Executive AI coaching for CEOs
A five-time CEO and executive coach for chief executives leading their companies through the AI era. The work spans the whole business: strategy, people, hiring, pricing, board, competitive position, backed by hands-on AI fluency most coaches don't have. Not tool training. Judgment, from someone who has sat in your chair.
“Our calls are the highest leverage time on my calendar.”
Niall O'Malley · CEO, eTraining
What is executive AI coaching?
Executive AI coaching is one-to-one coaching for a chief executive on leading their company through AI. It pairs the judgment of a seasoned executive coach with hands-on AI fluency, so a CEO can think through the decisions AI forces at the top: strategy and competitive position, how AI reshapes people and talent, what to adopt and what to ignore, and how to lead the organization through the change. Unlike training, it is not about building tool skills. It is about leading well while the technology is reshaping the business.
When the CEO owns it, the results aren't close.
realize meaningful business value from AI
are confident in their AI strategy
report established ROI from AI
Yet only 24% of organizations put the CEO in that seat.
Source: KPMG Global AI Pulse, Q2 2026.
Who is this coaching for?
This coaching is for chief executives who intend to lead AI themselves, not delegate it. Most fit one of four situations:
The CEO repositioning the company around AI
Built the company pre-AI, now absorbing it without losing what made the business work.
The multi-time founder
Been in the chair before, back in it again, and the technology moved while they were heads-down.
The board-facing CEO
Every board meeting opens with AI and every investor call closes with it; they want to think it through before they have to say it out loud.
The leader of an established business
Mature company, mature market, suddenly novel competition; they want to lead the response, not be led by it.
What do we actually work on?
We work across five domains, in no fixed order, starting wherever the pressure is right now and moving as your priorities do.
Strategy
What AI means for your business, your moat, your next moves.
People
Team design, talent shifts, leading through transition.
Technology
What to adopt, what to ignore, what to build.
Change
Managing the organization through the transformation.
Outcomes
What success looks like and how we measure it.
The landscape shifts monthly, so the thinking has to stay current. We maintain living analyses like our comparison of ChatGPT and Claude for organizations (opens in a new tab), and we bring that same freshness to every decision we work through together.
Who is the coach?
Kevin Williams is an executive coach and five-time CEO, and the founder of AscendAI. He has coached CEOs and senior leaders for years, since well before the current AI wave, on the real work of running a company: strategy, people, pricing, and the hard calls.
What sets his coaching apart now is that he is also a daily AI builder. He has launched four commercial LLM-based products and exited a prior company to private equity, and he can pressure-test a hiring decision and then walk you through an agent architecture in the same conversation. He advises boards, public-company executives, and state and federal lawmakers on absorbing AI without losing the company in the process, one client at a time.
Advisor, Utah Governor's Office of AI Policy · Co-chair, Responsible AI Initiative, University of Utah · Cited in The Wall Street Journal, Financial Times, Inc.
What do CEOs say about working with Kevin?
I've leaned on Kevin as a sounding board for running my business for years, long before AI was the thing everyone talked about. What sets him apart is that he's equally strong on both sides: he can pressure-test a hiring decision or a pricing model, and then walk me through agent architectures in the same conversation without missing a beat. And it's because he is a builder and operator himself, in the trenches like me, and has been for a long time. He knows my business well enough to challenge me (and he's thankfully not afraid to!) and knows AI thoroughly, so I trust him on his technical perspective too. He's talked me out of bad ideas, sharpened good ones, and more than once saved me months of time by steering me away from unnecessary rabbit holes. Our monthly calls are the highest-leverage time on my calendar.
Niall O'Malley · CEO, eTraining
I can't imagine a better executive coach for a moment like this than Kevin. The current pace of disruption demands an understanding that goes well beyond the headlines. Kevin sees where the disruption is heading and constantly challenges me to look farther afield. He understands what cutting edge technology is doing and helps cut through the hype and noise. Even more remarkable is that Kevin understands and cares about people. Leading with a balance of vision and compassion is not an easy thing to do, and Kevin helps me walk that line.
Steven Low · President, KLAS Research
Working with Kevin over the past three years has been transformative at every level, from high-level strategy down to the operational details of how our business actually runs. He knows our people, our clients, and our real challenges, and he consistently asks the right questions to surface solutions that actually stick. His expertise in AI has been especially valuable, helping me think through both the frameworks and the practical, hands-on ways to integrate it into our company. I can't recommend Kevin highly enough. He's an exceptional coach and a genuine partner in building a better business and building me into a better leader.
Common questions
Is this only about AI, or broader business coaching?
It is broader. Kevin is an executive coach and operator first, working across the whole business — strategy, people, hiring, pricing, and the hard calls a CEO has to make. AI is the differentiator he brings that most coaches can't, not the limit of the work. Many clients start on an AI-shaped problem and quickly find the conversation is about running the company well.
How is this different from a regular executive coach?
Most executive coaches are not operators, and almost none build with AI daily. Kevin is a five-time CEO who does both, so he can pressure-test a business decision and then work through the underlying technology in the same conversation. You get strategic coaching and current, hands-on AI judgment from one person.
How is this different from your personal AI coaching?
Personal coaching builds your own AI fluency, privately and one-to-one. Executive AI coaching is about leading the company through AI — the strategy, people, and organizational decisions at the top. Some leaders do both; they answer different questions.
How is this different from hiring a consulting firm?
A consulting firm sends a team to produce a deliverable and then leaves. This is an ongoing, one-to-one relationship with a single operator who stays in the work with you. There is no deck handed off and no associate doing the thinking; the engagement is built around your judgment as the CEO.
How do I get started?
Start with the Snapshot: a short, private assessment that takes about five minutes and gives you a tailored set of AI practices calibrated to how you actually work. If there is a fit, we follow up privately.
How do I start?
A short, private assessment — five minutes, no strings. You'll leave with a tailored set of AI practices calibrated to how you actually work. If there's a fit, we'll be in touch privately.
