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May 22 2026

CXO Connect.

Directors

Date
Fri · May 22 2026
Time
10:00 – 11:30 PT1:00 – 2:30 ET
Format
Virtual roundtable

AI is already moving. Now leaders need to compare what happens after.

Who
Directors leading transformation across their org and the SDLC.
Conversations
Small group, peer-only, camera-on conversations.
Rules
Conversations are off the record and should stay that way.
Format
Moderated open discussion. If you join, you are expected to share your personal experiences as a leader.

Every executive is adopting AI.

The interesting conversations are no longer about whether to start. They're about what happens after.

What breaks. What scales. What creates value. What creates risk. What leadership teams wish they had known before they rolled AI into customer experiences, internal operations, and core business processes.

CXO Connect is a private roundtable for senior leaders who have lived through those decisions. Leaders who have shipped, broken, fixed, and re-shipped AI in organizations where outcomes matter.

Why virtual, why now

The challenges leaders face with AI are remarkably similar, regardless of industry or geography. The opportunity is learning from people outside your own market, company, or network.

A virtual format allows us to bring together senior leaders from across cities, states, and countries into a single conversation. Perspectives that would rarely intersect in a traditional local event can share lessons learned, compare approaches, and discuss what's actually working inside their organizations.

Our goal is to build a community that transcends geography, connecting leaders who can learn from one another's successes, mistakes, and hard-earned experience.

The Directors room opened.

The inaugural CxO Connect for the Directors cohort. Twelve operating leaders, no slides, and ninety minutes of candid conversation about shipping AI inside real organizations.

This session has concluded. The conversation continues through the rest of the 2026 series.

The conversation is part of the record.

This session ran under Chatham House rule. Notes from the room inform the next session in the series.

Prefer to write directly?cxoconnect@thisdot.co

Registration closed.

This session has passed. View the upcoming sessions to register for the next one in the series.