How my role as CTO has changed as we've grown to 100 engineers

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  • 1 engineer: 12-14 hours a day coding, woohoo
  • 2-10 engineers: 60% coding ,40% hiring. Player-coach
  • 11-50 engineers: At this point, I believe technical co-founders have a binary choice: Stay on the technical track and hire a professional manager (usually given the VP of Engineering title), or give up coding and focus on the management aspects yourself. It really isn’t possible to do both.
  • By the time we reached around 50 engineers, I was spending 60% of my time being the best manager I possibly could to my direct reports, and training other engineering managers in the team to do the same. The remaining 40% of my time was spent recruiting.
  • My enjoyment now comes less from the things I do myself and more from the impact that I helped others to have.