You've been in the seat. The hard part didn't stop.
You're not looking for a guide. You're looking for someone who'll tell you what they actually think.
The problems that show up at year three are different from the ones at year one. You're not asking how any of this works anymore. You're asking whether the org you've built can survive the next stage. Whether the relationship with your CEO will hold under the pressure you can see coming. Whether a decision you're about to make is the right one, or the one that felt right last time and cost you eighteen months.
This is where a thinking partner matters differently. Not someone to explain the role — you know the role. Someone who's been in equivalent rooms, has no stake in the outcome, and will push back on your reasoning without a political agenda. That's what this engagement is.
What we work on
The problems nobody admits they're still working on at year three.
Not fundamentals. The harder, slower, more expensive problems — the ones where the feedback loop is long and the cost of getting it wrong is high.
- Org design at inflection points The structure that worked at 30 engineers breaks at 80. You need a leadership layer you didn't need before — which means hiring people who own things you used to own, and building relationships with them that are fundamentally different from the ones you had with engineers. How to do this without creating a bureaucracy, losing the technical edge, or spending twelve months hiring the wrong VP of Engineering.
- The CEO/CTO relationship at scale Three years in, the dynamic has calcified. You know each other's patterns. The board has opinions. The CEO's trust in you is based on a track record that was built at a different stage of the company. How to renegotiate the relationship without making it weird, maintain your authority when the company is being told by investors to "bring in experienced leadership," and stay aligned on a technical strategy your CEO can defend in rooms you're not in.
- Decisions with no playbook Replatforming a system that's under load. A make/buy/partner call where all three options have merit. An acquisition that brings a team with its own architecture and culture. These are decisions where your instinct is a data point, not an answer — and where working through the reasoning out loud with someone who has made comparable calls is worth more than any framework.
I've been a CTO at a funded startup, a VP at a large telco, and a founder three times. I've made the expensive versions of most of these mistakes, and I've also been in the room when they went right. I'm not going to tell you what to do. I'm going to help you think it through until you know what you actually think.
Weekly or fortnightly 1:1 calls · 6-month engagement · One spot currently available
Book a free 30-minute call →Also relevant: First-time CTO mentoring → · VP of Engineering mentoring → · Imposter syndrome at the CTO level →