Career Direction: Startup v Enterprise
YOE: 9
After moving to the UK, I switched careers around 4 years ago. I've been at startups since, but now have enough experience that I've interviewed at some bigger names.
- Google – FSR role - All "hire" recs, great feedback, but they hired internally mid-cycle. No cooling-off period, so I can reapply, but need to network heavily
- Databricks – Greenfield AE - Clicked with the HM, he even advocated for me internally. Didn't clear the technical bar, but the recruiter said he was trying to place me elsewhere. I'm actively working on closing that technical gap.
- AWS – AE - Thought I did fine, but the HM had a strange demeanour. Kept asking if ChatGPT wrote my answers. (First of all, I use Claude... but anyway...)
The startup is at an interesting inflection point — we're just starting to generate real UK revenue, and I'm leading expansion into my home country's market, which also overlaps with my previous industry. The CEO tends to hire externally for leadership roles, so a promotion is unlikely. My development is entirely self-directed — we're all figuring it out for the first time. And because it's early stage, it's not a clean quota-carrying role.
I'm also implementing, doing plenty of role-adjacent work, and that at times makes it a harder story to tell in interviews with larger companies. BUT it is very flexible and I get lots of technical exposure & learning, which I'm enjoying. Equity isn't anything meaningful (apparently being reworked). I pushed for a market-rate salary adjustment a year ago and got 20-25% — not nothing, but now I know I can do better. And I'm flying economy and expensing my own meals on work trips, not ideal...half joking. It's the classic early-stage trap: all the responsibility, limited authority, unclear trajectory.
Google and Databricks would be either a 2x or 3X OTE bump. I have a young family and while I genuinely value the flexibility I have now — but I don't want to stay somewhere comfortable at the expense of my career trajectory.
So — as an employee, what's the move? Stay the course at a Seed/Series B and see it through, or jump to an enterprise company now?