How to become a CTO?

When you messaged me last Thursday, if I’m not mixing up my calendar invites — you asked a deceptively simple question: “What does it actually take to end up in the CTO chair?” I’ve been turning that question over on my dog-walks ever since, because, frankly, the path looks neat only in hindsight.

My own route was half-strategy, half-fluke. I’d been a senior backend dev for barely a year when the Head of Development quit after a blow-up with the CFO (long story involving CAPEX budgets and ego). I scheduled five marathon meetings — think three hours each, lots of bad coffee — and convinced management to hand me the keys. Right place, right time, equal parts stubborn and naive. I still call it luck, though some colleagues insist it was “initiative.”

The promotion felt glamorous for about a week, and then the imposter syndrome showed up with moving boxes. I knew how to optimize queries; I had zero clue how to set a hiring plan or defend a roadmap in front of the board. A few months later I co-founded mindnow and grabbed the technical helm there, which amplified the learning curve even further. I’m not sure this sequence is copy-pasteable, but we can tilt the odds in your favor.

First, the role itself. Once the org passes, say, 30 engineers, “CTO” turns into a business job wearing a tech hoodie. Budgets, politics, P&L — then only after that comes architecture. You’re the person signing off on multi-year commitments, negotiating cloud spend, and explaining why feature X is late without throwing your team under the bus. Code still matters, but mostly as currency for credibility.

✅ Remember one thing — the job of a CTO is to build People Systems that build other Systems, ideally without your hands on the keyboard.

The softer bits — hiring, firing, saying “no” nicely — are where careers stall. I’d start a checklist:

1. Make reversible decisions fast and irreversible ones slowly.
2. Hire people who can out-argue you (and then listen).
3. Practice delivering bad news without spiraling into excuses.
4. Block off weekly focus time; context switching will eat you alive.

I could be wrong, but mastering those four moves beats another certificate on Udemy. Still, a bit of structured learning never hurts. An MBA module on finance or a crash course in org psychology will give you vocabulary for boardrooms — I binged Coursera videos at 1.5× speed during my commute; good enough.

Inside your current gig, grab anything that forces accountability: cross-team projects, vendor negotiations, rescue missions for failing features. The scar tissue from those efforts is what investors quietly look for when they whisper, “We need a technical co-founder who’s seen some things.” (Side note: document wins and losses; you’ll need stories later.)

Be cautious with shiny C-titles at tiny startups. Founders sometimes hand them out in lieu of cash. Check runway, vesting terms, and whether you’re the real C-suite or just leading a two-person dev pod reporting to a VP Product. I’ve watched more than a few “founding CTOs” get side-lined after a Series A when investors parachuted in a grey-haired replacement. Negotiate board-level visibility or single-trigger acceleration before you print new business cards.

You’ll rarely slide into a CTO job through a public posting. Searches happen quietly: reference calls, back-channel LinkedIn messages, forwarded résumés over Signal. Visibility helps, politics helps more. So yes, network — even if, like me, you’d rather refactor CSS than small-talk. Host an internal tech brownbag but invite external speakers; attend two conferences a year and ask questions from the mic. The goal is simple: when someone mentions “We need a CTO,” your name should pop up in the next sentence.

Mentorship speeds things up. Find one person two steps ahead — not ten — who’s willing to be candid over espresso. I meet my mentor roughly every quarter; the agenda looks like “What am I missing?” and “Which hill should I die on this year?” Rarely comfortable, always useful.

Public presence comes last. Blog, OSS, podcasts — they compound, but slowly. I wrote into the void for almost two years before a single inbound lead showed up. Keep at it if you enjoy writing; skip it if you don’t. Authentic beats obligatory content calendars every time.

✅ CTO compensation swings wildly with risk, runway, and how indispensable the board thinks you are.

Money talk: expect anything from low five figures (pre-seed, ramen runway) to mid six figures plus stock at profitable scale-ups. The spread is ridiculous. I once met a 24-year-old “CTO” making a low salary who lost both title and salary bump once the company raised. Build protections into your contract: vesting cliffs, severance, advisory shares — boring paperwork that future-proofs your mortgage payments.

The job is stressful — sometimes thrilling, often lonely. Schedule downtime like a doctor’s appointment. I block Wednesday evenings for climbing; non-negotiable. Burnout doesn’t care about your ambitions, and a fried CTO is a liability to everyone.

Ping me whenever. Happy to sanity-check offers, swap war stories, or just complain about vendor lock-in.

Enjoy the ride — bumps and all.