Executive AI Coaching

1:1 coaching for ambitious, impact-focused leaders who want a peer you can borrow -- someone who's been at the frontier and is here to show them the ropes. We figure out together what's worth building, where agentic AI fits in your work and life, and how to stay current as the world keeps changing.

Most ambitious leaders I sit down with already know agentic AI matters. They've heard the case. They've read the right newsletters and watched the right keynotes. They're a little tired of frameworks, and they don't have time to figure it out alone. What they want is someone who's actually built with these tools -- Claude Code in particular -- to sit next to them in their real work and life, and help them put it to use in a way that actually compounds. So that's what we do. You bring something real. We turn it into something that runs -- a personal AI Command Center that knows your priorities, a workflow that gives you back hours every week, something only you would have thought to make.

How the work goes

What we actually build

A few of the things leaders have walked out with from a single session.

A sounding board for the bigger AI questions

Beyond the building, I'm a thought partner for the strategic AI questions in your org and the broader landscape. What's worth investing in. What to ignore. What this means for your team. How to talk about it without overpromising or underselling. Part of my job is to stay at the frontier so you don't have to spend hours every week trying to keep up. The AI for Business certificate from my MBA and a lot of experience using these tools gives me an outside perspective leaders often appreciate.

Who this is for

Ambitious, impact-focused leaders who want to do more of the work they love, and less of the work that isn't theirs. The common thread is leaders in transformation moments who already know AI matters and want a knowledgeable thought partner who can sit with them in the actual work.

Looking for something beyond 1:1? I also run small group activations for executive teams and longer embedded residencies. Reach out if that's the shape you're after.

Who I am

Colton Hess

I'm Colton. I just finished my MBA at Berkeley Haas and am now finishing my MPH at the UC Berkeley School of Public Health. I was in the inaugural cohort of Berkeley's AI for Business certificate, one of the first AI-focused MBA programs in the country. I have experience as a founder myself, and a deep respect for what it takes to lead an organization in a rapidly changing world.

More on the about page →  ยท  LinkedIn →

“
I had no idea what was possible with Claude Code until working with Colton. I'm now overwhelmed with possible ways to create and build tools that can upgrade my personal and professional life.
-- Catherine, Startup Founder

Questions leaders ask

What is AI coaching for executives and founders?
AI coaching for executives and founders is ongoing, hands-on, 1:1 work with another founder who's actually built with these tools. You bring real work and together we turn it into something that runs with agentic AI like Claude Code... a personal command center, a workflow that gives back hours. You stay in the driver's seat with the judgment and the taste; I bring the AI fluency and the hands. I can also be a sounding board for your org-wide AI strategy, not just 1:1 skill-building. Think of it as a peer you borrow.
How much does AI coaching or AI consulting cost?
It always starts with a free intro conversation, because I'd rather make sure it's a real fit before we talk about anything else. Activation Playbook is built to be more accessible than the usual options: a fractional Chief AI Officer or a big consultancy can run well into five or six figures, and that's overkill for most founders and teams. This is fit-first instead. We start with what you're actually trying to build, make sure it's the right match, and size it to your engagement from there. Reach out and we'll figure it out together.
What's the difference between done-for-you and done-with-you AI?
Done-for-you AI means a consultant builds the thing and hands it over... you get an artifact, but not the ability to change it. Done-with-you AI means we build it together, in the room, so you own both the result and the muscle memory. That's what Activation Playbook is: nothing gets handed off. We work on your real project with Claude Code from the first hour, and when I step back you can keep building without me. The whole point is that you grow your own sense of agency, not a dependency on me.
How is AI coaching different from a fractional Chief AI Officer?
My AI coaching is the lighter, more accessible alternative to a fractional Chief AI Officer. A fractional Chief AI Officer fills an interim executive role and owns decisions for you. I do the opposite: I sit alongside you while the work is growing, then step back, so you grow your own sense of agency and don't outsource it. It's a peer you borrow, not a seat on your org chart. Working through AI in your own role makes you the more grounded, forward-leaning leader the moment is asking for.
Do you offer Claude Code coaching or training for non-technical leaders?
Yes, I offer Claude Code coaching and training built specifically for non-technical leaders. Claude Code is the primary tool in my 1:1 Executive AI Coaching, used not as a coding skill but as a way to orchestrate AI in plain English to ship real artifacts... dashboards, workflows, internal tools, board memos in your own voice. Most leaders I work with arrive with a working command of Claude or ChatGPT and want to move past the chat window. And this isn't only for business: I can help you use AI better in your personal life too.

Engage

If this sounds like the right shape, the easiest first step is a short call or a note. No deck on the other end -- just a conversation about what you'd want to build.

Book an Activation Consultation Or write me