You’re at 15 engineers. Maybe 20. The CTO is making architecture decisions, running 1-on-1s, managing the sprint process, interviewing candidates, dealing with the board’s technical questions, and still somehow trying to think about what your platform needs to look like in two years. Something is going to break. It’s probably already breaking.

The answer isn’t to hire faster. The answer is to separate the management of engineering from the technical strategy of engineering. That’s what a VP of Engineering does. And this is one of the most consequential hires you’ll make, because the wrong person doesn’t just fail — they damage the team they manage, and recovery takes 12 to 24 months.

What a VP of Engineering Actually Does

Before you write a job description, get clear on the job. A VP of Engineering is not a super-senior engineer. They are an organizational leader whose primary output is a high-functioning engineering team.

Concretely, that means:

  • Hiring, onboarding, and developing engineers at every level
  • Performance management — including the hard conversations
  • Process design: sprint cadence, code review standards, incident response, on-call rotations
  • Cross-functional coordination with product, design, and sales
  • Translating business priorities into engineering capacity and sequencing
  • Keeping the team informed, engaged, and productive while the CTO sets technical direction

Notice what’s not on that list: making architecture decisions, setting the technical roadmap, or being the most technically brilliant person in the room. That’s still the CTO’s job. If you need the VP to do those things too, you need a different conversation about your CTO.

What Separates Strong Candidates from Impressive Resumes

Every VP of Engineering candidate will tell you they’re a servant leader, they love building teams, and they’ve scaled engineering organizations. Here’s how to actually tell the difference.

Ask about someone they had to let go. The best VPs I’ve seen can give you a detailed, unsentimental account of a performance management situation — how they identified the problem, how they handled the conversation, how they made the decision, and what they’d do differently. Weak candidates give vague answers (“it didn’t work out”), over-philosophize about the humanity of it, or have never actually fired anyone.

Ask how they’ve handled a conflict between a senior engineer and a product manager. This is the daily work of the job. You want to hear someone who navigated it with specificity, not someone who says they “bring people together.”

Ask what their 30-60-90 day plan would be. Strong candidates will talk about listening before changing, auditing processes before proposing replacements, and building relationships with the existing team before asserting authority. Candidates who show up wanting to immediately implement the processes they used at their last job are a risk — they’re replicating rather than diagnosing.

Ask about a time engineering and business were misaligned. You’re looking for someone who can hold both sides accountable — who doesn’t just become an advocate for engineering to business, or a translator who defends business to engineering, but who can create actual alignment. This is harder than it sounds and most candidates haven’t done it well.

The Traps

Don’t promote the best senior engineer. I’ve watched this go badly more times than I can count. Great engineers who haven’t explicitly managed people before often lack the emotional toolkit for the role. More importantly, you’ll take your best technical contributor offline for 6-12 months while they figure out management — and if it doesn’t work, you lose both the manager and often the engineer.

Don’t hire someone who needs to be the smartest technical person in the room. Your senior engineers will test this. If your VP needs to prove technical credibility by winning arguments, you’ll have a culture problem fast. The best VPs I’ve seen are genuinely comfortable saying “I don’t know — what do you think?” to senior engineers and then holding them accountable for the outcome.

Don’t skip the reference calls. Call references that weren’t provided. Call people who reported to the candidate, not just their former managers. Ask “what would the people who worked for them say about them?” — not “would you recommend them?” The latter is almost always yes. The former tells you something real.

Don’t underprice the role and expect to get someone good. VP of Engineering at a 15-20 person engineering team is a $200K–$280K role in most markets. If you’re offering $160K because “it’s a startup,” you will get someone who couldn’t get the better-paying job.

The Specific Question to Ask Your CTO

Before you post the job description, have a candid conversation with your CTO about where the line is. What decisions does the CTO retain? What decisions does the VP own? What happens when they disagree?

If your CTO can’t answer these questions clearly, or seems uncomfortable with the VP having real authority over team management, you have a different problem — a CTO who isn’t ready to delegate. Fix that first, or your VP hire will fail regardless of how good the candidate is.


If you’re at the stage where you’re thinking about this hire, the framing questions usually matter as much as the candidate evaluation. In a 15-minute call, I can help you think through what the role should look like for your specific situation and what the most important questions are for your first round of interviews. Book a free 15-min call.


Related: Hiring Your First Engineering Leader | How to Evaluate CTO Candidates | Fractional CTO vs VP Engineering