Executive Coaching
A trusted partner with no agenda
What is executive coaching?
Executive coaching for a CTO, VP of Engineering or founders is a standing one-on-one partnership — a weekly or bi-weekly session focused on org structure, delivery health, hard people calls and technical strategy, with async access between sessions. Engagements are rolling with no fixed end date, and completely confidential.
For technical leaders
Current or aspiring CTOs, VPs of Engineering, and engineering leads
Whether you're stepping into the role for the first time or facing new complexity as you scale, the technical part was never the hard part. It's the shift from writing the code to owning the outcome — from being the person with the answers to being the person who builds a team that has them. I work with you week to week as a partner in the calls that come with that shift: org structure, delivery, hard people calls, and technical strategy.
For startup founders
Founders and CEOs running an early-stage company
You carry decisions across the whole business, often without a peer to think them through with. I'm in your corner for the hard calls — the exec hire you're unsure about, the co-founder friction, knowing when to push and when to hold. And when a problem is half people and half technology, as most of them are, I'm one of the few who can read both sides at once.
No company is like your company
Your company isn't a case study, a maturity model, or a checklist. It has its own market pressure, personalities, constraints, history, and ambitions. What worked for another startup—or even for you at a previous company—won't map cleanly. Treating it like it should is how smart teams end up stuck.
So the work isn't handing you a playbook. It's understanding your context first, then bringing experience, patterns, and judgment to bear on the decision actually in front of you — with clear thinking and honest tradeoffs, grounded in your reality.
Range from doing, not just coaching
The range that counts doesn't come from advising a lot of companies. It comes from operating inside them. Hiring calls that went well and ones that didn't, architecture bets, missed quarters, the recovery plan after.
That changes the advice. It's more concrete, more honest about the constraints you're actually under, more aware of what breaks downstream. The goal isn't to be prescriptive — it's to help you make a call that still holds when the meeting ends and the pressure's still there.
How we work together
The role
Coaching is a one-on-one partnership. I'm in your corner week to week — a trusted, independent thinking partner who helps you pressure-test decisions, work through hard situations, and spot the blind spots you can't see from inside the company.
Cadence & commitment
- A standing weekly or bi-weekly one-on-one session
- Async access between sessions for the calls that can't wait
- A rolling engagement — no fixed end date, continue while it's valuable
- Completely confidential
How it unfolds
We work from what's live for you right now — an org decision, a key hire, a board conversation, a technical bet — and pressure-test it together: I bring what I've seen play out, you bring what's true for your team. Exploring every angle so you can commit to the call instead of second-guessing it.
"Ian has been an invaluable technical advisor and steadying force for me as a founder. He combines strong engineering judgment with rare emotional intelligence - helping me make better technical and product decisions while staying focused, grounded, and clear through the uncertainty of building an early-stage company."
"Ian helped TrueNorth (Series B startup) level-up its engineering power. Within the first months, Ian was able to take this young team from being months behind on the roadmap to a team that consistently delivered work on time."
"Our outsourced team was months behind schedule and continuously delivering buggy code. Ian helped us identify different team structure options, and facilitating a clear plan of action that got us back on track and improved the quality of our deliveries."
"After shipping a new data product, Shareaholic faced rising monthly infrastructure costs. By migrating development languages and re-architecting our data serving systems, Ian helped us achieved an 80% cost reduction and a 5X capacity increase."
What does executive coaching cover?
Whatever is live for you right now — an org decision, a key hire, a board conversation, a technical bet. Sessions work from a real situation rather than a curriculum: you bring what is true for your team, and we pressure-test it against what has played out elsewhere, so you can commit to the call instead of second-guessing it.
How often are the sessions?
A standing weekly or bi-weekly one-on-one, plus async access between sessions for the calls that cannot wait. It is a rolling engagement with no fixed end date, continuing while it is valuable.
Is it confidential?
Completely. That is the point of an independent partner with no agenda — no stake in your board, your team politics, or the outcome of any particular decision.
How is coaching different from advising or consulting?
An advisor gives you an answer and a consultant delivers a piece of work. Coaching builds your own judgment on the decisions you will keep facing after the engagement ends. The range comes from having done the job rather than only studied it, so the conversation can go technical when the problem is technical.
Who is executive coaching for?
Technical leaders — CTOs, VPs of Engineering, heads of engineering — and startup founders carrying technology decisions with no peer to test them against. It suits people whose leadership playbook worked at the last stage and has stopped scaling at this one.
Coaching builds your judgment on the calls you keep facing. If what the company needs is someone to own the technology decisions outright rather than think them through with you, that is fractional CTO work — and if the pressure is a technical leadership hire you have never had to assess, that is leadership hiring.
You don't need to figure it out alone
A short call to talk through what you're weighing right now — and whether I'm the right person to think it through with
Let's talk