Chief Context Series

The Second Act of Enterprise AI

Context. Connected. Governed. Actioned.

Bringing together CIOs, Chief AI Officers, CDOs and Data/AI leaders across North America. This series: what it takes to move past the pilot and into governed, adopted, enterprise-wide deployment.

Request an invitation See the cities

Cities

NAMER city list TBC

Format

Executive Roundtable SeriesClosed-door, 15 to 20 senior leaders per city

Ground rules

Peer-ledChatham House rules

Overview

The gap is not a model problem. It is a context problem.

Most enterprises have run the AI pilot. Fewer have made it stick. The gap between a working proof of concept and a governed, adopted, enterprise-wide deployment is where most AI initiatives stall, and it is rarely a model problem. It is a context problem: information scattered across tools, permissions that do not hold up at scale, and no clear way to measure whether any of it is actually working.

The Chief Context Series is a standing roundtable community for the executives who own that problem, wherever it shows up on their title. This session, The Second Act of Enterprise AI, brings together data and technology leaders across financial services, government, retail, healthcare, telecommunications, energy and utilities, and higher education, working through what scaled AI adoption actually looks like inside a real organization.

Talking points

What the table works through.

Why context, not the model, is now the real infrastructure decision

Permissions and governance as an extension of context, not a separate checkbox

Where context gaps quietly drive up AI cost and token waste

Who actually owns context inside the business, and why that is now a board-level question

The series

One community, six markets, one connected conversation.

Glean maps how everything at work relates through the Enterprise Graph. The series is built the same way: each city is a node, every table adds context, and what the community learns compounds across the region.