

The AI Leadership Dialogue - Chicago 2026
Executive Dialogues on AI
A private convening of executives, investors, and enterprise leaders
We are pleased to convene the inaugural Executive Dialogues on AI - the first in a series of intimate, invitation-only conversations bringing together a select group of senior executives and institutional investors navigating the opportunities and decisions emerging around AI.
The premise is simple: some of the most valuable insight comes from those actively doing the work. This gathering is designed to create a candid, peer-level exchange around what is working well with AI adoption, what has proven more difficult than expected, where organizations are seeing meaningful value today, and where the next AI opportunities may lie.
There will be no panels or formal presentations. Instead, the conversation will be shaped by small group of leaders around the table: their experiences, questions, lessons, and perspectives. Together, we will explore how organizations are moving from experimentation to meaningful adoption, where AI is beginning to reshape businesses and portfolios, and what leaders are considering as they look ahead.
The format is intentionally limited to small group of participants to allow for a substantive and open exchange. Our aim is not to arrive at a single point of view, but to create a trusted setting where leaders can compare approaches, challenge assumptions, and leave with perspectives they may not encounter within their own organizations.
By invitation · Limited seating
Convened by Performance AI