Curated Agenda
Every session is scoped around a single, high-stakes question, shaped from pre-reads submitted by the attending leaders themselves. No panels, no pitches, no performative keynotes.
Private Roundtables
Where influence meets intelligence.
An invitation-only series of virtual roundtables for senior leaders navigating the hardest questions of enterprise transformation (AI implementation, operating model redesign, and the impact of change) without the theatre of a conference floor.
The Experience
A modern maecenas circle. Held in digital.
The historical maecenas convened the sharpest minds of a generation under a single roof (patrons, builders, and dissenters) so that influence could refine itself against intelligence. Our roundtables take that idea and translate it for the enterprise era.
Small enough to be candid. Curated enough to be useful. Quiet enough that the room feels like a private study rather than a broadcast.
A Safe Space for PeersSmall. Candid.
The Protocol
Engineered for digital insight.
Discreet by Design
A safe space to discuss real challenges amongst peers. Small by design. What is said in the room stays in the room, so the conversation can actually be useful instead of polished for the transcript.
Expert Allies
Each roundtable is anchored by practitioners who have already done the work. You leave with named contacts, operator-grade frameworks, and the confidence of having seen the terrain.
Inaugural Series
The AI implementation reality.
Our opening series convenes CIOs, CTOs, and transformation leaders around the question nobody wants to ask in public: what does AI readiness actually require from the operating model, and where are the fault lines hiding?
No vendor demos. No analyst slides. Just a curated table of practitioners trading what worked, what failed, and what they'd do differently, held by a moderator who has installed the governance on both sides of the table.
The conversations most leaders need are the ones that can only happen with their peers, off the record, with someone who knows how to hold the room.
Jessica Caresse White, Host, J.Caresse & Company
Host & ModeratorJessica Caresse White
Invitation Only
Seats are deliberately few.
Twelve seats per session, to keep the conversation candid and the room generous. Tell us who you are to get your passcode, choose a session, and reserve your seat. If you already have a code from an invitation, use it directly.
Next session
2 PM Eastern
2026
2027
Always a Monday, 2 PM Eastern, over Zoom. Choose a date to reserve it.
Past Sessions
What the room found.
Every session becomes a white paper: the anonymized themes, set against the research. This is the roundtable's running record on AI readiness and AI behavioral change, written for organizations that are intentional about changing how their people look at work: moving employees from task thinking to systems thinking and systems orchestration, so AI lands on a process that can hold it.
AI Education Before AI Implementation: Why the Human Layer Comes First
Operators in this session found that AI readiness fails before the technology arrives: organizations select tools before they can state the problem, assign adoption to technology teams who do not own the outcome, and manage employee fear of displacement through silence rather than transparency. The group developed a working distinction between decisions that can move at the speed of individual experimentation and decisions that require deliberate pacing at the program and governance level. The white paper details the behavioral telemetry infrastructure and business-ownership model the room converged on.
- Defining AI Education Before Deploying AI Tools
- People-First Frameworks Versus Technology-First Deployment
- Fear, Transparency, and the Job Displacement Conversation
AI Governance in Practice: Ownership, Agentic Risk, and the Gap Between Policy and Reality
Senior operators in this session found that AI governance is being stood up reactively, with no single function holding the authority or technical depth to own it across HR, IT, legal, and business. The sharpest pressure point was the move to agentic AI: employee-built agents and MCP connectors are outpacing the identity and access controls organizations have in place, while shadow AI use and workforce reductions have left change management too thin to close the gap. The white paper details what the room concluded about governance structure, agent risk, and where to start when the foundation is still being built.
- Defining and Owning AI Governance
- Shadow AI and the Limits of Lockdown
- Agentic AI and Identity-Based Access Control