer obsessed.

 

 

Missed the session? Here’s what Sandy talks about:

  • How to start with success and think backwards
  • Think about how to present a feature or product before you start building.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Sandy Carter

Manny Medina is the Founder & CEO @ Outreach, the market leading sales engagement platform that turns your team into a revenue driving machine. To date, Manny has raised over $114m in funding from some great people including friends of the show in the form of Alex Clayton @ Spark, Mayfield, Trinity Ventures and DFJ Growth, just to name a few. Prior to founding Outreach, Manny spent 7 years with Microsoft where he ran the Latin America and Canada business development group for Microsoft’s emerging mobile division, representing $50M of yearly revenue. Befofe that Manny was a Senior Product Manager @ Amazon where he engineered the compensation system for Amazon Associates and Web-Services which accounts for 15% of Amazon's traffic.

In Today’s Episode We Discuss:

  • How Manny made his way to found the leader in sales engagement from product management at Amazon and Business Development @ Microsoft?
  • How does Manny fundamentally approach managing top of funnel? What are the 2 big dangers of not managing it aggressively? What can be done to ensure not only full but high quality top of funnel?
  • Why does Manny believe it is so important to track pipeline coverage as one of your core metrics? What does good look like when it comes to pipeline coverage? How does this change if you are creating vs in an existing market? How does Manny think about specialisation within the sales function? Why are SDR’s 99% of the time not able to carry leads to completion?
  • How does Manny think about quota construction today? Does Manny err on the side of setting high to be ambitious or setting low to increase confidence? How can managers really empower their reps to be aggressive in hitting their quota and exceeding it? How does Manny think about resource allocation on the individual rep level? What is sufficient? What is excessive?
  • Does Manny believe that the founder should always be responsible for selling their product at one moment in time? How did Manny sell the first $1m in ARR simply through walking the streets of SOMA and selling door-to-door? What were his biggest lessons from doing this?  Why does Manny believe that you should not have a VP before $5m?

60 Second SaaStr:

  1. What does Manny know now that he wishes he had known in the beginning?
  2. What does the future of sales prospecting look like to Manny?
  3. What would Manny like to change about the world of SaaS today?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Manny Medina

Join Glitch CEO Anil Dash and Twilio CEO Jeff Lawson for a discussion about the ethical implications of technology in today’s society. Jeff and Anil discuss how social media and AI are changing the way we think about the impact of technology on society as well as the responsibility of tech leaders for this impact.

 

Missed the session? Here’s what Jeff talks about:

  • How taking no stance as a business leader today, is taking a stance
  • How to set concrete numbers for diversity goals
  • The impact of corporate culture on employee happiness

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Jeff Lawson

Anil Dash

 

 

 

Alexandr Wang is the Founder & CEO @ Scale, the startup providing high quality training and validation data for AI applications. To date, Alexandr has raised over $23m with Scale from some of the best in the business including Index, Accel, Y Combinator, Dropbox’s Drew Houston, Justin Kan, Thumbtack’s Jonathan Swanson and more. Prior to founding Scale, Alexandr was a Tech Lead at Quora, directly responsible for all speed projects and before that a software engineer at Addepar responsible for building and maintaining financial models.

In Today’s Episode We Discuss:

  • How did Alex make his way into the world of SaaS and come to found Scale? What were some of his biggest takeaways from seeing the first hand scaling of Quora and Addepar?
  • Why does Alex take the contrarian view that “TAM in the traditional sense barely matter”? What two characteristics of the market should founders really look to examine? How does Alex approach the element of market sizing? Does he prefer top down or bottoms up and why?
  • Why does Alex believe that you must invest in customer success before you think you need it? What were the benefits for Alex of investing early in customer success? Why does CS over sales ultimately drive the growth of your company? How does one know when is the right time to hire their first in customer success? What is the ideal profile of this candidate?
  • How does Alex think about the integration of customer success and product teams? Why is it crucial from the product perspective that founders pick their first customers well? How can your customers drive your product decisions? How can one ensure to be customer informed and not customer driven?     
  • Why does Alex believe that in the early days it is not important to focus on the size of the deals you are signing? What should founders be focusing on with these early customers instead? When is the right time to flip the switch and opt for value extraction as a more primary objective? How does Alex respond to the fact that VCs often look at these first customer deals as an indication of the size of the pain point you are solving?  

60 Second SaaStr:

  1. What does Alex know now that he wishes he had known in the beginning?
  2. What does Alex believe is the hardest role to hire for today?
  3. Who does Alex think is crushing it in the world of SaaS today?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Alexandr Wang

Leela Srinivasan is the CMO of SurveyMonkey. Join her as she takes you through her seven tips for using customer feedback and building rabid fans. Consistently ramping your ARR is a whole lot harder if your customers don’t stick around. In an age where earning customer loyalty and trust is harder than ever, the road to lifetime value is paved with customer feedback. If you take the time to listen, understand and act on what your customers are thinking and feeling, you’ll create an army of advocates and drive topline revenue growth for good measure.

 

Missed the session? Here’s what Leela talks about:

  • How to create an army of advocates
  • How to drive topline revenue growth
  • Real world examples from businesses that are listening and acting on customer feedback every day.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Leela Srinivasan

 

Stephen Burton is VP of Smarketing at Harness, the industry’s first continuous delivery as a service platform. To date, Harness has raised $20m in funding from the wonderful Matt Murphy @ Menlo Ventures and BIG Labs. Prior to Harness, Stephen was VP of Marketing at Glassdoor, managing a team of 52 in product marketing, helping grow B2B revenue from $19m to $90m in just 2 years, leading to their $1.2Bn acquisition. Before Glassdoor, Stephen was VP of Product Marketing at AppDynamics where he helped grow B2B revenue from $0 to $100m in a staggering 3 year period, resulting in their $3.9Bn acquisition by Cisco.

In Today’s Episode We Discuss:

  • How Steve made his way into the world of SaaS and came to be VP of marketing at 2 of the larger B2B exits of the last decade in AppDynamics and Glassdoor? What were Steve’s biggest takeaways from seeing the hyper-scaling at AppDynamics?
  • Steve has previously said, “sales and marketing must be one team”. Why does he believe this is so important? What can leaders do to turn this into reality? What works? Where has Steve seen many make mistakes? Where does Steve find common points of tension between sales and marketing? WHat are the 3 elements that marketing comp should be tied and aligned to?
  • What does Steve mean when he says, “marketers need to embrace the developer first mindset”? What does this mean for the processes used by marketing teams? Speaking of developer-first, how can startups compete in a war for talent against FB and Google? How can they integrate autonomy into their hiring process as a core advantage?     
  • For Steve, what does devops really mean? What does Steve believe is the right culture for devops teams? Does it differ from traditional dev teams? How can a CEO determine when is the right time to fundamentally invest in devops? What are the required steps to make devops teams as successful as possible?

60 Second SaaStr:

  1. What does Steve know now that she wishes she had known at the beginning?
  2. When is the right time to pour fuel on the company fire?
  3. The playbook? Is there one? Dangers? Copyability?
  4. What would Steve most like to change in the world of SaaS?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Stephen Burton

 

Mikkel Svane is the CEO of Zendesk and author of "Startupland". Join him as he takes you through his lessons taking Zendesk beyond a billion in ARR. Mikkel founded Zendesk in Copenhagen, Denmark in 2007 before moving the company to San Francisco in 2009.

Missed the session? Here’s what Mikkel talks about:

  • The future of the cloud
  • The rise of the public cloud and re-platforming of the tech stack
  • How business applications are sold and delivered leveraging SaaS

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Mikkel Svane

Karen Peacock is COO of Intercom, one of the fastest growing SaaS businesses of all time. She has led businesses of all sizes through massive growth.  Listen to her top 5 lessons learned building and scaling SaaS businesses from $1M to $500M in ARR including expanding to serve upmarket customers, moving from product to platform, and hiring to drive breakthrough customer experiences and business growth.

Missed the session? Here’s what Karen talks about:

  • How should you expand your market?
  • How to move upmarket
  • The steps to building a product and creating an end to end experience

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Karen Peacock

Ben Braverman is the CRO @ Flexport, one of the world’s fastest growing startups combining technology, infrastructure and expertise, to build the operating system for global trade. To date they have $1.35Bn in funding from some of the biggest and best in the business including Softbank’s Vision Fund, Founders Fund, DST, Susa Ventures and Y Combinator, just to name a few. As for Ben, he spearheads global sales and go to market teams. Prior to Flexport, Ben helped drive two high-growth companies to successful acquisitions: URX (acquired by Pinterest) and Heyzap (acquired by Fyber).

In Today’s Episode We Discuss:

  • How Ben made his way into the world of startups and came to be CRO of one of the world’s fastest growing startups in the form of Flexport?
  • Why does Ben fundamentally disagree with the specialisation of roles within SaaS companies? What does he believes this does to the customer journey and relationship? How should one thing about role segmentation and allocation of accounts with this in mind? Where does Ben see many people going wrong here?
  • Why does Ben believe it is “total horseshit to say the best sellers don’t make the best managers”? What must founders try and figure out before hiring their sales leader? What are the leading indicators that suggest a sales rep has the ability to be a sales manager? How does Ben determine between a stretch VP and a stretch too far?   
  • What does Ben mean when he says, “there are 3 distinct buckets of sales management”? What are they and what is their relationship between one another? Why does Ben believe one does not need sales management in the early days? What is the best way to train reps and determine payback period fast? Why does Ben believe sales ops is the most underappreciated role in the valley?

60 Second SaaStr:

  1. What does Ben know now that he wishes she had known at the beginning?
  2. What is the optimal relationship between CRO and CEO?
  3. What does Ben believe in SaaS that most around his disbelieve?

 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Ben Braverman

Mark Roberge is a senior lecturer with Harvard Business School, former CRO of Hubspot and author of the bestseller "The Sales Acceleration Formula". Join him as he takes you through his step by step guide to revenue growth.

 

Missed the session? Here’s what Mark talks about:

  • An in-depth guide to driving revenue growth by company stage
  • When to scale and how fast
  • Product market fit, go-to market fit during the experiment stages

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Mark Roberge

Leyla Seka is the executive vice president of the Salesforce Mobile platform experience. Over Leyla’s incredible 11 year journey with Salesforce she has seen the team scale from 1,800 to over 40,000 and revenue scale from $500m to over $16Bn. In Leyla’s role today, she leads the charge on extending the power of Salesforce with a full portfolio of mobile apps, and is responsible for driving product, go-to-market and other key programs around Salesforce’s mobile offerings. Prior to her current role, Leyla was executive vice president of the Salesforce AppExchange, where she launched a refreshed AppExchange storefront, a new partner program, and built an entire AppExchange-focused team, resulting in more than 4,000 solutions, installed nearly 6 million times. Beyond her day-to-day role, Leyla is also the executive sponsor of BOLDforce, Salesforce’s organization for expanding and empowering the black community at Salesforce.

In Today’s Episode We Discuss:

  • How Leyla made her way into the world of SaaS with Salesforce when it had 1,800 people and $500m in revenue?
  • What were Leyla’s biggest learnings on people and business model through seeing the first hand hyper-scaling of Salesforce from $500m to $16Bn? How did Leyla evolve and scale as a leader herself in those 11 years? What advice does Leyla give to young people considering whether to found a startup, join a startup or join a hyper-growth company?
  • Where do things start to break in the scaling of SaaS companies? What needs to be put in place to prepare for hyper-scale? What are the commonalities of where many founders go wrong in the scaling process?  
  • What does Leyla mean when she says, “growing up in product, you have to lead through influence”? How does Leyla think this influence can be created and maintained? How does Leyla think about the balance between effective influence and excessive influence?  
  • Why does Leyla believe that, “you can teach skills but you cannot teach empathy”? What have been her learnings from scaling teams when it comes to hiring and detecting candidates with true empathy? What can one do to nurture that empathy in the culture of the company?

60 Second SaaStr:

  1. What does Leyla know now that she wishes she had known at the beginning?
  2. What is the hardest element of Leyla’s role at Salesforce today?
  3. What does Leyla believe in SaaS that most around her disbelieve?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Leyla Seka

At Atlassian, openness is core to everything the company does: employees can access most information on Confluence; "open company, no bullshit" is one of the company’s five values. But it can be risky. Atlassians knew the company was going public four months before it filed. The entire company was told about Atlassian selling its chat products Stride and Hipchat to its largest competitor in the space, Slack, four days before the news went out. Some would say that that level of openness is unnecessary, but Atlassian believes that trust and honesty are essential to maintaining the culture its worked so hard to build.

 

Missed the session? Here’s what Jay talks about:

  • What is driving growth in the cloud?
  • Does collaboration help founders drive growth forward?
  • How do you scale an open culture?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr