Ok now that some time has gone by I can reflect a bit more thoughtfully here.

My top mistakes as a SaaS founder/CEO:

  1. Not convincing the very, very, very best VPE I knew to join as our VPE. I tried and I tried for years. But looking back, I should have tried even harder. I should have camped in his office and literally never taken No for an answer. It would have solved our top problems and been a game-changer. I had a great CTO, but I also needed a truly great VPE to scale past $10m ARR and deal with all those issues. I’m 100% confident we’d be running a multi-billion dollar public company together if I’d closed him.
  2. Overreacting to competitive threats. We were growing 100% at $10m ARR, with 120% NRR. Respecting the competition is critical, but worrying too much can hurt you. They couldn’t stop us, even if they could maim us a bit.  More here.
  3. Not seeing other chances would come. We had a few tough hits with one strategic partner, and lost a few big deals. That seemed like such a huge deal, and at the moment, it was. But we got more chances later on.
  4. Not finding a way to work through team conflicts better. Our CTO was amazing, but we didn’t work together as well as we should of. In some ways, it was a different time. But while I used all the tools I knew to have a better relationship, I should have done more.
  5. Not raising a bit more money. We did fine, and got cash-flow positive by $5m ARR. But I could have done a lot more with just a bit more money.
  6. Not becoming a better recruiter.  I recruited a great VP of Sales, a strong VP of Marketing, a great VP of Product (now COO at Gong), and a great VP of Customer Success.  And most of the team was great.  But I was a sequential recruiter.  I should have been recruiting more great folks, more often.  More here.
  7.  Not staffing up partnerships and biz dev better.  The best product doesn’t win on its own, even if it gets you in the door. Once you build a partnership, you need a small army to maintain and scale it. To get to know not just the CEO or a VP, but the 50+ folks that work under them. To make every SE and AE your champion, too.
  8. Not visiting even more customers in person. We got pretty good at this later, but I should have done a lot more of it, a lot earlier. When I looked back, we never lost a customer under my watch that I visited in person.
  9. Not competing more in spaces where we were weaker.  This is nuanced and complicated, but we won tons of deals, thanks to a great sales team and an easier-to-use product, with our core ICPs. Tech, insurance, web professionals, etc. But we didn’t even bother to try to win in verticals where we were less competitive. This makes sense in the earlier days, since its far more efficient to play where you win a lot. But as you scale, you also want to play where you win just “sometimes”. There’s a lot of TAM there. And your product evolves.

(tough ones image from here)

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