Companies usually start to look for a VPE/CTO at Series A/B, and it is one of the highest-leverage decisions you’ll make. It’s also one of the easiest to get wrong.
Not because there aren’t strong candidates, but because most companies aren’t honest with themselves about what they’re actually hiring for. And then everyone is surprised a couple months later when things aren’t working.
This post is about getting that clarity before you run a single interview.
1. Figure Out What You Actually Need Right Now
Before you hire a VPE/CTO, you need to answer a hard question:
What problem are you trying to solve today — not in two years?
Common needs I see:
- You need reliable execution and delivery
- You need strong technical direction and architecture
- You need org building: managers, hiring loops, process, structure
You might not actually need a VP of Engineering yet. False negatives are extremely costly and you need to minimize risk as much as possible. I’ve found this post from Laura Hilton at BCV to be much better at providing you a field guide than anything I could write.
You should think about what would happen if you hired a strong line manager that has managed 10-15 people and could drive execution and processes. Maybe you end up still owning org structure. You could leave room to layer in a VP/CTO or this high potential EM could surprise you and rise to the challenge. I’m not saying this is the right path forward, but you should consider every possible solution before deciding on hiring a VPE/CTO, and this is usually an option that people don’t evaluate.
2. Expectation Setting: You’re Probably Hiring For Multiple Jobs
At early-stage startups, most VP of Engineering / CTO roles are not a single job.
You’re usually asking this person to:
- Be deeply hands-on technically
- Own architecture and systems design
- Hire aggressively
- Manage and grow the team
That’s a staff engineer, a VPE, and a recruiter. People who can and want to actually do that will expect to be compensated accordingly. Most likely, this type of person is going to be intrinsically motivated and view compensation through the lens of respect vs an absolute number. Most companies don’t have the long-term scope or vision to justify this level of effort or to drive enough interest to attract top candidates. Be realistic.
Be upfront about:
- How hands-on you expect them to be right now, in 6 months, and in a year
- In-office expectations: 996? Always available for incidents?
- What “crunch” realistically looks like and how long do you expect to be in that state
- How much ownership and autonomy they actually have: Do they have to check every decision with you?
- What is the comp range for this role? You really don’t want to get all the way through the offsite and then be completely off on numbers.
People have always tried to hide this stuff. For a role this senior and this impactful, hiding it is how you fail the hire before they even start. Given that AI has kept teams significantly leaner, it seems like VPEs are expected to be much more hands-on than they would’ve in the past.
3. Make Sure Your Team Is Actually Ready
This hire isn’t just about technology. It’s about people.
A VPE/CTO is going to:
- Take over management of your team
- Change how decisions get made
- Introduce new standards and expectations
If your existing team isn’t aligned on that, you’re setting everyone up for failure. It isn’t just you hiring this person, it’s your entire team. Obviously you can’t have every single person interview every candidate but you want to get as many different people exposed to your top candidates to ferret out any potential issues.
4. There Are Very Few Truly Great (Early Stage) CTOs
There are not many people in the world who are truly great CTOs. Not because people aren’t smart, but because the job requires a rare combination of skills that are usually developed separately across different stages of companies.
The role demands:
- Deep technical judgment
- Execution under extreme ambiguity
- Hiring and talent evaluation
- People leadership and coaching
Many strong candidates will be uneven across these dimensions. In one moment you need to be deep down in the weeds and in another you need to be up in the clouds talking with investors, executives, etc.
The real question isn’t:
“Do they have every skill today?”
It’s:
“Which risks am I willing to take? Which am I not?”
Someone who is technically elite and execution-focused may not have had many reps building org structure or formal hiring processes. Someone who is a great org builder may not have shipped critical systems themselves recently.
You need to be honest about what you can support, what you can teach, and where failure would be unacceptable.
Conclusion
Everything above is about what you’re hiring for, and whether you should be hiring this role at all.
In Part 2, I’ll cover what attributes a strong CTO would have. Finally, in Part 3, I’ll discuss how to assess them and some tips on running a professional process.
Hiring this role well can change the trajectory of your company. Hiring it poorly is incredibly hard to unwind.
Clarity is the first step!
The Gambler 
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