I've spent much of my career as a public company CEO and, more recently, as a senior leadership coach. Throughout that journey, I've been fascinated by two questions: What do leaders need to get done and how do they go about doing it, especially under pressure. Over the past several years, I've worked extensively with founders and executives building. AI-enabled businesses while simultaneously exploring whether frontier AI models could genuinely support leadership thinking. Not in a generic, motivational way, but in the real, messy situations leaders face every day.
At the same time, my long-time colleague and friend, George Tolomiczenko, brought decades of experience in behavioral science, clinical psychology, public health and applied research. Together, we began exploring whether advances in AI could be combined with rigorous behavioral insight to create something genuinely useful for senior leaders.
The result is CEOJester.
Part leadership laboratory, part behavioral science experiment, and part AI platform, CEOJester is designed to help leaders think more clearly, challenge assumptions, identify blind spots and make better decisions under pressure.
Associate was the first product in what we expect will be a multi-generation platform. What we learned from Associate is now informing the development of Partner and Founder.
It’s good at brainstorming, surfacing options, and pressure-testing your thinking. Occasionally, like a bright associate, it needs to be reminded to slow down and not get ahead of itself — and it’s been trained accordingly.
Associate is especially effective when used in conjunction with your behavioural data, helping you spot:
likely blind spots
predictable stress reactions
and common failure modes before they show up in the room
If you’re:
stepping into a new leadership role
fine-tuning your strategy
dealing with a difficult performance issue
re-shaping your team
navigating board misalignment
working through a product launch
managing post-acquisition integration
or any of the countless ambiguous situations senior leaders face, Associate is available to help you think clearly, challenge assumptions, and stay out of your own way.
It’s not a replacement for human judgment.It’s a thinking partner that’s always available.
Why “the Jester”?
In medieval courts, the jester served a unique function. In an environment where honest feedback to the king could cost you your head, the jester was one of the few who could speak truth, often through humour, without punishment.
CEO Jester carries that same spirit.
It’s designed to offer candid reflection, surface uncomfortable patterns, and challenge your thinking, while never taking itself too seriously.
