Dear SaaStr: What Were The First Five Hires You Made After Product-Market Fit?

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)