The Remote Show on Smash Notes

The Remote Show podcast.

December 28, 2019

The Remote Show is an interview style podcast devoted to all things remote work, entrepreneurship, business and much more. We dive into our guest's personal journey, discuss tips, tools, management concepts and much more in order to help today's remote worker be more productive and fulfilled in work and in life.

Recently updated notes

 Kate is a career coach and founder of The Remote Nomad. She has been profiled in a number of large publications for her expertise in all things remote work, and she helps clients around the world find remote jobs and excel in their careers.

In light of the current environment, we wanted to create a more interactive show where we talked about finding a remote job and answered questions from our listeners directly.

You'll notice that the audio sounds a bit different. Like many out there, we've had to adapt and were unable to use the studio setting for our recording  session. Hopefully this session was helpful for listeners out there! I know I learned a lot from Kate and we hope you did too. 

Please check out the Remote Nomad  from more information on Kate and to purchase one of her courses. She also has a free ebook for our listeners, find that here. 

More to come in this format! We'd love to hear your thoughts on how we can improve the show and be as helpful as possible. Send us an email at -- we'd love to hear from you!


Matt Hollingsworth (00:00:07):

Hello, everyone. My name is Matt Hollingsworth and welcome to another episode of The Remote Show where we discuss everything to do with remote work with the people who know it best. Thanks so much for listening. The Remote Show is brought to you by We Work Remotely, the largest community of remote workers in the world. With over 220,000 unique users per month, We Work Remotely is the most effective way to hire.

Matt Hollingsworth (00:00:25):

Welcome, everybody. We're going to get started here in a few seconds. I'm just going to allow people to get into the room here. So just as a quick introduction, again, we're going to give this a few seconds here for people to come on board. Participants are already climbing, which is awesome to see. Hopefully, that number keeps going up. So I'm going to kick this off. So this is technically part of The Remote Show Podcast. So welcome everybody to Remote Show Live. This is the first time we've ever actually done this. Hopefully, this is valuable. Again, we're new to this structure so we're figuring this out as we go. There's some chats in there as well. That's awesome.

Matt Hollingsworth (00:01:14):

I'm going to do a quick introduction to my guest today, Kate Smith. Some of you have probably seen Kate before or know of Kate already. She is a remote coach. She's the founder of The Remote Nomad. She's been on a number of high profile, different publications. She's been on CNN and Glassdoor. Kate, you can fill me in if I've missed any of those. But she's very prominent, a very knowledgeable person in the remote workspace so really happy to have her on. Kate, welcome to the podcast.

Kate Smith (00:01:47):

Thank you for having me. I'm excited to be here today and just share a bunch of knowledge and information from what I know and from my experience and what's been working with my clients with everybody today.

Matt Hollingsworth (00:01:58):

Yeah. We're super excited about this and we're happy to have you on. I just wanted to start by talking a little bit about the context that we're doing this. I think, it's important for us all to recognize that this is a pretty unique time for everybody. I know that in a lot of circumstances, this is a very uncertain time, I know people have maybe lost their jobs or looking for work in a different space. I think we have all been there before in that level of uncertainty. I just wanted to start by saying that and I think we are all in this together. This is the reason why we're doing this, is to help people that are looking for work. That is the reason we're doing this. Again, we're happy that you all are here to share that with us.

Matt Hollingsworth (00:02:50):

Kate, I think, well, actually, before we get into the questions here. Because we don't necessarily know the stages of everybody's remote work experience where people are at generally speaking with their remote work, their journey and if they are, for example, if they just lost their job, for example, or looking from a standing start how to get a remote job. If they're already remote workers and potentially looking for a career change in a space that's still remote and just a career change in general, the latterly up, whatever stage of their own works, that journey they're in. We would like to know that just because it will give us a sense of how to be the most helpful we can possibly be here. This is the goal.

Matt Hollingsworth (00:03:35):

Obviously, this is a free webinar that we're doing to help people find work and we want to be as helpful as we possibly can. So if you could put that in the ... Actually what I'm going to do here ... This is so cool, the chat. I'm going to put that in the polling here a couple of questions, and hopefully we can get a sense of where people are out with it and be as helpful as we can. I'm going to launch this poll. Again, this is the first time I've ever done this, so bear with me if this doesn't go well here. So I'm going to just launch this.

Kate Smith (00:04:04):

So if you guys can just let us know if you have lost your job due to COVID, if you're looking for remote work, just kind of what your situation is, so that we can have a better idea and make sure that we tailor the discussion today to where you guys are at.

Matt Hollingsworth (00:04:22):

All right. I've just put that poll out. It looks like the vast majority of you are looking for remote work. Now, that makes sense. I'll just change up the question here, because I think that's a pretty obvious one. So if anybody's interested, everybody ... Pretty much everybody here is looking for remote work. I don't know what everybody else is doing here. If you're not looking for a remote job, if you're just looking to ...

Kate Smith (00:04:45):

Kill some time during quarantine.

Matt Hollingsworth (00:04:48):

... kill some time in which we're also ... Hopefully, we can help with that as well. So I'm going to end this one and I'm actually going to put up this next one here as well. Okay, when we're going to ... So we appreciate putting in the chat there what your experiences. We'll kind of scroll through, hopefully, we can kind of pick these things up as we go. But anything you want to put in there is helpful. I'm going to put out a different poll here as well. Okay. The next poll here. Go ahead, Kate.

Kate Smith (00:05:18):

Could you do one and see if anybody has recently lost their job. I think I'd be curious to see if anyone's been impacted in that capacity.

Matt Hollingsworth (00:05:26):

Okay, great. The poll is out there now. The first poll that I [inaudible 00:05:31]. This next poll has, "Have you worked remotely before?" In the chat, if you could just say if you're looking for or if you just lost your job, that will be helpful. All right. It looks like here, "Have you worked remotely before?" The answer is 65% of you have worked remotely before and 36% haven't. So that's a pretty ... That's kind of what I was expecting. To a large extent, I think that's a good place to start.

Matt Hollingsworth (00:06:08):

Well, why don't we start this off with actually with just the, "You haven't worked remotely before." And this is going to be, the way that we're going to do this folks is we're just going to, I'm going to ask questions to Kate and then I might be able to add some value to part of the question or I might able to chime in as well. But my job here is to really pick the brain of Kate, hopefully, add something a little bit valuable myself.

Matt Hollingsworth (00:06:30):

So Kate, in the context of somebody who potentially has just lost their job and they haven't worked remotely before, maybe they have worked in the tech space, maybe they haven't. I'm sure it's a pretty intimidating thing to go into this. Not even knowing where to start. What would be step one for somebody out there that is feeling that they really don't know where to start with this, they maybe are looking for a career change and they just are feeling overwhelmed. What's step one, do you think?

Kate Smith (00:07:02):

I just wanted to share with everybody that I've been there. So my personal journey of working remotely, I've been working remotely now for over five years now, I had a corporate job in advertising. It was my dream job at the time. You know, as time went on, a couple years in corporate, I realized, this isn't for me, I like to travel too much. Two weeks vacation is not going to cut it. I didn't like staying at a cubicle all day. I started saving up to quit my job and I actually ended up getting laid off. So for those of you that have been laid off, that is actually what kick started my journey.

Kate Smith (00:07:35):

I remember at the time, I was working with a life coach and she's like, "How are you feeling? You know, you've just been laid off." I'm like, "I'm so excited. There's so much ... I can do what I want to do now." At that time, I didn't even know remote work was a thing and ironically enough, I was working remotely right after university for a few months. I had this job that I was doing at university, doing it from a distance. But anyways, what I just want to share with you guys is that you can look at this in two ways, like "Can I ..." Is it fine if I swear sometimes when I get into things? Slips out of it?

Matt Hollingsworth (00:08:07):

Sure. I think we're okay.

Kate Smith (00:08:08):

Okay. You can look at it two ways, you can kind of look at it as this, "Woe is me," and fall into this victim mode and just kind of feel defeated for the whole thing. Or you can see it as an opportunity and possibility and potential. For me, I mean, obviously, I learned the hard way how to land a remote job and I did land a remote job and I had that job for a few years, working remotely, traveling the world before I started my own business. But I just want to let you guys know for those of you that have been laid off that, yes, it sucks. Yes, times may be tough, but you get to choose what you create and how you come out of this.

Kate Smith (00:08:48):

I know it's tough because when I went remote, I put all of my savings down to join a program and book a one way ticket to Prague. I think it was like $5,000 at the time, five or $6,000. Even at that time, I was hoping to land a remote job. Didn't really know what I was doing. I even brought on my carry-on, [inaudible 00:09:11] on my carry-on to the Prague, I brought a bag of food because I really ... Money was tight. I was like, "Okay, I got one month to figure this out. Get a remote job." I'm not really sure how I'm going to feed myself so just in case, I'm going to bring some food. And it worked out.

Kate Smith (00:09:26):

But I just want to let you guys know that with the right process, with the right strategy and knowing where to look and how to find these opportunities, it's there. It may be challenging, it may be tough, it really comes down to what are you willing to do to make it a reality. For me, I was willing to do pretty much anything within reason. And that led to my journey. So if anything, I just want to convey to everybody that just because this situation sucks right now, doesn't mean the opportunities aren't there. Even when we look at the space in the industry, a lot of people are wondering, "Are there remote jobs out there? Are people even hiring."

Kate Smith (00:10:07):

A big thing that I predict that we'll see in the next year or two is that a lot of companies have now been forced to operate remotely and they're going to start to realize, "Shit. This is a more efficient, effective, better model to business. It saves us a shit ton of money. We don't have to pay for all this overhead." And a lot of companies now that aren't even remote are going to start shifting to that model, which is a beautiful blessing in this whole scenario. The founder of Twitter even mentioned recently that he's going to shift his whole company to a remote model. That's just the start. There are so many companies that are going to make that transition. So there's just so much opportunity and possibility here for everybody. I just want to leave you with that.

Matt Hollingsworth (00:10:53):

Yeah. Totally. It's a great message. I think it's also important to know. I'm going to kind of answer my own question and I apologize, I do that sometimes with these kinds of things. I think it's also important for people to know, too, if you're looking to go remote and you're looking to ... If you're feeling like you're at a standing start, essentially, and you're having to take the first step through becoming a remote worker, oftentimes, you actually ... Whatever field you're in, whatever skills you have, that might be already a part of a remote job. People don't associate necessarily ... If you're in the financial sector, for example, if you're in accounting or if you're even in the medical field, if you're, whatever, all that kind of stuff is actually now and I think will continue to be, to your point, will continue to be the case where you'll be able to ...

Matt Hollingsworth (00:11:43):

There are remote jobs related ... Maybe not exactly what you're doing, but it's related to the skills you have. So it's going to be easy for you to then transition to find that remote job. I do want to mention that, too, as an important thing to note. It doesn't necessarily mean you have to start from scratch. That might be the way you want to do it. For those folks, we'll get into that as well but you don't necessary ... It doesn't need to be the case and there might be an option that's more relevant to whatever you're doing now.

Kate Smith (00:12:08):

Yeah. Just to add on to that, a lot of people have this assumption that what they do can't be remote. Like you said, Matthew, it's the complete ... It's just not true. For example, I used to be a project manager and oftentimes people think, "Well, I can't work remotely as a project manager, I have to meet with clients." Well, there's [inaudible 00:12:28] assume, remote companies have these ways to navigate that. There are over 50 different spaces and industries that operate remotely. They just do their business in a different way, you can do the same job, it's just done in a slightly different way. And sort of what you were saying and leading into what you're saying as well is that you can often take the transferable skills that you have and find a remote role. Even if it's not the exact role, you can pull on those transferable skills to fit into that ideal remote role.

Matt Hollingsworth (00:13:02):

Yeah, yeah. For sure. Also like I said, I think, so for somebody that is looking to start from scratch essentially, it's time for a complete career change. Maybe the wave of job losses we've been seeing has led them to rethink their careers. I mean, kudos to you if you're in that position, I think it's a brave thing to do. It takes a lot of courage to go out and try something new and get into a field that you're normally experienced in. So question to you would be, Kate, how do you start to think about the things you might be good at? How is it just based off of interest, generally speaking, like is the kind of throwing darts at a dartboard, how would you go about starting to look for things that might be interesting for you in a remote context?

Kate Smith (00:13:53):

I think it's first identifying what are my skills and what transferable skills do I have? The way I explain remote work to a lot of people, and it's a bit tricky, is because everyone thinks, "What kind of job can I get as a remote worker?" That would be like me asking people, "What kind of job can I get in the corporate nine to five environment?" It's like holy shit, there's a lot. And it's the same with the remote working world. Those opportunities are there. You know, Matthew, you guys have We Work Remotely. There's a lot of sites out there that post remote only job depending on the industry and role. So what I would do is look at, "Okay, what are those transferable skills? What are my current skills? What kind of role do I want to apply that to?"

Kate Smith (00:14:40):

Maybe not so relative to what you're saying right now, but when I started my journey and I had no idea what I was doing, I started doing a bunch of random stuff to explore what I wanted to do. You know, I was researching, "Okay. Should I become a nutritionist? What does that look like?" I stumbled across the program Remote Year and that's when I was introduced to remote work and I thought, "Okay, I can just do what I'm doing but do that remote." I think it's starting at looking at your transferable skills, looking at currently what you're doing and there is a chance that you can just do the same job remotely.

Kate Smith (00:15:17):

I think a big thing as well that a lot of people underestimate a lot is building your network, tapping into your current network, building that network, building that network. So if you look at it, I saw in the chat here, someone was saying, "You know, for every job that's posted, there's so many candidates. So how am I to stand out?" The reality is, is you've been working your network and growing and nurturing your network over time, you're going to have that ability to find and uncover opportunities and stand out among everyone else.

Kate Smith (00:15:49):

Referrals are a great way to stand out among ... Referrals have a higher hiring rate than other people. Their whole journey is faster. I think they get their journey to getting hired is like four to five times faster than most people. So another big thing is start building that network, LinkedIn. There's so many ways to connect with people in the virtual world. So start tapping into that growing and nurturing your existing network.

Matt Hollingsworth (00:16:17):

The networking piece is really important. For myself, I always assumed or I thought to myself, "You're not really a networking person." I think for people that have that as their starting point, it's really difficult to see themselves in a position of, "Okay, I'm just going to reach out to this person, I'm going to ask them a question. I'm going to maybe see what they do and see if it's interesting to me." It's a good segue, actually, to talk about networking. For somebody that isn't really their thing, doesn't come naturally to them, what's a way to approach networking and maybe reaching out to people that doesn't come across as spammy or annoying. Is there ways or process you have or thoughts you have to that?

Kate Smith (00:16:57):

I think biggest thing when it comes to networking is your mindset and how you perceive it. A lot of people will think of networking as, "I want a job and I'm going to try to connect with this person to get a job." That's not what networking is and that's not what it should be for. Networking is a long term strategy and the way that I approach it is I want to simply meet, I'm curious to meet similar like-minded people. And that's it. Have a conversation, be a value to them. Don't just be like a leech or a suck. People don't like that, to be spammy.

Kate Smith (00:17:33):

But just start a conversation. Just how you would connect with people like, "Hey, you seem really interesting." "Wow, I saw that you're doing that. That's really cool." Or you know, "I've been following your content on LinkedIn. I love that you said this." Even just as much as insightful comments on ... Follow someone on LinkedIn, leave insightful comments on their posts like, "I read your recent article on LinkedIn. I really liked this and that." They're just like, "Hey, I care." I also just want to mention here, too, that LinkedIn is a huge networking opportunity. I think people underestimate the opportunity.

Kate Smith (00:18:08):

I have a client that I'm working with recently and he started doing that approach, leaving insightful comments, following people, connecting with people. And he had the CEO of Wired respond to him, and he's like, "Holy shit, how did that even happen?" And it's because you have Instagram, Facebook. We have a lot of saturated places online but LinkedIn isn't and it's a huge opportunity. It's set up for professional networking so there's a huge opportunity to connect with people. But again, I think the biggest thing to consider is simply look at it as connecting with interesting like-minded people, get curious about people, "Hey, what you're doing seems really cool," and ask them questions. And don't approach it with this mindset and mentality of like, "I want a job. How can I use you to get this job?"

Matt Hollingsworth (00:18:55):

Yeah. Totally. I would also like to mention too, LinkedIn is a great obviously resource. I think Twitter is another one as well where it's super important. Again, for people that don't see themselves in that niche of, "I'm going to use social media to my benefit. I'm going to grow my network." One thing that I've found to be helpful and I've seen successful in the past is just, like you said, leaving insightful comments, asking questions to people, follow people that you think are interesting. Because oftentimes, that in itself is enough to justify following them in the first place.

Matt Hollingsworth (00:19:27):

Then also just comment on their tweets, try to engage with them in some way. That might not be the direct reason why you get a job but at least ... Because it's such an exponential thing, people will see your name, maybe a friend of theirs or whatever will see your name because you were on Twitter and you interacted with them in some way. As well as LinkedIn, I think Twitter is really an important thing to keep in mind.

Kate Smith (00:19:55):

Another thing just to add to that as well that a lot of people need to realize is that it's the 21st century. Everything is online. And if you want to stand out among the competition and give yourself an edge, so to say, building that personal brand is really important. It can be as simple as, as you read articles in your industry and space, to share it on LinkedIn and write your thoughts or comments, "I just read this article, here's a few takeaways I had. I think it's really interesting." As you continue to post, people are going to start noticing and seeing your name. It's like that omnipresence.

Kate Smith (00:20:30):

Another little trick, too, is Google yourself. So many people don't Google themselves. It's like when you're applying to these jobs, the recruiters will Google you. It's just a natural thing. You're Googling the company, you're learning about them, they're going to do the same to you. So I encourage you all, just as you're going on these social platforms and as these recruiters are going to be creeping you online, clean up your social profiles. If you're on Twitter, if you're on LinkedIn, make sure it's professional and clean and something that you would want an employer to see. Google yourself. If you have Facebook, if it's very personal, just tighten up those security settings and just recognize that as things are online, networking goes online, it's part of building this personal brand, so to say, to give yourself an edge.

Matt Hollingsworth (00:21:21):

Yeah, yeah. Totally. So I'm actually going to just take a step back quickly and just talk about this. I forgot to mention this at the start. So apologies, it's my fault. We're going to do this conversation back and forth for a little bit longer here in probably about 20 or so minutes more, and hopefully this is helpful. Please do keep commenting in the chat to let us know if we're on the right track or not. I would like to mention though, too, we're going to do a Q&A session afterwards. At the end, at about 25 minutes or so, we're going to open up to a Q&A.

Matt Hollingsworth (00:21:50):

If you do want to, leave us a question and that we'll get to and we're going to scan through them when that time comes. Please do leave that in the Q&A section right now or until the end of the thing here so we can get to that question when we can. Just want to mention that quickly. A few things, actually that I've seen here in the chat so far and I think we were going to touch on this piece of it anyways, is just like ... You maybe have some skills, maybe you do meet the qualifications of a job posting that you see online, something's interesting to you. You go on and you apply and all of a sudden you're within one of 500 people that have applied for that position.

Matt Hollingsworth (00:22:30):

Which is a pretty common thing, I think, you know, especially with the junior to mid-level positions, oftentimes, companies that you want to work for will get a lot of people that also want to work for them. Is it the cover letter, is it the resume, is it the structure of it, is there easy nos that you can avoid being that person that people just disregard completely because you didn't do something, didn't do X, Y, or Z? So let's just focus a little bit more on the resume cover letter piece. Kate, if you have any thoughts on that.

Kate Smith (00:22:59):

I feel this is a loaded question and there's so much I could say on this. But if we're going to talk specific to cover letters and resumes, you could be the most talented person, most skilled person in the world. If you don't know how to showcase your skills or connect with the right opportunities in the right way, it doesn't matter. So there is a bit of a skill and an art to understanding how to find opportunities and how to present yourself a value to a company. What I'll just share, which will hopefully be a value of everybody today, and you can take this option today to improve your resume to help you stand out, there are probably ...

Kate Smith (00:23:38):

I'll give you three things, three main things that people usually fail or fall short on their resume. Number one is a lot of people will just focus on their job duties. Like, "I did this, I answered phones, I filed whatever it may be." Instead, you want to make sure you're focusing on your stats, impacts, and achievements. For example, by implementing a new system or process that you implemented, you made whatever process 30% more efficient, something like that. So focusing on those stats, achievements, and impacts, and a lot of people don't do that.

Kate Smith (00:24:14):

The second thing to recognize is that when you're applying to remote jobs, I would say 90 to 95% of those companies are using an applicant tracking system. So an ATS system, I'm not sure if you guys are familiar with that. What it means is that your resume is going to go through a machine before it even gets to a person. It is super important that you tailor your resume based on the job description. An easy way to do this is go through the job description, pull the keywords from that job description and make sure that you put that into your resume and that it's tailored. Be a little cautious if you have an overly graphic designed resume, because sometimes that doesn't go so friendly through the ATS system.

Kate Smith (00:24:56):

What was the third thing? Making sure you tailor your resume with those keywords, making sure that you focus on those stats and achievements. I can't quite remember what the third one was. But a lot of people, what they'll do is they're going to focus on quantity over quality. They're just trying to pump out these resumes. Be very careful where if there's a job description and it says, "We want you to, in addition, create a five minute video about yourself." Don't skip out on that. If you skip out on that, you're going to be an automatic no.

Kate Smith (00:25:29):

Honestly, just give it your all. Give every application 100%. So many people will just try to pump out the resumes and do quantity over quality, but quality will far outweigh quantity every time. Remember, if you're tapping into that personal network as well, that's giving you an additional edge when you're applying to these jobs. Does that help answer your question? Is there anything else that I missed or that you want to add in terms of that?

Matt Hollingsworth (00:25:52):

Yeah. I think that's a good, those are really good points. I think the really important piece that I've seen, because I've seen a few, we've seen few resumes come through and it is clear which ones have spent the time to really understand the job that they're applying for. Which you would be surprised or maybe you wouldn't be surprised to know that a lot of the jobs that, or lot of the job applications we see, clearly, you don't know the company, you don't know what the role is or maybe you saw it and you thought that it was ... We said it's the spray approach of just like hoping something sticks.

Kate Smith (00:26:30):

Okay. Another story, just on that note. A lot of people in their cover letter, they'll write something like, "I see that you operate remotely and I'm super excited. I want to work remotely because I want to travel and have that flexibility." Do not ever, I tell my clients, "Don't ever, ever say you want to work for a remote company because they're remote. Don't even mention it." It's a thing that you know but you don't talk about. To remote employers, that says, "You don't care about us, you just want to work remote." Then similar to what you were saying, Matt, just because there's 1,000 applicants applying to a job doesn't mean they're 1,000 good qualified applicants. A lot of those could just be shit resumes. So keep that in mind as well and don't let that hold you back from applying.

Matt Hollingsworth (00:27:15):

Yeah. And it doesn't need to be ... The other side of this, too, which is I spend way too much in one specific one, because you think that this is the job for you, this is the company for you. I think it's really easy to go down that rabbit hole, too. And then now often when you don't ... And this will lead into this next question here, but when you don't receive a positive response or any response really from the company, that can be really dejecting because you've spent so much time on this one resume and this application and all sudden that's a no go.

Matt Hollingsworth (00:27:45):

So there's a happy medium there and I think it's a really hard thing to really pinpoint. But just acknowledge that spend the time to know the company, know the rule, show that you care and then apply and then move on. Don't put all of your eggs in one basket emotionally, because that's quite easy to do. Then I've had that experience as well. Just try to focus on ... As well, try to focus on the companies that you want to apply for. I think, this potentially is something that not everybody has the luxury to do in some cases.

Matt Hollingsworth (00:28:17):

So if you're looking for a job and you're maybe not as qualified or this is new for you, then maybe you do have to take that all out approach. Let's face it, we all need jobs and that can be the reality for some folks, but I think it shows that you know, if you read a resume and a cover letter that is specific to the company, you can show within your cover letter that you care about the company, that goes a long way. That might not get you the job, but between five candidates, if you're equally qualified as the other people, that will get you a job over those other folks that didn't do that.

Kate Smith (00:28:50):

Yeah. And just to add to that, sometimes your passion about a company and what they're doing can go a lot further than your specific skills. Because you can't teach someone to be passionate and excited about a company, but you can teach them skills. So keep that in mind, too.

Matt Hollingsworth (00:29:05):

Yeah, yeah. Totally. So this is my next question, if you have a job that you really, really want and it's something that you think you'd be really good for, how do you go about applying for that job in a way that that shows initiative, that goes the extra mile, that makes sure that you are the head of the fact in terms of being visible but isn't annoying. Because everybody's had that, I think ... Well, maybe not everybody, but I've seen that happen before where it goes too overboard and you're just wanting to get ahead of the person or get in front of people. It just comes off as spammy a little bit. Is there anything that you have thought about it just to show that you care and then maybe that's it. Do you see what I mean? What I mean is there anything there that you would suggest?

Kate Smith (00:29:49):

I mean, one way that can help ... Well, first of all, follow up with companies after you apply, about a week after, I would say. But make sure the job posting has been closed down. If it says explicitly don't follow up, then don't. Otherwise, it's okay, just send a quick follow up. A good way for a company to get a sense and feeling about who you are without having any pressure to it is setting up informational interviews, which is simply connecting with people at different companies saying like, "Hey, your company sounds really cool. I'd love to learn more about what it's like to work there. Do you mind ..." In that conversation, you can get insights and they would learn more about you and they can give you specific feedback like what do people ... What does your company look for in candidates? What could I do to present myself as stronger?

Kate Smith (00:30:40):

And when somebody is giving you that feedback and advice, they're going to have a vested interest in seeing you succeed. It's just a psychological thing. They're like, "Okay, I gave you advice on how to succeed, now I want you to succeed." So that's something to keep in mind, too. Just keep in mind, this whole journey and process is a lot of learning. Don't just keep doing the same thing over and over when you're applying to jobs and expect. You know, just say you're applying to all these jobs all this all the time and you're not getting any results, try out different things.

Kate Smith (00:31:12):

Maybe you find, "Okay, these type of jobs, I'm not hearing back. These type of jobs, when I follow up, I'm hearing back from them." So try out different strategies and approaches and really look at it with some curiosity and learning. Don't just keep doing the same thing forever. Always try out different things, "Okay, maybe I do this to stand out or that to stand out." Maybe not super relative to remote work, but I remember when I was applying for my internship to study at university, I was meeting with the CEO of the company, and I had to drive four hours from university to the company, met with him and I just casually mentioned it, because he had talked about, you know, small talk.

Kate Smith (00:31:50):

I was like, "You know, it's middle of exams. I just had to drive down or whatever." He's like, "You drove four hours to have this 30-minute conversation, only to drive back in the middle of exams?" And I was like, "Well, yeah." And I didn't think anything of it. I was like, "I want the job. Of course, I would." So there's going to be even opportunities like that that may come up where you can just show that you care. Like don't reschedule an interview, do whatever you can to be on that call and make sure you have good internet, make sure your background's quiet, show that you care. I think showing that you care can go so far.

Matt Hollingsworth (00:32:23):

Yeah. Totally. There's some interesting case studies or things that I've heard. Actually, this is sort of how I got my job in first place, as well. So I'll share a little bit about that. One thing that I found to be really effective and even if you don't get the job, I think people that are hiring really appreciate this way of going about it. In some cases, I've seen ...

Matt Hollingsworth (00:32:48):

Let's say, for example, if you're a designer or if you are a programmer or you're something that you can build something online, what I've seen people do is they'll reach out to a company and say, "Hey, there's this part of your site online that I think I thought could do some redesign. I'm a designer, this is my background. I know that you're busy and this is just something that I wanted to do in my spare time. Here you go. I've redesigned your ..." in sketch or whatever, "I've redesigned this part of your website or this part of your business. Let me know what you think. This is yours. That's totally fine if you don't even use it, but I thought you might appreciate it."

Matt Hollingsworth (00:33:27):

That combination of, I know for myself, would go ... Even if I don't hire the person, even if there's no job opening available, that kind of initiative goes a long way. A second part of that segment, which is like, "What skills do you want to get to be able to do that kind of thing?" If you're starting from scratch, obviously, that's a different question you need to ask yourself, but if you have a skill and you want to showcase that, there are ways to showcase it. That's a really interesting way of going about it. They're like, "Hey, this is what I wanted to do for you, let me know what you think."

Matt Hollingsworth (00:34:04):

My story that I wanted to share with myself was, when I first got ... There was no actual opening for the company that I started working for and that I actually ended up with where I am now. But the owner of the company, I went and had coffee with him just out of the blue, just kind of a random connection, and I didn't know anything about them. We chatted and I got to learn about what he was doing and his company and what we he was promoting as well. And I was like, "That's really cool." Again, I'd been working in banking, hated it a lot, and I wanted to get out and do something different and want to get something in tech, hopefully.

Matt Hollingsworth (00:34:42):

I said to him, and not everybody is in a position to do this, but I told them that I would work for free, "If you could find anything that I could be helpful in doing, I could do that for free for three months. And if after the three months, you don't think that it's valuable, you're not getting anything out of it, then for sure, I'll go a different direction. I'll try something else. And if not, we'll have to talk about that in three months’ time. But if I could be helpful to you in that three months, then let's do that." That's how I got the job. And here I am. It was three years later and here we are. And again, not everybody can do that but it's something to think about.

Kate Smith (00:35:20):

I would challenge that. I would say everybody can. If you're working 40 hours a week, you still have a lot of time outside of that. It's just whether you're going to be lazy, whether you want it bad enough, and a lot of people like, "It's a lot of work. I don't want to do it." When the going gets tough, people are like, "I want to go remote. I have to do work? Maybe I won't. Maybe we'll just stay in nine to five." Just adding to your story, Matt, and I wish I had ... I have the screenshot, I wish I had it to share with everybody. But I had a client before and her approach was emailing employer saying, "Hey, are you hiring? I could just do stuff. Whatever you want me to do. I know you're remote."

Kate Smith (00:35:57):

Then we switched her strategy and similar to you, creating that value added piece. She was applying to this travel company and she created ... She did a research, saw that they wanted to run excursions or whatnot in Florida. So she created an itinerary for a Florida trip, knowing that that's something they have upcoming, she mimicked the itinerary style. And the email response was just like, "Wow, tell me more about yourself." She didn't even have to ask, they were like, "Tell me more about yourself. This is incredible." She could easily demonstrate that she did the research, that she cared, that she put in the effort. And so doing things like that, just what you shared it's similar to your situation, people will create jobs for you even though there isn't one available when you do things like that.

Matt Hollingsworth (00:36:44):

Yeah, totally. Totally. I think a piece of that is doing some research as to which company that you want to work for. Finding either the person or company. Sometimes it's just an individual and you can find a way working for them specifically. But doing your research, figuring out companies that align with what you believe in, what you want to see happen, and whether that's ... In any sector, there's always some company that's going to align with what you want to do and shares the same values. That's an interesting piece.

Matt Hollingsworth (00:37:15):

We have some resources on our site that just show top remote companies specifically. That might be a good place to look, these are folks that we know to be very successful in hiring remote workers, have a lot of experience in it. But there's companies all over the place that are really great companies led by really interesting people. So that's something to think about as well.

Kate Smith (00:37:35):

That's actually how I started my search. I didn't know anything about remote work when I started and I saw this big list of remote companies and I went through one by one, "Okay. What kind of job openings do they have and do I fit with any of them?" Another side note as well as you're applying, get feedback from employers, you know, "How could I be a stronger candidate?" I remember going through my journey myself, I was so close to getting this one opportunity as a project manager but I didn't get it. And so I asked the hiring manager, the person that interviewed me, I was like, "Hey, how can I improve for next time? How can I build up my skills to be stronger?"

Kate Smith (00:38:10):

And she was like, "Here's this e-book that takes you through a whole style of project management. If you read this and become more comfortable in this approach, you would be a stronger candidate." So can you imagine the power of me reading that book, they have an opportunity come up in the future and I'm like, "Hey, I took your advice. I read that book, I see you have an opening." They'll be like, "Holy shit, you actually took my advice." So ask for feedback. You can't read their minds of why they didn't hire you so if you can get feedback, that helps as well.

Matt Hollingsworth (00:38:40):

Yeah, yeah. Totally. So shifting gears a little bit, because I think we're going to come up on the end of the regular session here. I wanted to touch on this because I think it's important. Again, there's a lot of remote workers out there now looking for work, the space has become more competitive, things are really hard and totally don't want to diminish that component of what we're talking about here. I think that it's easy for people that have jobs to not really understand or know the experience that are without work right now. So I wanted to just say that.

Matt Hollingsworth (00:39:17):

I think, for some people, finding a remote job and applying for jobs just in general, whether it's remote or not remote is really hard, and often it's even anxiety provoking. So do you have any advice for people that just feel so overwhelmed that they don't even know where to start and then they just don't start at all? Is that something that you're finding or is that ... Do you have any thoughts on that?

Kate Smith (00:39:46):

There's probably [inaudible 00:39:47] they have fear. I actually get [inaudible 00:39:53] I don't know if I was ... Can you hear me okay?

Matt Hollingsworth (00:39:58):

Yeah, you're coming up just a little bit, but I can still hear you. Yeah. Sorry, folks. Okay, so it looks like your video is frozen there. I think well, Kate is just going to come back in here shortly. While we wait for Kate, and let me know if you guys can still hear me on the right hand chat. If anybody can let me know. Okay, great. So I'm actually going to start by answering a few questions here, Kate. Can you hear me now?

Kate Smith (00:40:38):

I'm back. Sorry.

Matt Hollingsworth (00:40:42):

Yeah, sorry. So I think you cut out just by when you were started talking about the anxiety piece of the puzzle here and try to get around that.

Kate Smith (00:40:49):

Yeah, I think it really comes down to just getting started and just doing it, and I think you have to have expectations that for every, say, 10 jobs you're going to apply to, you're not going to hear back from nine. Like that's just part of the process. Be okay with it. It doesn't mean you suck at all. It just means the right opportunity is out there for you. It's just you just have to find it and you just have to get there. But just be relentless and don't give up. Like I remember through my journey, I faced it, I faced so much resistance. And all the signs were going against me, so much so that once I landed in Prague, my laptop actually died. And I obviously did not have the money at the time. And I remember just like crying in the grocery store being like, "That's it. I have to go back to Canada. This isn't working."

Kate Smith (00:41:36):

And then I made a decision there. And I was like, "No, I'm not, I don't care. I'm going to do anything to make this happen." I ended up putting it on a credit card, the computer, because I needed that to work remotely. In that moment, I didn't realize it at the time, was the most defining moment because had I gone back to Canada, this may not be my life right now. Having traveled the world, worked remotely for five years, that was the critical moment. And a lot of you are probably in that moment. You have a choice. And that's the biggest thing to recognize is that there is the choice. The choice is there. And it's as simple as just take it one step at a time. Okay, find a job that you are interested in, send out that cover letter, send out that resume.

Kate Smith (00:42:20):

As long as you're learning as you go, and trying to learn as you go, okay, what's working? What doesn't seem to be working? What industries or spaces am I hearing back from? What industries or spaces am I not hearing back from? And recognize that it's okay if a company doesn't get back to you, that's just part of the process and it should be expected. As long as you never give up, it's a matter of when it's going to happen, not if. This isn't a situation of if you will get a remote job. It's a situation of when, and how that happens is determined by your dedication and your willingness to make that happen.

Matt Hollingsworth (00:42:54):

Yeah. Yeah, I know, I totally agree. I think the key piece that I want to reiterate to, if people out there are interested just the idea that doing the same thing over and over again for the same kinds of positions and not hearing anything is a sign that something needs to change, right? So, and again, like it can be discouraging, especially when it comes to months and months into the process and you're just like doing the same thing. You're kind of cut and paste, cut and paste, that kind of thing. That means that you need to change things up and try something new and be creative.

Matt Hollingsworth (00:43:28):

Get creative with it, try the things we're talking about. Try to get in touch with somebody that's part of the company, ask them questions, learn about the company. This is a kind of unique example of this. I was listening to a podcast with Jason Fried of Basecamp, and he was saying that when they hired their head of marketing position, there's obviously so many people that are wanting to get involved with this company and apply for this position. One person who actually didn't end up getting the job, but it ended up giving getting her like 30 or 40 pages above everybody else, just relative to where she was, was she put out ...

Matt Hollingsworth (00:44:04):

She bought a LinkedIn ad and targeted Jason and while the poll ... Everybody that works at Basecamp, but Jason ended up seeing it and said, it said, it had her face and it said, "Basecamp, hire me." And it linked out to an online profile, which I just thought was so cool. And he appreciated obviously, didn't end up giving her the job, but like that, you know, I think that would have been the difference had she had the qualifications. It's just such a cool, unique thing to do, I think.

Kate Smith (00:44:31):

And just to add to that, as well, in terms of what to do, what I do find that people will do sometimes is they take this false action towards landing a remote job. And what that means is that they'll spend all this time researching, listening to podcasts, watching videos, reading blogs, and they feel like they're making progress because they're consuming all this content, but they're not actually doing anything to move the needle forward. They're not putting out those resumes. They're not putting out those cover letters. So I would caution everybody how you're using your time and take action that will move the needle forward. I think that's a big thing.

Kate Smith (00:45:06):

Another thing I noticed is that a lot of people will say, "Okay, I want to go remote. So I'm going to sign up for this course or that course to become a developer," for example, right? And at the end of the day, again, it's about do you know how to present your value? Do you know the skill and art of how to land a job? You can go take that course, but it's still going to come back to the fact of okay, great. Now I need to go and put myself out there. Just because the job is more in demand, I mean, it doesn't really matter. If you know that skill of how to stand out and have that edge, that will always serve you more. And of course, I'm always for leveling up, learning more, but I also find that a lot of people will use that as a sort of distraction tactic to the task at hand. So be mindful of that as well.

Matt Hollingsworth (00:45:54):

Yeah, yeah. That's putting yourself out there I think is the key to making something happen and just taking one step at a time, but sending out those resumes and doing it and getting yourself out there. So, okay, I was hoping that we could ... If you had anything else to add, we're just in this format here just let me know. We're going to send everybody to the links of where to find you. Obviously, after the fact, we have the Q&A before we wrap up, so was there anything else that we missed? Anything else that you think is important in this format?

Kate Smith (00:46:24):

I mean, there's a lot to say, and it's really a loaded question. That's how I got into what I'm doing now with the remote career coaching. I used to jump on calls with people for free for an hour and try to explain the whole process of how they can land a remote job, and there's a lot to it. And so that's why I do the remote career coaching now. I think that we've covered a lot of bases just to get people started. If there is anybody out here that wants that support and wants to like fast track that you guys can find me on Instagram, all that stuff, just at The Remote Nomad.

Kate Smith (00:46:59):

I have the ebook that I've just created, the designer's finishing it up. Matthew and Justin are going to send that out to you guys. And this ebook takes you through the step-by-step process of all the things that you would need to go from where you are now to landing a job and just ... It makes it a little more manageable having like a system in place instead of trying to like grasp at different ideas and whatnot. So if you guys are interested, afterwards you can download that ebook, too, and it will take you through the process just to kind of give you that starting point in your journey.

Matt Hollingsworth (00:47:30):

Okay, great. Yeah, we'll make sure we send that out. And I think it's important for people to have action items that they can take and really apply anything that's a practical way of getting started. Okay, so we're going to just the Q&A here. And what I'm going to do here is I'm just going to scroll through the questions and I'm going to answer the ones or we're going to answer the ones that are live or we think are most interesting. The first one here, we're going to answer this one live. So Jamie here asked, "For those of you who are transitioning industries functioned, or even both, would you consider taking a step back or down to get the remote position?" So I'll leave that one to you, Kate, to start.

Kate Smith (00:48:11):

Oh, okay. Is the question if people are making that transition into remote work and they don't quite have the skills? Or should people be willing to take a step down?

Matt Hollingsworth (00:48:25):

Yeah. So just transitioning industries or function. So essentially, you're going back into the drawing board again. And yeah, what would you do?

Kate Smith (00:48:33):

Yeah. I mean, that's up to you guys if you're willing to do that. Is that necessary? Not exactly. I think people may do that as an easy way to get a remote job, but you can certainly get a job and a career at the same level that you're at. Again, it comes down to understanding how to present yourself and have the edge when you're applying to opportunities. It may open the doors. I mean, personally for me, I would be willing to do that. When I went remote, I was like, "I will do anything. This is like my dream," I was so clear on that. So if it meant, okay, I have to take a step down to get started, for me personally, I would do that.

Kate Smith (00:49:13):

When I made the transition, however, I was making the same salary and everything that I made in my corporate job. I did make a career transition from project management to online marketing. So a lot of people, some people may assume, okay, I have to take a step down, or I have to demote myself or get paid less. That's not the case. You just have to find the right opportunities, connect with the right people, and present yourself in the right way so that you have those opportunities that are ... This is to continue your career, like these are professional real jobs. You can grow your career in the remote worlds. These aren't just like these random jobs.

Kate Smith (00:49:54):

Those scammy jobs are out there and you don't want those ones. You want the ones that can grow your career, where you can grow and flourish. So that would be a personal choice. It's not necessary. But again, if I'm looking back at my journey, that's something that I definitely would have done. I've done free work for people. Do I think free work is fair? Absolutely, not. I did a free internship for three months. I think it's like a [inaudible 00:50:21] and I think people should always get paid. I'm really big that my clients get paid their value and their worth. You want to feel valued. You want to feel that as an employee, it's important. So yeah, I think it's a personal choice.

Matt Hollingsworth (00:50:34):

Yeah. Yeah, I think it's a good point that you bring up, right. It doesn't just because you take a remote job, it's not necessarily that you are settling for something other than like a professional career. The professional careers out there, of course, we have lots of them on our site, and they're on other sites as well. But these folks are at the top of their field, and in a lot of case just happens to be that there are remote workers. So it's a good thing to keep in mind. Okay, so we're going to move forward. Paul here asks, I'm gonna answer this one live here. He asks, "I'm not used to working remotely. Any tips how to get mentally ready for work, to work from home, and make it feel like a work environment?"

Kate Smith (00:51:16):

Yeah, actually, this is a great point. I just want to mention to everybody that this whole work from home, a lot of people are now working from home for the first time in their lives. And I just want to reiterate and clarify that working remotely is not the same as working from home. Working from home, you're in your home, you're in your space. Even this, working from home, was an adjustment for me. It is like, "What is happening, I'm trapped in my house." Usually working remotely for me means, "Okay, if I want to go to Bali next week, I can go to Bali next week." "Oh, it's 12:00 PM, I want to switch things up. I'm going to go to this cafe and I'm going to work from there."

Kate Smith (00:51:53):

And you've got to choose these inspiring environments that make you more productive and effective as an employee. You'll become way more productive, by the way. So before I answer this question, I just want to reiterate the fact that working from home is different. This has been an adjustment for me having to work in my space. The biggest thing I would say in terms of working remotely, there's two main things. One, just always be on top of communication with your team. Communicate with them. "Hey, I'm starting the day today. Here's what I'm working on." "Hey, just wrapped up. Here's what I finished up." Keep in touch with your team. You'll be surprised how much communication happens with remote teams. So being good at communicating with your team is really important.

Kate Smith (00:52:38):

The other thing is you really need to set boundaries in terms of time management. When I first started working, it's like this. It's like this most beautiful and challenging thing at the same time because I remember my boss was like, "I don't care when you work. Just get it done." I was like, "Well, shit, should I like go to the beach for the day first? And then like work at night?" I remember being in Thailand, I was like, "Well, maybe I should spend the days at the beach." And I was like, "I don't know." And then I was just always kind of working because I didn't really know or have a schedule. So I would strongly encourage you stick to a schedule and routine.

Kate Smith (00:53:12):

Eventually, I found that, okay, I'm going to start work between 9:00 and 10:00. I'm going to take a break during the day. And then I'm going to make sure I'm offline by 6:00 PM. So set those boundaries, otherwise, it will feel like you're always working and never working at the same time and feeling like you should work. And it can change. Do what works for you. If you're a night person, work at night. Who cares, right? Don't feel like, "Oh, I've got to work in the morning because society says work in the morning." Just do what works best for you and what makes you the best employee.

Matt Hollingsworth (00:53:45):

Yeah, yeah, totally. And your company that you work for will likely have especially if they're new to remote work they'll luckily have something in place in terms of the expectation there. And if they don't, then they put a lot of trust in you to make sure that you're doing things effectively and you're making sure that you're doing your work. I would add on to that, too, like so what Kate, what you've been doing is definitely one of the options for remote workers and that sort of remote, the nomad lifestyle and being able to shift around a lot and go to different places and stuff.

Matt Hollingsworth (00:54:21):

But also, just keep in mind, too, that there are ... It's okay to not be okay with that. Like it's okay and like just like you said do what's best for you. If you need some structure, if you need to ... Even if you need to work nine to five and you're in an office-like setting, if you set yourself up at home in office-like setting and you need that, any of that kind of structure then that's totally okay, too. It's not like you need to go out and feel like you should go travel the world if you are a remote worker, right? It doesn't work for everybody and it's okay to not have that.

Matt Hollingsworth (00:54:51):

And so you know, I think just to your point, Kate, for myself, I, as well, Need a lot of structure. I need to have a ... I'm a very routine-oriented person and I have to have a specific part of my day that is structured for different things. And so that's really important. I think being an effective remote worker is really about knowing yourself very well. And knowing how you work and knowing what situations you work best, and so that's hard. It's definitely hard to know, to figure that out right off the bat. But the nice thing is, is that there's times where you can trial and error that if you're not feeling.

Matt Hollingsworth (00:55:31):

If you're feeling [inaudible 00:55:32] that at home, obviously, situation is different. So pandemic remote work is not remote work, in general. So just keep that in mind, too. These are different circumstances and everybody's feeling pretty isolated. But when things do turn back to normal, if you are working remotely, I would make sure to just emphasize going out and doing it even if you're introverted going to Coronavirus-working space, go to a coffee shop, be in front of people, around people, and that'll help.

Kate Smith (00:55:55):

And just adding to that, be patient with yourself as you figure it out. I remember I thought, "Okay, maybe I'll go to the gym in the morning, and then I'll start work for the day." And I remember that doing that made me feel really overwhelmed like I was behind on the work day when I got started. So instead of freaking out about it all day, I just thought, "Okay, cool. This isn't working for me. Tomorrow, I'm going to try something different." So just try the different things and be patient with yourself as you're learning.

Matt Hollingsworth (00:56:19):

Yeah, totally. Okay, so that was maybe the longer ... I think we covered a few other questions in there as well. So hopefully, Paul, that answered your question and maybe answered a few other ones here as well. So we have time for a couple more questions here as well. So there's a few actually questions and I'm going to try to kill two birds with one stone here with just the topic of ATS in general. So there's a few questions in here that are related to standing out when it comes to applying through an ATS. Which is a really tough thing to do, and I think it's also important to know if you are applying through an ATS in general, right, so right off the bat, I'm going to kind of answer my own question here as well.

Matt Hollingsworth (00:56:59):

So, general tips to set out when applying through an ATS, I would say know that you're applying through ATS in the first place, which it can be hard to know. But oftentimes the major ATS companies will have what's called a sub domain in the URL. And that will be either an example that was like Greenhouse [inaudible 00:57:16], for example, the company that you're hiring for leavers, another one, things like that. They're usually pretty structured, and they're usually pretty foreign based and that sort of thing. So I would say know if you are applying through ATS is the first step. And Kate, I'll leave you to the other section of this. I took the easy part. Sorry about that. So how would you set yourself apart from when a company is specifically applying for an ATS? Is it kosher to go ahead and go to somebody else that works in the company like LinkedIn, reach out there? Like what would be the suggestion?

Kate Smith (00:57:49):

Yeah. I would say understand that yes, with an ATS, you're writing for a robot, in a sense, and you want the keywords. But you're also writing for a human. It's going to go through the machine first, then it goes to a human. So you want to write it in a compelling way. So keep that in mind. In terms of yeah, again, like if you've already had these informational interviews with people at that company just to say like, "Hey, the company seems so cool. I just want to learn more about it. Can you tell me more?" Like those are all simple ways. It depends on the company and their process. Some companies are like, "Do not follow up with us. This is our process, follow it."

Kate Smith (00:58:30):

Some companies are more open, right, like creating an ad on LinkedIn. That's a very creative approach. Right? So I think yeah, it's really going to depend on the company. And another thing as well is that with these referrals, like to get a referral into a company is huge. I'm just going to touch on this really quickly. There's so much power in growing your network in this remote workspace. So for example, when I was trying to go remote years back, I was connecting with people in the nine to five environment. And they had these traditional jobs. Not surprisingly, all I could find were traditional jobs.

Kate Smith (00:59:10):

When I booked my one way flight to Prague, I was working at a coworking space. Coworking spaces are full of remote workers. Those people when their boss needs to hire someone, they're going to say, "Hey, we need someone to do this. Do you know of anyone?" And that remote worker will be like, "Oh, yeah, I know this person or that person." So and that being said, sometimes, and often referrals don't have to be from a specific person at that company. So it could be like somebody who knows somebody. For example, when I landed my job, I was at a coworking space, full of remote workers. My friends invited me for lunch and they're like, "Oh, yeah, these locals going to come with us." It's like cool.

Kate Smith (00:59:47):

We're having a conversation. I mentioned that I do online marketing. He's like, "Oh, my friend is looking for somebody to do online marketing." And of course, it was a remote opportunity because everyone in a coworking space works remotely. And so through that referral through somebody that he didn't even know me, we just connected over lunch one time, I got my remote opportunities. So I think it's huge to tap into that network and that space as well.

Matt Hollingsworth (01:00:13):

Yeah, yeah, totally. Yeah, the ATS one is a hard one. I think you do have to know the company pretty well. I think there are cases where people will, let's say for example, if they have an ATS and you want to apply for that job, go into the hiring manager ... And this is another question somebody asked as well, is it okay to go try to find the email somebody that worked for the company and then just go directly to them? Again, it's so company specific. I think most people go through ... They'll send you the ATS either way, so it depends on how you want to present yourself, and it depends on the company you're applying for.

Matt Hollingsworth (01:00:50):

So I don't have a good answer for that. I think it's a really tricky one. Because people they're getting so many applicants that oftentimes what they'll do is they'll just say, "Please go to our ATS." And again, it's a really hard question. And I don't have a good answer for that. I would say that get creative folks on referral network, focus on trying to make something [inaudible 01:01:13] a connection to the company outside of just the regular ATS. Then making sure that your cover letter and resume are [inaudible 01:01:19] back if that is through ATS. So hopefully, that helps people.

Kate Smith (01:01:24):

Yeah, absolutely.

Matt Hollingsworth (01:01:26):

Okay. Well, we're at 3:00 o'clock. There's so many good questions here, folks. And I'm sorry, we won't be able to get to all of them. One of them here, I was just going to find ... There's a few people that are asking about ... And we'll use this as our last question here to wrap up. There's a lot of you asking about remote experience and how important, or oftentimes will say ... As we've seen as well and it were always the same thing, people ask for a specific amount of remote work experience before applying for a job. What do you suggest for people that want the job maybe qualified for the job outside of the role experience? Do they apply anyways? What do they do?

Kate Smith (01:02:10):

Great question. There's a few ways to address this. So the first one is to consider okay, in any capacity have I partially worked remote? Occasionally worked remote? So maybe if you've worked remote once a week or once a month with your company over the last year, that could be occasional remote. Have you had a volunteer experience? Something like that where you were communicating with people remotely? So keep in mind that it doesn't necessarily ...

Kate Smith (01:02:38):

There could be instances where you have partially or occasionally worked remote. You know, maybe if you're in let's see, Denver, Colorado has got a lot of snow. So maybe you worked from home during the snowstorms and you have that occasional experience. So you can specify whether it's partial, occasional, full time remote experience. It doesn't have to be in a professional setting. It could be in volunteer experience. So maybe go volunteer somewhere where you can build up that skill.

Kate Smith (01:03:07):

Another thing to keep in mind is that the biggest thing is they want to see that you have the skill and capacity to work remotely, even if you don't have specific experience. So that means are you a good communicator? Can you manage your time effectively? Are you self-motivated? Can you just get shit done? So looking at those soft skills, and demonstrating how you've used those skills in the past can go really far if you've never had remote specific experience.

Matt Hollingsworth (01:03:36):

Yeah, yeah, I totally agree. And again, having been on the other side of it, where we had asked for more experience before and this is just a personal preference for us. And one of the things that we were looking for at the time when we were hiring for these folks, is just that self-motivation, right? So a lot of it is we're not going to be looking over your shoulder. We need to trust you to be able to do your work. I'm always of the mind that I think everybody should apply for the job. If it's close, obviously, you don't have to meet all the criteria in the job description. But I think it's important that people go and put themselves out there and go apply for a job anyway.

Matt Hollingsworth (01:04:11):

I think one of the things, like you said, their remote work experience just tells us that you can be at home and you can be productive, and you can do your work, and we can trust you to do that. So if you have cases where maybe you're an entrepreneur, and you started something from scratch, and you're able to get something done, you're scrappy, and you made something happen on your own. Some note that and get creative with the way that you approach the application process. And so it just is about activity. It's about showing that you could actually make something happen for yourself and you don't need a kick in the ass to be able to do something, right.

Kate Smith (01:04:48):

I think that's like a big thing to note as well is to know somebody who worked in an office and they'd have these random days where they'd work from home. And I remember I was with them one day and they get up and they'd like, turn the TV on and they're like, they're not doing anything. I'm like, "What are you doing?" And it irritates me because I'm an advocate for remote work. And you have people that ruin it because they work from home one day, and they actually don't do any work. So I think it's, I don't know, just going off of what you were saying, Matt. But I forgot where I was going with that. Oh, man.

Kate Smith (01:05:21):

Well, first of all, don't be that person. And just demonstrate that you're not that person. And I think that's why so many nine to five traditional companies right now are struggling because they don't trust their employees. Remote work companies, they trust their employees. They trust the people that they've bought on, that they've hired me and they're like, "Look, I trust that you're going to get this done." Where people in that traditional environments they just simply don't trust their employees. So what you're saying it's a matter of okay, can we trust you to get stuff done?

Matt Hollingsworth (01:05:53):

Yeah. Yeah, for sure. And a company's now, I think, hopefully you're moving in the direction of not just you don't have to just be in your seat to be considered someone that needs to whether it's productive, because more often that's not even the case in the first place. So I think most companies are looking for people that can produce and have the output is the thing that they're concerned about and measuring for. So output as opposed to just being there I think, is really the important thing. All right. Well, should we leave it there, Kate? Again, there's so many other questions here.

Kate Smith (01:06:27):

I know.

Matt Hollingsworth (01:06:27):

They're all so good. So there's even a couple of people that are asking are these questions going to be answered after the fact, and how they're going to get it up to folks? We don't know the answer to that. I'm hoping that this saves and I can take all these questions and answer them our own way. And hopefully what we can do is repackage this and put it out there as a blog post or something like that. Your names obviously won't be associated with it so that's totally fine. You'll be all anonymous. We'll try to get in touch with them afterwards and figure it out. Just to wrap up here, Kate, how can people find you? There's been a couple of people that have been asking. People can find you on social, I'm guessing. Where can they find you?

Kate Smith (01:07:06):

Yeah, yeah. I'm most active on Instagram stories. So @theremotenomad, and again, I would strongly encourage you guys, if you're interested in going remote, get that free ebook that Matthew and Jesse will be sending out. Yeah, if there's anything else, just feel free to reach me. I would say probably Instagram is the best spot, just shoot me a DM. And I just want to thank everybody. There's so many questions here and I was telling Matt, he was like, "How long should we make this?" I was like, "I could talk about this forever." We could go really long with this. But you know, we only want to keep it so long. So I just appreciate all you guys showing up today and all these incredible questions. You know, Matthew, hopefully, we can figure something out to get at least as many of these questions answered because they're so great. And I'm sorry that we can't get to them all today.

Matt Hollingsworth (01:07:58):

Yeah. We really appreciated everybody showing up and engaging. And hopefully, this was helpful. This is a new thing for us. And let us know if this was helpful. And we're always wanting to hear your feedback. And if this was helpful, and maybe you have another suggestion, please do let us know. You can either reach out to us, me directly. We'll also provide all the contact information after the fact as well. Follow us on Twitter, @weworkremotely. Go to We Work Remotely if you're looking for a job, all that kind of fun stuff. We will be in touch. We'll put that ebook in email we send afterwards as well as this recording so you can, if you want to listen to my annoying voice more, you can do that. But yeah, anyways, I really appreciate everybody and Kate, thank you so much for being here and we'll talk soon.

Kate Smith (01:08:44):

Awesome. Yeah. And thank you so much, Matthew and Justine for inviting me today. This has been really great and really fun so thank you.

Matt Hollingsworth (01:08:50):

I think it's due for a part two, Kate, so maybe we'll line that up.

Kate Smith (01:08:53):

Yeah. For sure.

Matt Hollingsworth (01:08:55):

All right. Thanks, everybody.

Kate Smith (01:08:56):

Thank you.

Matt Hollingsworth (01:08:56):

Thanks so much again for listening to the show. Be sure to check out for the latest from our jobs. If you're looking to hire your remote worker, We Work Remotely is the fastest and easiest way to do so. As always, if you have someone you should talk to, any advice you have, or if you'd like to advertise on the podcast, please reach out to us at That's Thanks so much again for listening and we'll talk to you next time.


Key points in this episode

Welcome to Season 2 of the Remote Show! We’re kicking off 2020 at The Remote Show with Scott Mathson, who runs Web Strategy, Growth, SEO at Netlify and also is the bootstrapped founder of Plink. We were super excited to chat with Scott, as he is an ever present name in the remote work and bootstrapped founder communities.

We get into all kind of interesting topics from his background in woodworking, his experiences at Auth0 to taking on his new role at Netlify and bootstrapping his new startup Plink (Scott graciously created a free subscription Plink custom link for listeners of The Remote Show (and desktop Show Page, Episodes Page). Scott is another great example of someone who is insightful, honest and open about his work experience about burnout, career progression and the pros and cons of working remotely. 

Scott is a mentor at Lambda School and one of his initial mentors was Pete Sveen. For those of you interested in woodworking and DIY projects, you should check out Pete : -)

Burn out resources mentioned: journaling, therapy, scheduling in self care time, mindfulness & meditation - Headspace, MacOS Aware App , Pomodoro techniques, Coworking, etc.

Scott’s book he’d force everyone to read: Into the Wild by Jon Krakauer. 

Find out more about Scott at:,, and Mathson Design Co. You should all check out another project of Scott's: Makerviews, a place to share the stories of and advice from a variety of makers, designers, and artists. 

Please enjoy!

Key points in this episode

In this wide ranging conversation, Laïla and I dig into a number of relevant topics when it comes to remote work. What has been particularly interesting for me, as many of our listeners probably know, is the idea of company culture on a remote team and how best to optimize it. One of the key takeaways from our chat was the importance or one on one check-ins with team members, and what happens when someone is feeling off or not 100% in their work. Laila gave a unique perspective on this, as well as asynchronous communication, hiring, design thinking/collaboration on a distributed team. 

Mural is a leading digital whiteboard product that empower modern teams to visually explore complex challenges and collaborate on researching, brainstorming and designing ideas. Go to to find out more and start collaborating more effectively.

Follow Laïla on Linkedin at and Twitter at @lailavona, and her personal website at:

Key points in this episode

Career Coaching is something many people hear about, but not many of us get the chance to enjoy and benefit from. Prosper is looking to change that. They are bringing personalized 1-1 coaching to the masses by creating a online, scalable platform for coaching professionals into the next steps of their career.

It was a pleasure to learn from Beckie’s backstory working in corporate environments and entrepreneurial endeavors, before she began Prosper. We discuss the shifting landscape of business, how Prosper came to be in its current form, what career coaching can do for professionals and organizations, and how to find and nurture mentorship type relationships.

Beckie is a true professional in every sense, and I hope you get as much out of this conversation as I did!

If you’re interested in trying Prosper and benefiting from their coaching services, or providing it for your organization, please go to to find out more.

Also, be sure to follow Beckie on Linkedin and Instagram at B. Thain Blonk

Beckie’s book she’d force everyone to read: Think, Learn, Succeed by Dr. Caroline Leaf


Key points in this episode

Hubspot embraced remote work early, and continues to innovate on best practices and lead the charge in building a large business around a remote first mindset. It was great to dive into what a “remote first mindset” looks like for them, practically speaking. Meaghan is truly at the forefront of what a successful remote first company looks like, and I’m sure we’ll see other large remote companies follow in Hubspot’s footsteps in hiring for a similar positions to Meaghan's. This conversation was a wakeup call for us in the sense that leading technology companies are embedding remote work in their DNA. Anyone who is interested in promoting a healthy remote first culture, or is searching for tips and tricks on what to do first in building a successful remote team for companies with limited resources, should pay attention to what Meaghan has to say. We certainly are taking her lessons to heart!


Hubspot is hiring remote workers all the time. If you’re interested, you should check out

Make sure to follow Meaghan on Linkedin and make sure to check out and find out how their moving remote work forward!

Meaghan's book she'd force everyone to read: The first Harry Potter book: Harry Potter and the Philosopher's Stone

Thanks for listening!

Key points in this episode

This week we’re excited to share our conversation with Patrick Mckenzie. Patrick is many things, but at the moment is primarily a senior individual contributor working on Content and Community at Stripe. Prior to Stripe, Patrick was a successful entrepreneur who started four different SAAS businesses. His blog is a catalogue of knowledge (with 565 essays written) for anyone interested in technology, entrepreneurship, engineering or business. Find it here.

To many (including yours truly), Patrick is an internet legend; he has started four software companies, is a prominent writer, software engineer, marketer and researcher who’s interest spans many fields. I encourage you all to follow Patrick on Twitter at @patio11 if you’re not already - he is one of the few people we can honestly say can make you a more successful entrepreneur just by reading their Twitter feed. Broadly, Patrick and the Stripe team are working on increasing the GDP of the internet. The crazy thing is, they’re succeeding in a big way.


Patrick’s current role at Stripe is, as he says, “squishy” which means he works on many different things, including helping write the Stripe Atlas guides, contributing to marketing efforts, writing code, hiring and much more. Stripe recently announced that they were hiring remotely on a wider scale, so we were able to dig into that decision process and understand more of the internal workings of the remote culture at Stripe.


There’s a lot to unpack here, I could talk to Patrick for an additional hour if it time would allow. Please enjoy our conversation!

Stripe is hiring aggressively for remote roles. If you’re interested in working for Stripe (which you should be), please visit

If you’re not already using Stripe for your online business, then I don’t know what you’re doing, but you should switch to them now by going to and signing up for an account.


Some people don’t know the extent of Stripe’s value to online businesses. If you’re an internet entrepreneur, you can benefit from the Stripe Atlas Guides, the Stripe Sigma business analytics and many other products they offer. Find them all at

Follow Patrick on twitter: @patio11, or email him directly at

Thanks for listening!

Key points in this episode

Hopefully this was valuable to our listeners! If it was, please do continue to ask questions via our inbox and we’ll collect questions for our next AMA. If not, we’ll be back with a new guest for our next episode!

Thanks for listening!

Key points in this episode

Matteo has a long history of working remotely, beginning his distributed work journey at Shopify before taking the lessons learned there and applying them to Eli-Z group. Matteo began as a marketer in the company, and now overseas all departments in his role as Chief Operations Officer.

One of the areas that I found interesting was Matteo’s approach to work life balance and how he keeps a pulse on how his employees are feeling in work and in life. With his background in Psychology, Matteo is particularly in tune with the nuances of a distributed workforce and its effect on employees well-being. This conversation will be particularly valuable for managers of a distributed work force! Please enjoy!

Be sure to go to: for more information about their business and how they help e-commerce businesses.

Find them on facebook at:

Matteo’s book he’d force everyone to read: The Alchemist by Paul Coelho

If you’re looking for help with remote work compliance, check out for payments to contractor, for EU tax compliance.

Key points in this episode

What struck me most when talking with Hiten was the clarity of his thinking and his honesty/transparency. The beginning of the conversation went in a unique direction, and I’m glad it did as it allowed us to discuss some of the more nuanced and complex dynamics that arise when building businesses from nothing. Hiten has been in this industry and creating products for many years; he spoke to the evolution of his thinking in many areas, including giving advice, pressure and removing mental/emotional road blocks instead of breaking them.

We of course talked about remote work in depth. Having built many different distributed teams, both self-funded and vc backed, Hiten has some interesting and valuable insights when it comes to remote teams. This was one of our most interesting and in depth conversation with a leader in the remote work space. I hope you enjoy it as much as we did!

Hiten’s current company, FYI, is working to solve one of the major issues of remote work by making it easier to access and organize documents. You can check what he and his co-founder Marie Prokopets have built at

Also, be sure to check out their Remote Work Report, one of the most comprehensive handbooks to all things remote work, and one that we were lucky enough to contribute to!

And of course, follow Hiten on Twitter: @hnshah

The book that Hiten would force everyone to read: The Courage to be Disliked by Alfred Adler

Key points in this episode

A true generalist, Matt has his hand in everything from product, marketing, podcasting, design and partnerships at 1Password. He was kind enough to share his thoughts on everything from building remote teams, the public perception of online security, the motivations of data hackers, what you can do now to increase your online security and much more. Security online is a massively important component for everyone with an online presence, but even more so for people and companies working remotely. Matt was an absolute pleasure to speak with, and we’re glad to share the 1Password product and team insights with our community.

To get yourself more secure in a user friendly way – check out now.

Follow Matt on Twitter at @mattdavey

Matt’s book everyone should read: “This is Going to Hurt” by Adam Kay

Find 1Password on and to take part and claim their bounty on security vulnerabilities.

Key points in this episode

Z1 is a digital product studio with expertise in transforming business ideas into incredible digital products. Z1 helps founders and growing startups design and ship first iterations of a product to market, or polish the user experience of a V1 product ready for the next stage of growth.

Working from beautiful Vancouver BC, Canada, Michelle leads the business development side of things for Z1 while the rest of the team works from Spain. We were able to dive into what creating solid relationships for global clients looks like, the importance of company culture in a semi distributed team, and much more. I hope you enjoy this conversation as much as I did!

Make sure to connect with Michelle on Linkedin at:

Also, check out Z1 Digital to see the great work they have done, and follow them on social!

Michelle’s book she’d force everyone to read: Grit, by Angela Duckworth.

Thanks for listening!

Key points in this episode

This week we’re excited to share our conversation with Jason Fried. As many of you know already, Jason is the Co-Founder of Basecamp – one of the world’s leading software applications for communication and team productivity. He is also the co-author of "Rework", "Getting Real", "Remote" and most recently "It Doesn’t Have to Be Crazy at Work".

Jason is a brilliant communicator and was a pleasure to talk to. We dive into things like his decision making process, the state of tech as an industry, downsides of remote work and much, much more. One of the things I believe attracts people to Jason’s work is that he is honest, straightforward and clearly very knowledgeable. As a result, he’s got a refreshingly original take on most things. I hope you enjoy this conversation as much as I did.

Please make sure you follow Jason on Twitter at @jasonfried and check out his writing on the Basecamp Blog: Signal vs Noise. Also, check out their latest book – Shapeup, which is (in typical Basecamp fashion), available online for free. Find it here.

If you want to make work feel like less work, check out Basecamp and try the product for free today..

What Jason’s reading regularly: by Jason Kottke by Andrew Sullivan by John Gruber

Berkshire Hathaway’s letter’s to Shareholders, by Warren Buffett. Compiled version, found here. Or for free on the Berkshire Hathaway Website

Key points in this episode

This week we were able to speak with Kristi DePaul, the Founder and CEO of Founders Marketing -- a marketing agency devoted specifically to the future of work and future of learning niches. Kristi is also a popular writer, speaker, startup mentor and has extensive experience in both executive roles in the remote work space and now through her role as CEO of Founders Marketing.

Kristi was great to talk to and learn from. Like many of us in the technology space, she’s got an interesting background and took a relatively unconventional route in becoming a successful entrepreneur. We were able to dive into what makes her team unique in the crowded marketing agency landscape, her thoughts on team building and much more. Of the many things we discussed, I think my favourite was how her background and training has affected her work and her entrepreneurial journey.

Thanks for listening!

If you’re in need of marketing help, or interested in what Kristi and her team are up to, please check out for more information.

Book Kristi recommends: “Wild” by Cheryl Strayed

Key points in this episode

Starting in academia, Tammy shifted to Ed tech and began her own business consulting. She then saw the gap in education and training related to remote work, and she has been building Workplaceless to fill that gap.

Tammy is a true pro, and had some quality insights about remote work culture, communication and major pain points related to managing and building remote teams. What I really enjoyed about our conversation, however, was how genuine Tammy is. Her best advice: “Not taking yourself too seriously” is one of my favorites, and I think isn’t heeded as much in business and entrepreneurship.

Check out and check out their wonderful remote work training options!

Follow Tammy on twitter: @TammyBjelland

Tammy’s book she would make everyone read: “Behold the Dreamers” by Imbolo Mbue

Key points in this episode

David’s first foray into remote work was working for a Joseph Liemandt company called Versata, where he was a global operations manager. David then led to a number of other managerial roles in the software space before starting his own consulting firm called The Mega Agency and software company called Hubackup. He also is a Product and Marketing Lead for OntheGoSystems, is pursuing a PHD in Global Business and is working on his own podcast.

My favourite part of the conversation was learning about David’s experience and his view that success can be achieved by jumping in, taking responsibilities for outcomes, and finding ways to be valuable. David has more energy than most, but the principles he talks about can be applied to anyone.

David’s book he recommends everyone read: Think and Grow Rich by Napoleon Hill.

Check out David at: and on Twitter at @imdavidpeterson

Also check out and

Key points in this episode

This week were were fortunate enough to chat with Sarah Park! Sarah is the President of MeetEdgar, a popular social media scheduling tool. Sarah was an absolute pleasure to chat with; we were able to dive into her career, how the company has evolved and what "culture" means at MeetEdgar!

I found Sarah's career particularly interesting to learn about; she is a great example of what can happen when you take advantage of opportunities, and you can't help but be inspired by her story. We spoke about what it means to grow culture within a company and what that looks like on a daily basis, how she continues to refine her decision making skills and the importance of being able to have productive difficult conversations. I learned a lot from Sarah, and I'm sure you will too.

MeetEdgar is a leader software tool for scheduling social media posts that enables you to focus your time and energy on more important aspects of your business. Check out for more information.

Also, follow Sarah on twitter at @itsmesarahp

Sarah's book everyone should read: Difficult Conversations: How to Discuss What Matters Most

Other things mentioned on the show: The Knowledge Project, a podcast by Shane Parrish at Farnam Street:

I hope you enjoy our conversation as much as I did!

Key points in this episode

In this episode we were able to talk with Liam Martin, the Co-Founder of Time Doctor, and Running Remote. Liam is what we’d consider a "remote work expert". He has spent many years building successful remote companies and talking to remote founders. We were able to really dive into the data and discuss the current state of remote work, what the future might hold, and much more.

Liam is the Co-Founder of Time Doctor, one of the leading time tracking software tools for remote teams. One of my favourite parts of talking to Liam was diving into the data he has aggregated with his work at Time Doctor, and the insights that we can pull from them regarding the remote work phenomenon. Things like: How many hours of productive work a day do we average? How many people are truly living the "digital nomad lifestyle"? What are the implications of mass data collection on remote workers?

We also discuss in depth the conference he co-founded -- "Running Remote," which has become the world's #1 conference for remote work professionals. You can find more info on Running Remote at and Also, if you want to track your teams productivity (or your own), check out

Find Liam's book everyone should read: Day of the Triffids

Key points in this episode

Max is originally from Siberia and worked for many years as a software engineer, including 2 years at The Washington Post, before developing his product and his team. He worked nights and weekends before moving full time, and now helps manage his remote company of over 15 people from his home in Maryland.

This episode will be particularly interesting for you technical founders and software engineers looking to build a business around sophisticated technology, as Max has some really important insights. One in particular is their approach to accountability and ownership.

Used by some of the world's top companies, Sympli is a collaboration tool for UI designers and developers that streamlines design handoff and makes design implementation easy. Also, check out their new "Versions", a top version control tool for designers.

Max's book everyone should read: Why We Sleep, by Matthew Walker.

Key points in this episode

Rebecca's career has been shaped by jumping at opportunities that were presented to her. As a singer and extrovert, working remotely was somewhat of a shift for her. For those extroverts and are concerned that working remotely will make them feel isolated and alone, Rebecca has some tips for you! It is certainly possible to thrive working remotely as an extrovert, and Rebecca is a wonderful example of that.

Owl Labs’ mission is to solve a problem we’ve all experienced: meetings suck, and they are especially painful for the remote people on the other side of the call.

Check out for more information about the Meeting owl tool. It truly is the next generation f hardware tools for remote workers.

Be sure to check out Rebecca on Twitter at : @repcor

Also, check out Rebecca's book she'd force everyone to read: Radical Candor, by Kim Scott

Thanks for listening!

Key points in this episode

Workfrom is a platform connecting mobile workers and spaces to work. They're capturing the world’s workable spaces online and connecting a new generation of professionals with resources needed to thrive outside an office.

With they're new Homebase feature, you can get access to a flexible co working solution that works best for you! Check it out here.

Be sure to check out WorkFrom and join their community, and follow Darren on social at @darrenbuckner

Darren's book he would force everyone to read: Essentialism, by Greg Mckgeown

Key points in this episode

In our wide ranging conversation, we cover the building of the initial product and finding product market fit, building a remote team while travelling, the pro's and cons of being as transparent as they are, and much more!

Joel's journey is an inspiring one, and there are lots of lessons to be learned from the path that Buffer took to success. Joel is incredibly humble, intelligent and honest and it was a pleasure to hear him discuss his business.

Find joel on Twitter: @joelgascoigne

Check out his personal blog at

And if you haven't already, check out and make your social media scheduling a breeze!

Also check out his book recommendation: Joy at Work by Dennis Bakke.

Thanks for listening.

Key points in this episode

In this episode we were fortunate enough to talk to Wade Foster - Co-Founder and CEO of Wade and his team have built a massively popular product that has helped many businesses (including ours) automate their processes. We discuss the ongoing process of building a positive and productive company culture, how to be a better manager, his YC experience, early iterations of Zapier and much much more.

Like many successful entrepreneurs, Wade is a constant learner with a mindset that is focused on always improving. I particularly enjoyed our discussion around how his team manages feedback in an environment of kindness, and his humbleness when discussing his own journey of managing an ever expanding company.

Wade is also an impressive writer and blogger, and we discuss the importance of writing as a CEO.

Please check out and start a free trial if you haven't already tried the product. You won't be disappointed!

Follow Wade on Twitter: @wadefoster

Check out the Zapier blog:

Thanks for listening!

Key points in this episode

This week we're excited to share our conversation with Claire Lew, the CEO of Know Your Team. We learned an incredible amount from Claire about management, remote work, entrepreneurship and much more. Claire is one of the leading voices on how to improve your management skills and become happier at work. You're going to want to take some notes for this one! We certainly did.

Equally as interesting as the software itself, Claire's journey to where she is today is an inspiring one. From her early success to finding and developing a product that helps people, Claire has extensive experience yet remains incredibly humble. We think this is one of our better conversations, and we hope you do to.

Know Your Team is a management software tool that offers best practices, guidance and a community of peers to help you become a more effective manager. It is particularly popular in remote teams, and we highly recommend that you check it out if you'd like to improve as a manager!

Visit: and sign up for a free trial!

Please check out Claire's blog, found here:

And follow her on Twitter: @clairejlew

Key points in this episode

This week we had the opportunity to chat with Adda Birnir, Founder and CEO of Skillcrush. Skillcrush is a leading online education platform specifically orientated towards women in the tech space, with courses in programming, design and much more. A fully distributed team from the beginning, Adda had some great insights into the scaling a remote team, culture and what it takes to build a business! We covered a variety of other topics including leading a mission driven business, how to hire the right people, technical education and much much more.

Adda has an interesting back story from beginning her entrepreneurial adventure in the depths of the 2009 great recession, to building an original product (hint, it’s probably not what you think) and evolving the Skillcrush community to a team of 20+ people helping thousands of students find careers in the tech space. What struck me most about Adda is her passion for the day to day of building a business and her love of constant improvement. I hope you enjoy this half as much as I did!

Be sure to check out Skillcrush’s Ultimate Guide to Getting a Remote Job You Love handbook, found here:

Also, check out and follow Adda on twitter at @addabjork

Key points in this episode

On today’s podcast, I’m excited to share with you my conversation with Cesar Abeid! Cesar is a Happiness Team Lead at Automattic - the folks behind It was fascinating learning about his processes and getting a sneak peek at the internal structure of Automattic.

Something for everything in this one, as Cesar has a diverse background (podcast host, engineer, project management professional) and had insights and tips in many different areas. I found Automattic’s hiring process particularly interesting, as it is not one that I’ve heard of before (spoiler: they don’t actually talk to people they hire on a call until well into getting the job). Automattic is obviously doing something right, as they are one of the largest distributed teams around!

Interested in a job at Automattic? You should be. Check out their hiring page:

Also check out Cesar’s podcast Project Management for the Masses:

Key points in this episode

In this episode we talk to Ben Nelson, the Co-Founder of Lambda School. Among the wide variety of topics, we discuss the future of education, the story of Lambda School from small code bootcamp beginnings to leading educational resource, building a team, and much much more!

Lambda School is a revolutionary educational resource where students only pay a portion of their salary after they find a high paying job (over 50K annually), and the total amount charged is capped at 30K total. We talk about how the model has evolved and how this way or learning has enabled a huge group of people who wouldn't otherwise have the opportunity to study programming and online skills the resources to do exactly that. Along with this fascinating and effective approach to learning, Lambda School is innovating to ensure they are being as inclusive as possible by removing as many biases to and barriers to entry that typically exists for parts of the population in the technology space. Their Summer Hackers Program is a great example of that!

Ben also had one of my favourite answers to our closing questions: "What is the best advice you've ever been given?"

Please enjoy.

For more on Lambda School, please visit:

For their Summer Hackers Program, please visit:

Make sure to follow them on Twitter, Facebook and Linkedin also!

Key points in this episode

In this episode we talk to Gonçalo Silva, the CTO of Doist -- the company behind the popular communications app Twist and the productivity app Todoist. We get into hiring, focused work and building the future you want to work in! Gonçalo had some wonderful insights on remote work from an engineer’s perspective, as well as what he looks for in people he hires (it might be different from what you’ve heard before).

It was refreshing to hear an honest take on the struggles of working remotely, scaling a team and building a culture of innovation while not sharing an office; I think this was one of the best examples of the fact that even the most successful companies are still iterating on what it means to be a successful remote team. Doist is certainly one of the companies that is doing it right - their employee retention rate confirms that!

Please check out and their blog “Ambition and Balance”. Also, follow them on twitter at @doist and Gonçalo at @goncalossilva.

Key points in this episode

Show Notes:

This week it was our pleasure to talk to Field Marketing Extraordinaire, Design Evangelist and long time remote worker -- Max Lind! Max has extensive experience in design and creative work for some incredible teams. We discuss his career path from working in a design agency to becoming a senior business development specialist at Dribbble and his current role as Manager of Field Marketing at Abstract. Max had some great tips on working remotely, career advice for people wanting to get into the industry and much much more. Max is truly a gem, and we're happy we get to share his insights with you!


Check out, and follow them on twitter at @abstract for the latest on what they're up to! It's worth it, trust us. Also follow Max on twitter: @maxlind for some high quality gifs and updates on his work with Abstract

Key points in this episode

In this first ever recording of the Remote Show, It was my privilege to chat with Zack Onisko - CEO of Dribbble. In this wide ranging conversation we discuss his career in design and growth, the progression of Dribbble as an online community and tips for hiring and managing remote workers. Zack had some great insights about culture building in remote teams, hiring/retaining top talent and the importance of Emojis.

For those who don’t know - Dribbble is an online community for showcasing user-made artwork and serves as the go to resource for networking and feedback for web designers. They’re constantly looking for ways to showcase top talent from around the world and help great designers with employment opportunities, support and much more!

Please check out and follow them on social media! Also follow @zack415 to see what he’s up to.

Thanks for listening!


Matt H.: Hello, everyone. My name is Matt Hollingsworth, and it is my great pleasure to welcome you to the first episode of The Remote Show. On this show, we will talk to professionals in a variety of industries in positions around the world about their experiences working remotely. The pros, the cons, and everything in between. Along the way, we hope that we can provide some unique insights that will help you on your remote work journey. The Remote Show is brought to you by, the number one place to find and list remote jobs. Without 220,000 unique users per month, it is the best place to find your new qualified candidate.

[00:00:39] My first guest on my show today is Zack Onisko. Zach is the CEO of Dribbble, which is an online community for showcasing design work from some of the best designers in the world. It has grown to become an inspiration destination for hundreds of millions of people, now a go to resource for discovering and connecting with designers and creative talent around the world. Check out, that's if you haven't already checked that out.

[00:01:07] Previously, Zack was Vice President of Growth and interim VP of Product at Hired, Inc. Dribbble is now a 100% remote team with over 40 employees. With all that said, Zack, thanks for being on the show today. I'm not sure if you're aware, but this is the very first recording of The Remote Show.

[00:01:24]Zack Onisko: Well, cool. I hope to make it worth it.

[00:01:26]Matt H.: Yeah, I'm sure it will be, for sure, and we're super excited to talk to you today, so that's great. Thank you so much for being on.

[00:01:33]Zack Onisko: Thanks for having me.

[00:01:34]Matt H.: I'm sure most of our listeners have heard of Dribbble or know about Dribbble, but why don't we start with what you do at Dribbble and how things are going, and we'll go from there.

[00:01:43]Zack Onisko: Sure, yeah. So Dribbble is a global community for designers. We're gonna celebrate 10 years this summer, so we've been around for a while. It's a global brand. We have designers all over the world who come to Dribbble for inspiration, exposure, feedback, job opportunities, and yeah. I took over as CEO about two years ago.

[00:02:08]Matt H.: Nice, nice. So were you part of the community before you came on as CEO, or were you-

[00:02:15]Zack Onisko: Yeah.

[00:02:15]Matt H.: Yeah? Okay, cool.

[00:02:17]Zack Onisko: Yeah, I mean, so just a quick background on me, I started my career about 20 years ago as a web designer. I started a little freelance business for a couple of years, and then got a formal design degree and thought I was gonna go the agency route. Was really into Flash and motion design at the time and really loved that stuff. Then ended up taking a job at a startup and then my role kind of quickly moved out of design into product management and to more of a growth, executive roles at numerous startups over the course of the last two decades.

[00:02:54] Along the way, for one reason or another, my career trajectory has landed in companies that were either in the recruitment space or the design space, and so Dribbble's kind of in the middle of those two worlds. So anyway, kind of full circle.

[00:03:11]Matt H.: Yeah, that's great. I think it probably helps with getting the jobs in the executive and marketing and growth that you had, the background that you did. Correct me if I'm wrong there, but it seems likes these things tie all together, so.

[00:03:24]Zack Onisko: Yeah, I mean, when I met Andrew Wilkinson from Tiny, that was kind of how he found me, where he's like, "Hey, I found, I have this opportunity to run by you that I think is a perfect meld of your background and so forth." So far so good. I took over the company. We were eight people. We're 47 today, fully remote. The company has grown kind of all of KPIs are up into the right. Our traffic is up 100%, our users are up, user growth as community is up 300%, and revenue's up 400%, so. Yeah, it's been a lot of fun, yeah.

[00:04:05]Matt H.: Nice. So since you came out, or since you've been part of the community for so long, how have you seen the Dribbble community change, because it was my understanding that it was invite only originally, and it was sort of a core group of designers that were wanting to show their work. Then it's morphed into what it is today, so where, from a business perspective, how has it changed since you've been on and over the course of the eight years?

[00:04:29]Zack Onisko: Yeah, so it's still invite only. The community was really borne out of our co-founder. Dan Cederholm was writing a lot of books on web design and speaking in a lot of conferences, and he was really leaning over the shoulders of people at these conferences and saying, "Wow, that looks really cool. What are you working on?" That's really kind of the inception of Dribbble was this premise of being able to share what you're working on with a handful of designers. It was a closed community to start, just kind of a handful of top designers. Then the opened it up to the world via an invite system, and that was really just because Dan and Rich, the co-founders, were really just the two of them for many years. They were growing the business, so they had to be mindful of server bills and things like this.

[00:05:22] So it was partly to kind of restrict growth and then partly was quality control, right? They just wanted to make sure that the company, the platform had a high bar in terms of the quality of work that was being shared. That's still true today. It's been this exclusive community for a long time, which has been great for the people inside, but for the people not inside, we have designers all over the world now. They might not know somebody in their personal network to be able to invite them to Dribbble. So we're starting to look at ways that we can move away from an exclusive community and be more inclusive as we grow and mature. Part of that is looking at our invite algorithms, how we can be more inclusive to geographies that are not representative today. Then also just by working on partnerships with different organizations who have populations of designers who are not necessarily familiar with the Dribbble brand yet. For instance, design conferences in other countries or design schools. Things like this.

[00:06:33]Matt H.: Nice. Yeah, so it seems like what's so unique about Dribbble from my perspective is it has a long history and it still has the reputation, a very high reputation amongst the community that maybe other sort of forum style communities online haven't been able to sort of maintain. It seems like everybody still points to Dribbble, even though given your growth, things can potentially dilute, I guess, is the right word in terms of the quality and that sort of thing. So it's been really cool to see Dribbble maintain that. So how have you been able to do that outside of typical quality control?

[00:07:06]Zack Onisko: Yeah, so the way we're looking at it today is that we want to solve quality control with technology and not by people gating. There's just a ton of amazing designers, like literally hundreds of thousands of amazing designers out there doing really interesting work, and there's a ton of designers who are doing lesser quality work, but a platform like ours has the ability through social signals to be able to rise the good work and bring that work to the homepage so it gets more exposure regardless of if you've been on the platform for ten years and have 400,000 followers or if you're brand new to the platform and have 400 followers.

[00:07:47] So that's really the effort, how we're looking at the future is kind of this evolution and how do we grow the community. The community itself, like we have an internal kind of north star mantra, and it's that we'll be successful as a platform and as a community and as a business if we help designers become successful. So a lot of our focus over the past year has been around work opportunities and getting freelancers leads for projects, helping designers who are looking for full-time gigs get gigs. That's really delivering just a ton of value back to the community, and in turn, that's fueled out growth.

[00:08:25] As we look to the future, we're very interested in investing in education with hundreds of thousands upon millions of up and coming designers visiting the site every month. Today, unless you have an invite, there's not really a product for you on Dribbble other than an inspiration destination. So we want to look at, okay, how can we help these designers get jobs, right? How do they get the education to at least get the baseline so they can start to grow and become better designers over time? There's a design shortage right now, so we're in a very interesting time where technology has flattened the competitive landscape, and it's more easy than ever before to be able to start a new business and compete globally.

[00:09:07] The change, just as kind of a quick case study, there were about 150 SAS products in the martech space five, six years ago. Today, there's over 7,000. So as a consumer, as a business owner, to look at that landscape of potential marketing solutions, like its paradox of choice is super real, right? There's just all these different, discrete products. So the way that business owners are now looking at how they differentiate and how they compete in the market is by building better products, a better user experience, and that all stems in design. The old adage was just go throw more engineers at your product and build more features, and today it's really about just let's build a better product that will attract customers and retain them from leaving to go to a competitor that could have feature parity with your product.

[00:09:56] So really, companies are looking to win on customer experience and quality. We've seen this in Silicon Valley for years, right? Dropbox and Airbnb and Lyft really doubling down and building this design centric culture, but now we're starting to see this in Fortune 500. We're starting to see this across all industries, not just the Apples or the Nikes who you think are design led on within the F500, but companies like McDonalds and Kohls and Ford Motor Company.

[00:10:26] A great case study to illustrate the change in demand is IBM, old big blue, which you might envision being kind of a cube farm and they're actually innovating at a crazy pace. The ratio of engineer to designer at IBM has changed in the last five years from 72 engineers for every one designer to now it's eight engineers for every one designer. On their mobile teams, it's actually 3:1. So they're making mass investments, and we're seeing this kind of all across the landscape. There's just not enough designers in the market to facilitate the need. People used to talk about this demand problem and now there's companies who are raising their series A series B and a design manager has basically 20 job openings that they need to fill, and they just have difficulty finding talent.

[00:11:13] So anyway, to kind of backtrack, so education is definitely a huge focus for us as we move forward, because we see that there's a lot of ambition, people who are very interested in design. There's just a lack of education and training available at a professional level.

[00:11:29]Matt H.: Right. Right now, it seems like Dribbble is in a pretty unique situation to be able to offer those education resources given your region and given who is already on the platform. What would be the typical channel of a designer that wants to get the education and professional resources that you mentioned right now? Is that available easily for these people, or is it sort of, whether they go through the typical channels?

[00:11:53]Zack Onisko: Yeah, I mean, there's design schools, right? That's the typical path that you go down. You go and you spend 50k a year to go to one of these top design schools, RISD, Parsons. These are great schools, but not everyone can afford it. Not everyone is in the states. There's quite a bit of barrier to entry for a mass population to be able to get access to this education, this kind of baseline education for the craft. So yeah, so that's where we see a big opportunity for us is if we can help facilitate that and bring this skillset to a much wider audience.

[00:12:29]Matt H.: Interesting. I think just to circle back, so you mentioned that Dribbble is fully remote for the team. Is that correct?

[00:12:36]Zack Onisko: Yeah, yep.

[00:12:36]Matt H.: Nice. So for you, were you working remotely in your previous job, or is this the first one?

[00:12:42]Zack Onisko: So I have, right? So to go back to when I was running growth marketing at Creative Market, we had part of the team in San Francisco. I'm born and raised in San Francisco, so just as the nature of the beast of so many companies being here, I just didn't have the ambition to work remote. I think going back to early days, like the mid 90s, there's this Sandra Bullock movie, The Net. She's like hacking on the beach, and I'm like, oh, she's like in her bathing suit and with her laptop open. I'm like, "That's what working on the internet is like!"

[00:13:14]Matt H.: That's the dream.

[00:13:14]Zack Onisko: But fast forward to reality, my last job at Hired, I was commuting two hours a day. I have a young family, so we moved out into the suburbs, so I was taking the train in to San Francisco every day. I had to work ten hours at the office, and then commute back home. So I was literally leaving the house before my kids were awake and coming home after they'd gone to bed. I just wasn't seeing my family during the workday. So that bummed me out. When I was at Hired, we were a 280 person team. There were about 100 people in San Francisco and the rest of the team was spread out all over the world in 17 different cities.

[00:13:56] Of the people I managed in San Francisco, I would get people hitting me up every day saying, "Hey, can I work from home? Can I work from the coffee shop? Hey, I don't want to commute to work today." My stance was, we hire great people. We do great work. As long as you get your work down, I don't care if you work from the office or from the beach. That was kind of my stance on it, and it worked really well. It was kind of just this trust in our employees and they got the work done.

[00:14:24] Of the folks who were in the office, the funny thing is is that there's a limited supply of conference rooms, and everyone has meetings all throughout the day. So we'd fight to get into these rooms and then we'd just flip open our laptops and hop on Zoom to talk to our remote workers. So it's funny. I mean, we were playing six figures a month for rent. Hired shared the same building with Uber and Square, so super expensive. So when I joined Dribbble, the team of eight were all remote, and so I had just done a remodel on my house and built out a home office, which I'm in right now.

[00:15:02]Matt H.: Yeah, it looks great.

[00:15:03]Zack Onisko: Yeah, thank you. I have a bunch of guitars here, like you have behind you. Kind of just built my perfect little work den, and the original plan was oh, this is gonna be a place where I would work a day a week as I commute to the city the rest of the time. So when I joined Dribbble, I'm like, you know what? Let's just do this remote thing. I'm friends with the team at Envision, the team at Automatic, and I saw them successfully grow their 100% remote teams into over 500 employees nearing like 1,000 employees now. For me, it was a huge mitigation of risk, right? If these companies can do it successfully, if they can figure it out, we can figure it out too.

[00:15:49] So that was a pretty big decision early on. I think when I first joined, I was like, okay, should we get a WeWork? Then we started throwing some job reqs up and started to get these really great applicants from all over the place. So it just kind of snowballed. It was kind of on purpose and kind of accidental, to be honest, but we started to hire some really great people from all over. We had some folks in Canada, in BC, so we spun up a Canadian entity and we have a US entity, so I payrolled both countries. We literally had people spread out all over North America. We have a developer in the UK as well.

[00:16:31] So we started to get folks coming in, and also coming from just areas that weren't super expensive to live in. You can live off of a national average salary, right? Our pay is actually very competitive. We're in this, everyone's kind of between the 75th and 90th percentile, but way less than hiring people from San Francisco and New York who demand 3x national averages. So it's given us this freedom and (inaudible) we don't have this crazy, two and a half million dollar lease on a fancy office space in San Francisco. That goes back to our bottom line, and it's allowed us to build a fast growing, profitable, and bootstrapped business.

[00:17:23]Matt H.: Yeah. Something that I've come across quite often with companies that are starting out fully remote is that it wasn't necessarily their intention to go remote right off the bat. It was something that just sort of came naturally as you mentioned with the realization that there's all these benefits that come with having remote workers and just create a pool of applicants to pull from and this talent that wouldn't necessarily come across your plate.

[00:17:44] So that's definitely a trend. Is there an area of remote work that you've had difficulties with in terms of team building? Is there some separation between the fully remote team and people that are in an office together, and how has that affected sort of the culture building at Dribbble?

[00:18:01]Zack Onisko: Yeah, no, not to pat ourselves on the back too much, but we haven't had too much pain, mostly because we've gone in eyes wide open from the get go. So from the early team, we started to instrument kind of best practices in management, operations, organizational dynamics, these kind of management one on one stuff. Things like we weekly one on ones, so every direct report has a one one with their manager. No one feels like they're on a lonely island. They're not out of the loop in communication.

[00:18:36] One of the things that we saw fall down at my last company was that because there were 100 people in San Francisco, there were a lot of decisions being made, a lot of communication was happening that was going undocumented, and the remote folks were just out of the loop. So they're hearing about this stuff secondhand, and they're like, "Okay, well, why wasn't my voice being heard? Why wasn't I part of this decision?" Or "Why wasn't I even told this thing happened with the company that's this major thing?" So kind of learning from that experience, we knew we didn't want to do a hybrid approach. We wanted to go completely, 100%, and that was gonna force us to, one is to over-communicate, and two, and to over-document.

[00:19:16] So like I said, we do weekly one on ones. We do a team call, like an all hands call weekly, which gives every functional team an opportunity to do a deep dive into what they've been working on that week. We try to focus in on actual, visual demos of the feature versus going into bullet points where people can zone out and space out if they're not familiar with the project. So that's really brought us together as a company. At the end of that call, we open it up for personal stories. We just leave 15 minutes at the end of this call just for us all to interact as a team and as people.

[00:19:51] We have also evolved our culture a bit. We really want to invest, because we don't have these crazy line items in our P&L, we can reinvest that back into the team and do some really fun things for culture. Our perks, our Canadian employees, we do an upgrade on benefits. With the US folks, we try to have some of the best plans out there. We pay for most plans 100% of not only the employee, but their entire family's medical/dental. We have three month maternity leave. So there's some interesting things to do, education funds, gym funds, coffee funds. There's a bunch of cool things we do just to kind of make sure that people are comfortable in their job.

[00:20:31] But one of the interesting things we did recently is that we invested in a conference, and the idea here is that we knew we wanted to have FaceTime. As a remote company, we wanted to get together at least twice a year to just hang out and be able to bond as people in the same locale. So we made up a design conference, and it's called Hang Time. We bring in some of the top design leaders in the world to come share their stories and give workshops. We travel to a different city each time, and so we get the chance to invite the local community out to experience the conference, but also to meet our entire team, because the conference actually covers the T&E expense to fly out and put everyone up in hotels for a week.

[00:21:17]Matt H.: Nice.

[00:21:18]Zack Onisko: So that's an interesting thing that we do that's been a side effect of going fully remote.

[00:21:24]Matt H.: One of the things that I wanted to ask you about was as a fully remote team, how has the hiring process changed for Dribbble or evolved as a fully remote team? Do you look for something specifically in the people that you hire that you wouldn't normally look for elsewhere?

[00:21:40]Zack Onisko: Yeah, we do. So we try to screen for obviously skill set. We try to find people who are A players, top of their game, functional experts. We have a really high bar for culture, so it's a cliché of the no asshole rule, but we're kind of silly and goofy. We make a lot of puns and dad jokes and a lot of crazy emojis and gifs and that kind of stuff. It just makes work fun and so we want to find people who have that similar spirit. We look for people who have an affinity for the design community or have a creative background of some sort. A lot of us are musicians or have come from some other type of arts background, which just kind of helps you just hit the ground running and just understand our mission and our vision for what we're trying to build here.

[00:22:30] The fourth thing is really just trying to weed out people who just aren't geared for remote work. We've only made a couple hiring mistakes, pulling people out of big companies where there's just a lot of, you come to work and you sit around, you do a lot of meetings and you play a lot of politics, and that's really the job is, in some of these larger organizations. For us, we're a startup. We're still a roll up your sleeves, get shit done type of an organization, so that type of vein doesn't really work in a remote environment or really any small company environment, but especially a remote, right? It's just a huge red flag culturally when you see just see people not pulling their weight.

[00:23:19] So we're really just trying to find, trying to suss out that. We also want to suss out people who are just naturally just not into remote. There's kind of two types of people. There's people who working from home, they're like 3x more efficient and effective than if they were at a desk. In Silicon Valley, the wisdom is to have this open office with all the desks are doors on filing cabinets, and everyone, it's just this sea of people of clatter and people working. But if you go to one of these offices, everyone's wearing noise canceling headphones and they're just desperately just trying to focus on their work without being interrupted by their peers.

[00:24:00] So we believe that's kind of a broken model, but there's a lot of people, they just need to be around people and in an office to be able to get work done. So we try to avoid those hires. They're people who, when they work from home, they can't help themselves, but they have to, they get distracted by the sunshine or they have to turn on the TV or they have to go clean their house. That's just not gonna, that's not gonna work for us. We try to suss out for those types of signals.

[00:24:30]Matt H.: Right. Speaking of distractions and that sort of thing, is there anything that you do personally or you've seen sort of widespread across the Dribbblers to maintain focus and to make sure that they're in the most efficient workspace possible?

[00:24:41]Zack Onisko: Yeah, I mean, for a lot of us who are either former entrepreneurs, former founders, former freelancers, consultants, that type of experience, you're working solo a lot and you're responsible personally to get your job done. So the way we've structured the company is just, people have responsibilities and they sign up for work to be done, and it's really kind of up to that person to find their sweet spot, whether that's a coffee shop, whether that's their home office, their bed, or if they need to go to a WeWork.

[00:25:27] It just comes down to getting your work done. From our perspective, as a leadership team, the whole relationship's just built on a foundation of trust, and so if you have the skillset to do the job that you signed up to do, we trust you to go do it. If you don't do it, then we'll have a conversation about it, but for new people looking to work remote, to answer your question, I think it's really about finding your quiet place to be able to focus in and get good work done.

[00:25:59] We've also been very mindful of building best practices for Dribbble. I have an HBR subscription. I read all these best practices from other companies, but it rarely works where you can kind of copy and paste from somebody else. So we've been very mindful of trying to develop best practices for Dribbble and working remote at our company as we've grown. So a couple things we've been very mindful of. Time zone, so we try to get people as much overlap as possible. We try to hire, we try to solely hire in North America whenever possible so that we maximize the overlap, right? There's about a three hour gap between east coast and west coast. We ask our east coast folks to, if they can, can they start later in the day? We ask our west coast folks to start early in the day, just to maximize the overlap.

[00:26:56] What we don't want and where we see inefficiencies is if we have people working odd hours and someone on the team just can't get ahold of somebody and there's a whole day, 24 hour cycle passes before a project is unblocked. That's just an inefficient way to work. Another way is that we've, what we've been very mindful of is meetings and the number of meetings people are in. That's just a huge time suck, and so we developed a couple rules internally. One is that we have a no meeting Thursday and Friday policy. So that gives ICs time to go heads down and just focus on their work uninterrupted. People are free to close Slack and just go and plug in.

[00:27:42] The other thing we do is we have a no agenda, no meeting policy, and so that means that whoever's spinning up a meeting needs to write an agenda ahead of that meeting and share it with whoever they're inviting. There's time to actually do the research and dig into whatever decisions need to be made and to help minimize the amount of meetings that people have. So anyway, just kind of, these are just a couple examples of ways that we started to just evolve and come up with strategy for us to work more efficiently as a remote team.

[00:28:17]Matt H.: Did you find that when you first were starting to work remotely or when you first came on with Dribbble that there was a difficulty separating work from your private life? Was it just a matter of shutting off at a certain part of the day or turning off Slack or that sort of things? Was there a process that you had to put in place to make sure that people were getting their own time?

[00:28:37]Zack Onisko: So people are pretty good about it. I wish I was actually better at it. I'm self admitted a workaholic, and I have a hard time turning it off, but this year in particular, I've been better at, this is silly, but carving out time to eat. So actually taking a lunch break, and I take the dog for a walk. I carve out time at the end of the day to go to the gym and actually, and just having a routine pulls me out of work mode and gets me to think about other things. But most days, around 6:00 o'clock when my family kind of comes home is when I turn everything off and like to spend at least a few hours with my wife. Helping my wife in the kitchen and helping the kids get ready for bed and all that stuff. Baths and that's super important to me. Then yeah, usually after the kids go to bed I hop back on online and do a couple more hours.

[00:29:38] But for the most part, the team's really good about that work/life balance. One thing that we also have is just, again, just built on this foundation of trust. We provide everyone with a pretty flexible ability to plan their day however they choose. So we have no strict hours where you need to be in seat. We've had an employee who went half time to travel around in her van and live in her van for six months and camped and spent half of her day working and half of her day rock climbing.

[00:30:17]Matt H.: Nice.

[00:30:17]Zack Onisko: That was her jam. We have another employee who is a coach for his kids' sports teams, so he typically logs off at 3:00, goes and does that a couple days a week, and then comes back and makes up some time at the end of the day. So we want to provide these opportunities for people. It's a luxury of life to work remote, really. We can actually take our kids to the doctor or go get groceries or go do normal life stuff whenever, at a moment's notice. So that's cool.

[00:30:49] We also want to make sure that people are always kind of recharged and have time to do great work and aren't burning out. So we have an unlimited PTO policy. People can take extended vacations and come back and we just ask the people to do great work and we're pretty open and flexible outside of that.

[00:31:09]Matt H.: Yeah, it sounds like for you, and I think for a lot of other fully remote teams, it really comes down to trusting your employees and the people that you work with to be able to get their work done.

[00:31:19]Zack Onisko: I mean, it's the way it should be, right? I mean, if I'm a manager in an office, there's no guarantee that just because somebody's sitting at a desk that they're doing work. Most of my employees at my last company were just spending most of their day on Facebook and Twitter anyway, so.

[00:31:33]Matt H.: Yeah. So within the community of leaders in tech, it seems like it's definitely moving in the direction of sort of being open to remote work and flexible work and that sort of thing. Is there a common thread or a common theme of reasons why you wouldn't within the CEO and tech leadership community? What's something that you hear a lot for that?

[00:31:54]Zack Onisko: Yeah, I think there's a lot of knee jerk reaction from investors, and from the mindset of an investor, they're just looking for a return on their investment at some point in the future. A lot of these funds are seven, ten years and they have to pay back to the investors in those funds. So the way that these portfolios are built are positioned to flip these companies and sell them to larger acquirers. I think the fear with investors is Google or Apple or Facebook, are they gonna want to acquire a remote team or are they only gonna want to acquire teams that are willing to move to Mountain View?

[00:32:43]Matt H.: Right. Interesting.

[00:32:45]Zack Onisko: So I think that's the big hesitation is really coming from the venture world. For us being bootstrapped, it's just not a problem. We have the investors, and so again, the landscape is quickly shifting. The ease to be able to start a company is becoming more and more easy and efficient to get something off the ground. So I think the entrepreneurial landscape is gonna shift as well, and less companies are gonna require seed funds and angel funds to get something going and more people will be able to work with talented people all over the world and not have to move to companies, to San Francisco to attend YC or whatever.

[00:33:34]Matt H.: Right. It seems like something that I hear or come across quite often is that fear but in a different context of more aligned with how do I know my people are working when they should be working? How do I know? It just seems like it's more difficult to micromanage a fully remote team, and maybe I'm wrong in that, but it seems like that's something that people fear of letting go at least of the control a little bit there.

[00:34:01]Zack Onisko: Yeah, honestly, I think that's just an immature management mindset. To be honest, I think any seasoned manager, you have goals that are set. You have milestones. You have weekly sprints. You have daily standups. It's really easy to see if work's not getting done or not.

[00:34:23]Matt H.: Right, of course. Yeah, yeah.

[00:34:26]Zack Onisko: So again, it's about hiring great people who are great at their functional skillset and just trusting people to do great work and do it on their terms and it works out.

[00:34:37]Matt H.: Right, now what would you say to somebody who is maybe going to transition or is starting a company and wants to go remote or is part of a leadership team that maybe are thinking about considering remote work. What would you say would be something that you would want to start right away as your team disperses in terms of processes and practices and things like that?

[00:35:00]Zack Onisko: I mean, I would say focus on efficiencies and unblocking inefficiencies. So kind of starting at the bare basics. Time zone is gonna be the big one. With Slack and Google Docs and Zoom, those tools would help facilitate some of the blockers that people complained about years ago. So it's much easier to get set up and running off the bat. Then it's really just about common tools for working as a web company, right? It's project management. It's Asana or JIRA or whatever your flavor is. It's having some kind of realtime collaboration, so chat, whether that's Slack or HipChat or whatever your jam is.

[00:35:55] So anyway, there's all these tools, and that really is the biggest, that has been the biggest roadblock, I think, historically from allowing, except for bandwidth, right? To allow this type of work to happen. So I think that when you're small, there's just not a whole lot of process needed. There's not a whole lot of heavy lifting needed to get this going and to work effectively. As you grow and the teams get bigger, then you just need to lay down some best practices and processes, but we take a very light stroke to those sorts of things.

[00:36:42] But it just keeps people on the same page. What you don't want is people feeling like they're out of the loop or not plugged into what's happening, so it just comes back to over-communication, over-documenting, just doing a great job of bringing the team together.

[00:36:56]Matt H.: Yeah, and I think one of the things that you mentioned before that's super important is to try to make sure that you're getting the conversational interactions that aren't necessarily related to work and just making sure that you have that as a priority, your people and you work at a company and just to make sure that that's a priority. Because I think that kind of gets lost a little bit sometimes when you're only communicating about work related things. A lot of that stuff can get forgotten about, which I think is important.

[00:37:25]Zack Onisko: Yeah, I mean, culturally for us, we try to prioritize fun. We try to prioritize a sense of humor and just keep work as light as possible. We have Chloe who heads up our people ops. She runs virtual happy hours, virtual book clubs, virtual movie clubs, virtual book exchanges. So we try to do a lot of fun stuff. We do remote gaming.

[00:37:52]Matt H.: Oh really? Nice.

[00:37:53]Zack Onisko: Role playing games, so yeah, there's just different ways that we try to connect and have fun. We're not over Zoom and video chat. Then that kind of fills the blanks before we get to see each other in person twice a year for Hang Time. That work is really kind of laptops down. We just spend a week just hanging out and eating and drinking, going to museums together, that sort of thing.

[00:38:18]Matt H.: Nice. I can attest to the Dribbble team's use of emojis and things like that. Over Slack, you guys are real experts there, so kudos to you.

[00:38:29]Zack Onisko: Thank you, thank you.

[00:38:29]Matt H.: So I want to be cognizant of your time, Zack, and I really appreciate you being here with us today. I have a couple more closing questions for you. You kind of touched on one of them, but what is your favorite tool that you use for remote work, and you can take it in any direction you want to.

[00:38:47]Zack Onisko: It's emoji, definitely.

[00:38:49]Matt H.: Of course, that's right. I knew the answer already.

[00:38:52]Zack Onisko: No, I mean, we're really big into Slack and Zoom, of course, but we use Bonusly, which is a plugin for Slack. We award each other points that can then be cashed out. Dribbbpoints, all one word. Three Bs. They can be cashed out for various things, whether it's Amazon gift cards or if you want to actually donate your points to charities. So the team really enjoys that. It's a lot of fun. We use a daily standup plugin for Slack that I am spacing on the name of right now. Is there a robot in it? Anyway-

[00:39:32]Matt H.: Yeah, I think I know what you're talking about.

[00:39:33]Zack Onisko: I'm drawing a blank, yeah. Sorry. But yeah, so we look at things like that just helps automate a lot of processes and make work a little more fun.

[00:39:43]Matt H.: Nice. So my last question here for you is not related to work. What is your favorite unplugged activity?

[00:39:52]Zack Onisko: Well, I do have some acoustics, but most of the time I plug in.

[00:39:56]Matt H.: Oh yeah.

[00:39:57]Zack Onisko: I like to turn up my amp here in my office and piss off my neighbors at least once a day. I don't play any bands anymore, but just kind of fiddling around helps release a lot of tension and helps me relax.

[00:40:11]Matt H.: For sure.

[00:40:11]Zack Onisko: Outside of that, it's just really just dad mode, taking the kids to soccer or ballet or whatever is super rewarding for me.

[00:40:18]Matt H.: Nice. Well Zack, I really appreciate this. This is, I think, a pretty successful first recording of the show, so thank you so much for being here and we really appreciate it.

[00:40:26]Zack Onisko: Yeah, thanks for having me.

[00:40:31]Matt H.: Thanks.

[00:40:31] Thank you so much for listening to the show today. Check out for the newest career opportunities and so you can start your remote work journey. We're looking for guests on the show, so if you have someone in mind you think we should talk to, please send us an email at That's Also if you have any tips and feedback, we welcome that as well. Just be nice, because this is my first time, so go easy.

[00:40:59] Also make sure to follow us on Twitter, Facebook, and LinkedIn as well, and thanks again for listening.

Key points in this episode