My first 5 hires at Adobe Sign / EchoSign, beyond the core founding+ team, once we had paying customers and first, if early, product-marketing fit:
- #1: Full-time sales rep at $8k-ish MRR. I Should have hired two. Should have hired him even earlier. Hired once we were closing > 1 new, non self-service customer a week. More here:
- #2. A great, paid, full-time-ish intern. A great one is a terrific force multiplier. For me, a smart generalist that could be a force multiplier to get the things done I wanted to do myself but ran out of time for. A mini-me, I guess. If you can find one — hire them!
- #3: VP of Marketing. I hired at $20k MRR. Should have hired even earlier. Because “all” she had to do was improve our process and get us a few other good leads to pay for herself. More here.
- #4: Head of Customer Support — a veteran. I can’t believe I waited so long. This made our customers 50x happier, and I didn’t have to force everyone in the company to take so many shifts in support to help out the untrained resource(s) I had staffing it before. More here:
- #5: VP of Sales at $1.5m ARR-ish. I should have had 2 fully scaled reps first, not just 1. But in the end, it was the right time, I just needed someone that was a better fit for my product, ACV, and stage. A bit more here:
I should have hired them all, together, earlier. They were all accretive, so in the end I didn’t save any money by staggering the hires. Even if I felt the pressure of not running out of money.
I also waited way, way, way too long to hire into customer success. I had support do this at first. Rookie error.
And note we had 4 strong core engineers to start, so we didn’t hire any in the Next 5. (Perhaps we should have hired one more great one to build accretive features, though.)
(note: an updated SaaStr Classic answer)