So, you’ve been cruising along in the VP of Engineering seat for a while. You’ve delivered projects, built teams, and earned credibility. And now you’re eyeing the big chair: CTO.
How do you actually make the leap?
It’s not easy. A CTO slot is one of the most competitive executive positions out there. But with the right mindset, you can dramatically improve your odds of getting hired.
For the rest of this discussion, let’s assume you’re actively applying for CTO roles and you want to tilt the odds in your favor.
The “Winning Bet” Strategy
There’s a key strategy I’ve used in the past called “winning bet” & it massively increases the likelihood you’ll snag the CTO spot.
The essence of this strategy is understanding that every company is making a certain kind of bet when they hire a CTO, and therefore you should position yourself as the “winning bet” in order to get the job.
This framing alone will separate you from 90% of the VP-level candidates who walk into interviews focused only on their résumé or technical depth.
How Companies Make CTO Hiring Decisions
Let’s get something straight: companies don’t hire CTOs with a spreadsheet full of weighted scores.
Sure, there are variables they talk about, usually 10 to 20 of them, but the actual decision is messy, intuitive, and full of tradeoffs.
Here are the most common factors that come up when boards, CEOs, or investors are evaluating a CTO candidate:
Compensation expectations
Technical depth and credibility
Breadth of leadership experience
Fit with the company’s future roadmap (what needs to get done in the next 12–24 months)
Cultural alignment
Ability to attract and retain top engineering talent
Ability to build and scale a high-performance team
Track record of fixing big problems (security, technical debt, outages, etc.)
Communication and board presence
Most companies ping-pong between these different factors as they make the decision.
One day it might be all about your experience. The next it might be a comp-based decision.
What seems to be common with CTO hiring is highly intuitive & instinct-based decisions.
Juggling Tradeoffs
If you’ve never been on the other side of the table, here’s what it feels like inside those hiring discussions:
Conversation 1: “Her comp is reasonable, but she’s never worked in our industry.”
Conversation 2: “He’s brilliant technically, but he burned out at his last role.”
Conversation 3: “She could definitely do the job, but we need to settle on the CEO first.”
That’s what it looks like. Back-and-forth, constantly juggling tradeoffs, trying to land on the candidate that feels like the least risky bet.
At any given time, you’re being compared on 3–5 variables. Some days you’re up, some days you’re down.
This is why interviews can feel inconsistent.
One day they grill you on experience, the next they only want to talk about technical debt. The truth is, they’re hedging their bets continuously in real time.
The Opening
If you’re a VP of Engineering gunning for a CTO role, here’s the truth you need to internalize: the hiring process isn’t logical. It’s not fair. And it’s not purely about skills.
Companies don’t hire CTOs like they hire engineers.
When they’re hiring an engineering manager, the conversation is: Can this person manage a team, deliver features, keep the trains running?
When they’re hiring a CTO, the conversation shifts entirely:
Can this person be the face of technology for the company?
Will investors trust them?
Will the CEO rely on them?
Will they create leverage or destroy it?
This is a completely different level of scrutiny. Every part of your background, your presence, and even your personality becomes part of the bet.
Think about it from the company’s perspective:
They might be sitting on $50M of capital that hinges on hitting product milestones.
Or they’re a PE-backed company with a two-year clock to clean up tech debt and drive towards an exit.
Or they’re a founder-led startup where the board is demanding more maturity in engineering leadership.
In each case, the CTO isn’t just a leader, they’re the linchpin for whether the business creates or destroys value over the next 24 months.
That’s why these decisions feel so emotional, even chaotic. The company knows they’re betting the business on whoever they pick.
And that’s your opening.
Because if you understand the psychology behind the decision: how boards, CEOs, and investors juggle risk then you can position yourself as the highest-upside bet they can make.
Positioning Yourself as the Winning Bet
Companies generally think of hiring CTOs as making a bet.
Sometimes companies bet risky: taking a flyer on a first-time CTO who’s raw but brilliant.
Sometimes they bet conservative: bringing in a seasoned executive with scars, a safe pair of hands who won’t break anything.
But make no mistake, at your comp, they’re betting that you will create more value than you cost.
Think about it like this:
A venture-backed startup with two years of runway doesn’t want a safe “steady state” CTO. They’re betting on speed, disruption, and someone who can scale.
A PE-backed roll-up drowning in legacy tech debt doesn’t want a flashy product visionary. They’re betting on a fixer who can stabilize systems, cut costs, and rebuild credibility with customers.
A Fortune 500 subsidiary trying to modernize its stack doesn’t want a gunslinger. They’re betting on political savvy, enterprise process, and someone who can navigate stakeholders.
In each case, the winning bet looks completely different.
This is where most VP candidates stumble. They show up pitching their résumé instead of positioning themselves as the answer to the company’s actual bet.
Your job is to:
Understand the nature of the bet. What is this company really solving for in the next 24 months? Growth? Stability? Cost discipline? Innovation? Governance?
Align your story to that bet. Highlight the specific parts of your track record that de-risk their biggest fears.
Frame your comp as leverage. Not as a cost, but as a multiple on value creation.
If you can walk into the process and make the board, CEO, or investors see you as the candidate that matches the bet they’re already inclined to make, you instantly separate yourself from the pack.
This is where you stop being “a qualified VP who wants the job” and start being “the obvious CTO pick we’d be crazy not to hire.”
Closing Thoughts
Breaking into the CTO seat isn’t about being the smartest engineer in the room, or the most accomplished VP. It’s about understanding the psychology of the people making the decision.
Every board, CEO, or investor hiring a CTO knows they’re making a bet. A bet that you’ll not only solve today’s problems but also carry the company through the next chapter of growth, stability, or transformation.
Most candidates fail because they treat the process like a résumé contest.
They throw their experience on the table and hope it matches whatever the company is looking for. That’s passive. And it leaves your fate up to the chaos of internal debates, shifting priorities, and tradeoffs you’ll never hear about.
The candidates who win, the ones who actually get the CTO title, flip the equation.
They:
Recognize the bet the company is making.
Frame their background as the winning answer to that bet.
De-risk the doubts and tradeoffs that derail less prepared candidates.
Position their comp as a value-creation multiple, not a line-item cost.
Here’s the shift I want you to walk away with:
Stop thinking of yourself as applying for a job. Start thinking of yourself as offering a bet.
Because at the end of the day, that’s what the company is buying. Not your résumé. Not your years in the trenches. Not even your technical depth.
They’re buying a bet that you’ll be the leader who makes their next two years easier, safer, and more valuable than the alternative.
If you can internalize that and walk into the process positioned as the obvious, highest-upside bet then you’re not just a candidate anymore.
You’re the CTO they’ve already decided they need.
By the way, reach out for help if you need it: bobby@technocratic.io.
Bobby, thank you for the article! This is a true story of making decisions not only for CTOs, but for many other senior-level positions. I was always thinking that every hiring process has two sides: objective (skills and achievements assessment) and subjective (making a bet). The higher the level of the role, the more importance is given to the subjective side.
Thanks Bobby for another great, diverse article. Understanding CTO selection from the other side of the table as a 'Winning or best available Bet' is going to be one of the best levers which anyone can use. Also your explanation of different strokes for different business types( start up, PE, steady state enterprises etc) helps a CTO aspirant avoid wasting time pursuing a low percentage of success job application.