Why Was Cloudflare's Restructuring So Hard?

Dane Knecht says the restructuring was hard, and saying goodbye to some colleagues was the first time Cloudflare ever did it. Cloudflare had always been careful not to overhire. The reason was different: AI was transforming how some teams work, so Cloudflare thought of the operation like a factory floor that had to be rebuilt and rethought.

A product manager sending an email to customers used to involve three teams. They went to BI for a cohort of people, to the marketing team to design the email and get the voice right, and to the marketing operations team to get the email out. Redesigning the process took hard changes that forced people to rethink the right way to do it, and the new path might not involve the three teams at all. What came out was a tool where a product manager describes the cohort and writes an email. The tool rewrites it in Cloudflare's voice, sends it to their manager, and the manager can click approve if they like it, and it goes up. Cloudflare did not make three teams faster at the old work. One tool lets a product manager know they have a superpower they did not have before.