CIO 100 Leadership Live Chicago: Event Agenda & Key Sessions

Get ready for a full day of actionable insights, expert sessions with IT leadership, and valuable networking opportunities focused on enterprise innovation with enterprise technology innovators. The full agenda for CIO 100 Leadership Live is in process and more updates coming soon!

Tuesday, October 13

8:30 - 9:45 am
Executive Roundtables

Join an interactive discussion on the opportunities and challenges of implementing AI and next-generation technologies across the enterprise. Attendees will exchange strategies, lessons learned, and priorities for leading successful transformation.

9:00 - 9:45 am
Breakfast and First Connections

Grab breakfast and coffee, find a seat, and meet the people you’ll be learning alongside all day.

9:45 - 10:00 am
Real Talk: Stories from the Leadership Live Series

Hear from CIOs who’ve been in the chair, the decisions that defined them, the projects that nearly broke them, and the lessons they wish someone had handed them earlier. Curated excerpts from the CIO Leadership Live interview series, selected because they’re honest and insightful.

Includes interviews with: Annie Baymiller, EVP & Global CIO, Owens Corning; Chris Nardecchia, CIDO, Rockwell Automation; Sastry Durvasula, Chief Operating, Information & Digital Officer, TIAA; Bob McCowan, Former CIO, Regeneron Pharmaceuticals and Deborah Youmans, VP & CIO, MITRE

10:00 - 10:05 am
Welcome and Introduction
10:05 - 10:40 am
Real Leaders, Real Challenges: Championing Tech-Enabled Business Transformation

Today’s bold CIOs are rewriting the rules of business transformation, and they’re doing it in real time, under real pressure, with real stakes. Join us to hear from a select group of courageously innovative technology leaders who will share the successes that are moving their organizations forward, along with the learn-from-failure moments that are reshaping their playbooks. These leaders help stakeholders rethink everything, from culture and talent, to how we work and architect the future of the business, to leveraging new operating models and technology strategically. No theory. No platitudes. No pretenders. Just practitioners speaking to practitioners, with candor, humility, and practical wisdom you can use to lead your team and company through transformation in the age of AI.

10:40 - 11:00 am
Partner Session

In this dynamic sponsor‑led session, leading solution providers explore how today’s innovations are driving impact across the enterprise. Expect bold thinking, practical takeaways, and new approaches designed for CIOs tackling complex challenges.

11:00 - 11:30 am
Networking Break: Conversations That Spark Connections

Coffee, vendor conversations, and the hallway discussions that can be just as engaging as the sessions. Take the time. These unplanned moments often become the ones you remember most.

12:05 - 12:25 am
Partner Session

In this dynamic sponsor‑led session, leading solution providers explore how today’s innovations are driving impact across the enterprise. Expect bold thinking, practical takeaways, and new approaches designed for CIOs tackling complex challenges.

12:25 - 12:55 pm
Hot Topic Discussion Groups

Join a conversation of your choice to listen, learn and share experiences around the table.

12:55 - 1:55 pm
Networking Lunch

Enjoy lunch with fellow leaders, and connect with our sponsors to explore solutions that can support your most pressing challenges.

Next CIO Luncheon

The next generation of leaders are invited to this curated career development and networking luncheon designed specifically for high-potential technology leaders who are not yet in the C-suite, but well on their way.

Pre-registration required.

1:55 - 2:30 pm
Securing Trust in the Agentic Economy

AI agent adoption has moved from experimentation to productization at scale, which introduces both innovation and risks stemming from AI. This session examines the threats at play and how CISOs can unlock business growth while securing their organizations at machine speed and ultimately maintain trust with customers. Learn how organizations are balancing speed, innovation, and security in high stakes environments. Come with questions.

2:30 - 3:05 pm
AI: From Experimentation to Enterprise Impact

Many organizations have moved beyond pilots, but few have achieved scaled impact. This session goes inside real enterprise AI deployments, unpacking what worked, what failed, and what it actually takes to operationalize AI across the business. Expect honest lessons on governance, cost, talent, and how to move from hype to measurable outcomes. Come with questions!

3:05 - 3:35 pm
Innovation Showcase

After winning a CIO 100 Award, what came next? Find out how past CIO 100 award-winning companies have iterated their projects since being recognized as digital innovators. In this self-directed experience, you can visit presentations that match your interests, ask questions about technical and leadership challenges, and network with small groups of peers. Presentations will repeat, so you have the chance to check out as many as you like.

3:40 - 4:10 pm
Think Like a VC: Investment Shifts Towards Focused AI Applications

Top investors share where they are placing bets, which technologies are overhyped, and what signals CIOs should pay attention to. This session helps technology leaders separate real innovation from noise and align their roadmaps with where the market is heading. Come with questions!

4:10 - 4:45 pm
What’s Next for the CIO: Preparing for the Next 12–24 Months

The pace of change is accelerating. In this closing conversation, CIOs reflect on what’s coming next, from AI economics to organizational redesign. Attendees will leave with a clear sense of priorities and the decisions that will define success in the near future. Come with questions!

4:45 - 5:45 pm
Networking Reception
The day’s conversations don’t have to end here. Drinks, connections, and chat with attendees and speakers.