Companies usually start to look for a VP/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.
That’s not because strong candidates are rare. It’s because most companies don’t define what problem they’re trying to solve with this hire. 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. What Do You Need Right Now?
Before you hire a VP/CTO, you need to answer a hard question:
What problem are you trying to solve today and what are you trying to solve in two years?
Common needs I see:
- Building an execution engine to ensure reliable and predictable delivery of features
- Defining a technical roadmap to scale to the next order of magnitude
- Building an org: processes for hiring, onboarding, career growth, reliability, etc.
This matters because the skills needed to fix those problems are not the same. Leaders who excel at organizational building may not excel at deep technical execution without support; vice versa is equally true.
Before you commit to a VP/CTO search, consider alternatives that might resolve your immediate risks:
- Could a strong line manager with 10-15 reports and a track record of delivery fix the execution problem? Maybe that’s ok for now? Maybe it isn’t.
- Maybe you end up still owning the org structure and layer in a VP/CTO in another year?
- Maybe the candidate rises to the occasion and is able to take this on.
- I’m not saying that this is necessarily the right solution, but it is often one that isn’t even discussed as an alternative.
- Could a senior tech lead or principal engineer drive architectural clarity and still ship code?
These alternatives are not inferior paths. They are different ways to solve the same problem with lower risk at early stages. False negatives are extremely costly and you ned to minimize risk as much as possible. I highly recommend this post from Laura Hilton at BCV to help guide you through this decision.
2. Expectation Setting: Multiple Jobs in One Title
At early-stage startups, VP/CTO roles are not single-purpose.
You are often asking the same person to:
- Be deeply hands-on technically
- Define and own architecture and systems design
- Build hiring processes and scale the team
- Develop people and formalize management
This bundle rarely exists in one individual. And people who can do most of this well expect to be compensated for it, not just materially but in autonomy and scope. The major failure case I’ve seen here is an unreasonable timeline to find this candidate. Also, you need to be honest with yourself on whether your company even has the long-term scope or vision to justify this sort of unicorn. I don’t mean that in a derogatory way but most companies are solving a small slice of problem both now in the future.
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?
- 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 onsite and then be completely off on numbers.
So much wasted time is due to a lack of clarity on expectations (from both sides). Be realistic with yourself and the candidates and be honest. It is hard to separate your inherent bias, so try and run through your requirements and expectations through friends or early candidates and refine it as you go.
3. Assess Whether Your Team Is Ready
A VP/CTO hire is about more than technical skill. It is about people and culture.
A VP/CTO is going to:
- Take over management of existing team members
- Change decision-making patterns
- Introduce new standards, norms, 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. You also need to very clearly define the expectations that your team has for this role as well. Some of it might be unreasonable, some of it might be good, but again the earlier in the process you uncover this, the less issues you’ll have down the line.
4. Truly Great Early Stage CTOs Are Rare
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:
- Technical judgment under ambiguity
- Execution drive without clear requirements
- Hiring and talent evaluation instincts
- People leadership at all levels
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, customers, etc.
The real question isn’t:
“Do they have every skill today?”
It’s:
“Which risks are we willing to take, and which must be mitigated”
For example:
- Someone excellent at org building may not be comfortable writing critical systems code themselves.
- Someone with elite technical and execution ability may need support in formalizing hiring systems.
You need to be honest about what you can support & 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.
Clarity about problems, expectations, team readiness, and risk tradeoffs is the first step toward a successful search.
In Part 2, I’ll cover the attributes of strong CTO candidates.
In Part 3, I’ll share how to assess them and run a professional process.
Hiring this role well can change the trajectory of your company. Hiring it poorly is incredibly hard to unwind.
The Gambler 
Leave a comment