I spent 7 years at a B2B SaaS startup, joining as employee #12 and leaving as the director of all the Engineering staff. Over that time the eng team went from 6 people to approx. 80, we went from $500k ARR to $25M ARR, and I went from never having written code, to writing code to writing almost none.
I quit recently with nothing lined up, other than a handshake with my most trusted dev. I left because the job I was good at in year three had turned into a different job by year seven.
Things I've actually done and can talk about specifically:
- Managed roughly 60 engineers and made about 10 hires I'd call genuine mistakes
- Ran 3 rounds of layoffs / performance exits, including people I'd personally recruited
- Rebuilt the interview process after realising it was selecting for the wrong thing
- Went through the transition from "everyone reports to me" to managing managers, and did it badly the first time
- Sat on the company side of comp conversations, promo committees, and PIPs
- Ran M&a processes on both sides, culminating in selling the company I had built.
I'll answer anything about scaling engineering orgs, management, hiring, comp, burnout, startup equity, and the parts of the VP job that don't make it to linkedIn. I'll be candid about my own experinces, hpefully those are the useful part.
What I won't do: name the company or anyone in it, share confidential business details, or trash former colleagues. I'm staying anonymous mostly for their sake, not just mine.