AI Executive Roundtable

A Private, invitation only conversation for senior AI Leaders navigating complexity, scale and responsibility.

As a senior AI leader, you likely face challenges that few others fully understand.

You’re navigating strategic pressure, ethical uncertainty, organizational scale, and the human cost of velocity — all while trying to stay grounded in what matters.

This is not a workshop or a panel.

It’s a curated, confidential roundtable with 8–12 peers who are asking similar questions — and leading at similar altitudes.

Below are some common themes we might explore:

Leadership in the age of Agents

How do you lead when AI is not just a tool but an actor in decision-making?

What does agency look like across humans, models, and systems?

Strategic Misalignment

Where is the biggest disconnect between AI ambition and operational capacity?

How do you realign cross-functional teams around adaptive, not reactive, strategies?

Trust, Transparency, and Governance

What models of internal and external trust are emerging?

How are leaders building governance frameworks that do more than check boxes?

Scaling AI beyond pilots

How do you scale AI initiatives without compromising on ethics, trust, or long-term alignment?

What happens when the push for velocity outpaces organizational readiness?

AI Talent, Teams, and Culture

What’s changing in how AI teams are built, managed, and retained?

How do you cultivate creativity and resilience in a rapidly evolving AI workforce?

Human Development at Machine Speed

How do you lead human transformation (identity, behavior, mindset) as fast as the tech evolves?

What’s required to help teams thrive amid shifting power, purpose, and pace?

Who is this for?

This invitation is for senior decision-makers in AI-related leadership roles, including:

  • Chief AI Officers (CAIOs)

  • CTOs and Heads of ML/DS

  • Founders, funders, and system-level strategists

  • Policy, ethics, or innovation leads operating at scale

What AI Leaders Are Saying.

  • The question is no longer whether AI should be ehtical - it's whether businesses are willing to take responsibility for AI's impact.

    -Katie Harbath, Former Public Policy Director at Facebook and now Founder & CEO of Anchor Change

  • AI adoption isn’t just a technology challenge-it’s a leadership challenge. If leaders don’t champion AI at the highest level, it won’t scale.

    -Anna Litvak-Hinenzon, CAIO

  • Companies that fail to operationalize AI beyond pilot projects will fall behind. Scaling AI isn’t optional—it’s a business imperative.

    -Stefan Wendin, CTO

  • We may not have the same salary leverage as private firms, but we offer AI experts the chance to make a real difference in the world. For many, that’s the most compelling reason to stay.

    -Ann Dunkin, former CTO of DOE

  • Scaling AI isn’t just about more data and bigger models—it’s about creating an ecosystem where AI adoption is seamless across teams, functions, and leadership.

    - Marcus Nispel, CTO of Extreme Networks

Why Would I Join This Roundtable?

Because you’re not just scaling AI — you’re being asked to lead it.

And that requires more than strategic plans and technical execution. It demands a space to pause, reflect, and engage with peers who are navigating the same tensions — in real time.

This roundtable draws from a wide body of work — including insights from the CAIO Leadership Insights Report, ongoing conversations with dozens of senior leaders across AI, technology, and systems-level innovation, and the weekly curation behind the AI Leadership Compass Newsletter.

This round table offers:

A confidential, curated forum to step out of execution mode and gain perspective

In a world where AI is accelerating everything, this roundtable slows things down just enough to make better sense — and better decisions.

Space to test ideas, sense emerging patterns, and strengthen your own leadership clarity

Candid dialogue with other enterprise AI leaders facing the same systemic complexity

A focus not just on what to do, but who you need to be to lead AI responsibly and effectively

Insight into how others are wrestling with governance, talent, trust, and organizational readiness