As we approached $10m ARR, we were doing very well. But I did see that certain of my weaknesses still were impacting how well we could do:
- I didn’t get on enough jets. I didn’t visit enough of our biggest customers in person. The ones I did visit, we never lose. More here: I Never Lost a Customer I Actually Visited | SaaStr
- I remained a serial recruiter. You have to move to parallel recruiting. I was too slow in recruiting VPs, and only did it one VP at a time. You have to become a parallel recruiter by $2m-$3m ARR or so. More here: How Get Better at Recruiting. (We All Need To). | SaaStr
- I needed to do better at Biz Dev follow-up. I was very good at initial partnerships and biz dev, but less good at all the details in following up in the months and years to come. I should have built out a true Biz Dev function as soon as we had a handful of partners to manage.
- I thought an IPO would take like forever. I was right in that it would be many years off, but I was wrong in that that was OK. It is supposed to take a while in SaaS.
- I worried too much about dilution. I had scar tissue from too much dilution in my first startup, so I swung the pendulum too far the other way. We only spend about $6m net to get to $10m in ARR and became cash flow positive at $4m ARR. That was great, but having too tight of a balance sheet inhibits some investments. I should have just raised another $20m and not worried about the dilution. More here: Don’t Worry About Losing All Your Investors’ Money | SaaStr
Having said all that, I was also too acutely aware of my weakness. All the above could have been solved with a few key hires. I should have worried less about my weaknesses, and just used that energy to go make an extra hire.
Take a pause and just go make those key hires.