2026 Chicago CIO Community Inner Circle

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Collaborate with your peers

Join Chicago's top CIOs for an intimate networking dinner and facilitated discussion on key business challenges. Enjoy a relaxed evening of dinner and drinks with your peers to share best practices, make new connections and build professional relationships.

Join your peers to discuss the most critical issues impacting CIOs today:

Enabling innovation and productivity through human-AI collaboration

Adapting vendor strategies to meet changing enterprise demands

Empowering organizational transformation with effective change leadership

Governing Body Co-Chairs

Agenda

September 1, 2026

4:30pm - 5:30pm Executive Networking Reception

5:30pm - 6:30pm Discussion Topics

Navigating the New Era of Collaboration and Change

Jeff Burlin

Senior Director, Executive Engagement Programs

Twilio

As AI agents and digital copilots become part of daily work, CIOs face a pivotal challenge: building a culture where humans and AI not only coexist but collaborate to drive innovation and productivity. This shift requires more than technical integration—it calls for reimagining roles, workflows, and executive expectations.

CIOs must balance the promise of AI-augmented work with the realities of change management, ensuring employees feel empowered, not displaced, and that agent interfaces are intuitive and secure. At the same time, leaders must navigate evolving vendor ecosystems, budget constraints, and the ongoing buy vs. build debate.

Discussion Questions:

What initial focus area creates the strongest foundation for scaling?
How are you supporting teams in human-AI collaboration?
How do you balance usability and security in agent interfaces?
How are executive expectations changing with AI?
How do you approach vendor risk and buy vs. build decisions?
What change management strategies have worked best for you?
What lessons from recent AI projects guide your next steps?

6:30pm - 7:00pm Networking Break

7:00pm - 8:00pm Summary Discussion & Dinner

8:00pm - 9:00pm Social Hour

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Gartner facilitates exclusive, C-level communities by personally qualifying and understanding the priorities, challenges and interests of each member.

Our selective approach maintains the high quality of the network and ensures top-level discussions with peers from the world’s leading organizations.

Each application will be reviewed, and once your participation is confirmed, you will have access to year-round community programs.

Community Member Criteria

To ensure peer connections and conversations at the highest level, members must meet the following criteria:

- C-level or senior most executive for respective function

- Organization revenue of $500M+

Exceptions are considered.

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Location

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The Metropolitan

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For inquiries related to this community, please reach out to your dedicated contact.

Zander Petersen

Community Program Manager

971-499-8162

zander.petersen@gartner.com