We've been involved in CTO hiring from every angle. We've been the fractional CTO who helps a founder write the job description, design the interview process, and evaluate candidates. We've been the CTO candidate being evaluated. And we've inherited the consequences of CTO hires that went wrong.
Hiring your first CTO is one of the highest-leverage decisions you'll make as a founder. Get it right and you have a technical partner who turns your vision into something real. Get it wrong and you'll spend a year and a significant chunk of your funding before the damage becomes clear.
Here's what we've learned about what to actually look for.
The five things that matter
Have they shipped something real?
This is the single most important question and the first one we ask. Not "do they know React or Kubernetes." Not "did they work at a big tech company." Have they built a product that real users depended on and pushed it through the messy, unglamorous process of getting it to production?
Shipping is an entirely different skill from coding. It requires making tradeoffs under pressure. It means cutting scope when the timeline is real. It means dealing with edge cases that nobody considered during the design phase. It means making something work reliably for people who don't care about the technology underneath it.
We've seen candidates with incredibly impressive resumes who have never actually shipped anything. They've worked on features within large systems at big companies. They've built prototypes and proofs of concept. But they've never owned the whole journey from zero to production, and that gap shows up fast when they're responsible for a startup's entire technical output.
The red flag is when candidates talk about technologies more than products. If someone spends 20 minutes explaining their Kafka expertise and zero minutes explaining what they built with it, that tells you something.
Can they communicate with non-technical people?
A CTO who can't explain technical concepts to a non-technical founder will make decisions in a black box. You'll find out what they decided after the code is written, not before. And by then, changing course is expensive.
You need someone who can explain architecture decisions in business terms. Not "we should use a message queue for event processing" but "right now, when a customer places an order, they wait four seconds while the system sends emails and updates inventory. If we process those in the background, the order confirmation is instant and the system handles failure more gracefully."
You need someone who can translate timelines into commitments you can plan around. Not "it depends" (which is always technically true) but "if we cut the analytics dashboard, this ships in six weeks. If we keep it, eight weeks. Here's why."
And you need someone who can say "no" to your feature requests with a clear rationale. Not "no, that's hard" but "we could build that, but it adds three weeks and creates an ongoing maintenance burden. Here's a simpler version that tests the same hypothesis."
If you want to test this in an interview, ask the candidate to explain a past technical decision to you as if you were a stakeholder. If you can't follow the explanation, they can't do this part of the job.
Do they think in systems?
Great CTOs don't just solve the immediate problem. They ask what happens next.
If this feature succeeds, what breaks at 10x scale? What's the simplest version of this that tests the hypothesis? What's the cost of getting this wrong? What are we coupling together that we'll want to separate later?
This is the difference between a senior developer and a CTO. A senior developer builds the feature you asked for. A CTO asks whether it's the right feature to build, how it fits into the bigger picture, and what second-order effects it creates.
The red flag is candidates who jump straight to implementation without asking about constraints and context. If you describe a feature and they immediately start talking about which framework to use, they're thinking like an engineer, not a technical leader. That's not necessarily bad, but it's not the CTO function.
Can they hire?
Your CTO will need to build a team. That means writing job descriptions that attract the right candidates. Running interviews that actually evaluate relevant skills. Selling people on joining an early-stage company when they have offers from established ones. And most importantly, evaluating technical talent accurately.
This is harder than most founders realize. A lot of engineering interviews test trivial knowledge (algorithm puzzles, obscure language features) rather than practical ability. A good CTO designs an interview process that evaluates whether someone can ship quality code in a team environment, handle ambiguity, and debug real-world problems.
Ask CTO candidates how they'd structure an interview process for a senior engineer. The answer tells you a lot about their hiring judgment.
Are they honest about what they don't know?
Technology moves fast. Nobody knows everything. The best CTOs we've worked with are the ones who say "I haven't worked with that technology, but here's how I'd evaluate whether it's right for us" rather than faking expertise.
The red flag is candidates who have a strong opinion about every technology, framework, and approach. That's not expertise. That's either arrogance or insecurity. Both are expensive in a CTO.
Three types to avoid
The resume CTO
Impressive credentials. Big tech companies. Maybe an advanced degree from a well-known program. But they've never built anything from zero. Enterprise engineering and startup engineering are different sports. The skills that make someone effective inside a team of 500 engineers at Google are not the same skills that make someone effective as the sole technical leader at a five-person startup.
This doesn't mean big-company experience is worthless. It means you need to look for evidence that they can operate in a completely different environment. Have they built a side project? Have they done any early-stage or consulting work? If their entire career has been inside large companies, the transition to startup CTO is rough and your company probably shouldn't be the experiment.
The yes CTO
They agree with everything you say. Every feature idea is great. Every timeline is achievable. Every concern you raise gets a reassuring answer.
This feels great during the interview and during the first month. Then reality shows up. Features slip. Quality drops. The CTO never pushed back on the things that needed pushback because they were optimizing for your approval, not your product's success.
You need a CTO who will tell you that your idea is technically feasible but strategically wrong. You need someone who will say "if we build that, it costs us three weeks on the feature that actually drives revenue." A CTO who agrees with you about everything is not a technical partner. They're an expensive employee.
The architecture astronaut
They want to build for a million users before you have a hundred. Three-layer caching strategy. Kubernetes cluster. Event-driven microservices. Automated canary deployments.
All of this is appropriate at certain scales. None of it is appropriate when you have 12 paying customers and are trying to figure out if the product even solves a real problem. We wrote about this pattern in detail in our post on why your SaaS MVP doesn't need microservices.
Over-engineering at the early stage is just as dangerous as under-engineering. It's just slower to kill you. Instead of your product breaking under load, your product never gets to load because all your engineering time went to infrastructure that nobody needed yet.
Full-time versus fractional: how to decide
You don't always need a full-time CTO on day one. Here's the honest breakdown.
Go full-time when your product is the business (not a tool supporting a service business), when you have funding and can offer competitive compensation, when you need someone writing code 40+ hours per week, and when you're ready to give meaningful equity in the range of 2% to 5%.
Go fractional when you're pre-product or pre-revenue, when you need strategic guidance more than daily coding, when you can't afford over $250,000 a year in salary, or when you want to test the CTO function before committing to a permanent hire.
A fractional CTO typically costs between $5,000 and $15,000 per month for 10 to 20 hours per week. That's enough to set your architecture, hire your first engineers, and make the build-versus-buy decisions that define your product's trajectory. We've written a detailed account of what a six-month fractional CTO engagement actually looks like if you want to see the week-by-week reality.
One common mistake: don't hire a CTO because investors told you to. Hire a CTO when you have a clear technical workload that requires strategic leadership. Otherwise, you're paying for a title, not a function.
The bottom line
Your first CTO sets the technical DNA of your company. They choose the stack, establish the engineering culture, and make decisions that compound for years.
Evaluate for judgment and communication, not just technical skill. Look for someone who has shipped real products, who can explain technical decisions to non-technical people, and who will push back on bad ideas. And if you're not ready for a full-time hire, a fractional engagement can give you the strategic guidance you need without the overhead you can't afford.
We help non-technical founders make confident technical decisions. If you're looking for your first CTO, or wondering if you need one at all, let's talk about it.