How to Hire Your First VP of Engineering
The most consequential technical hire a founder makes, and the one with the least reliable interview signal.

The failure mode is nearly always stage mismatch. A leader who was excellent at a hundred and fifty engineers is frequently wrong at twenty, and the interview process rarely surfaces this because both parties are discussing the same words.
Define the next eighteen months, not the title
- Is this a building problem or a scaling problem?
- How much of the role is hands-on?
- Who owns technical architecture after they join?
- What does the org chart look like at the end?
Reference properly
For leadership hires, references from people who reported to the candidate are worth more than references from people they reported to. Ask about retention and about what got worse under their leadership.


