In-Person

Chicago CIO Community

Executive Summit

December 1, 2026 | Convene at 233 South Wacker Drive (Willis Tower)

December 1, 2026
Convene at 233 South Wacker Drive (Willis Tower)

Collaborate with your peers

Get together with Chicago's top CIOs to tackle shared business challenges and critical priorities facing your role today. Participate in this one-day, local program with peer-driven topics and interactive discussions with your true C-level peers.

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

Re-assessing Investment and Financial Impact of AI

Navigating Transformation, Culture, and Organizational Change

Collaboration across the C-Suite to Enable Technology Innovation and Efficiency

Chicago CIO Governing Body

The Governing Body Co-Chairs shape the summit agenda, ensuring that all content is driven By CIOs, For CIOs®.

Governing Body Co-Chairs

Rita Fisher

Reynolds Consumer Products
CIO & EVP, Supply Chain

Rajeev Khanna

Trucordia
CIO

Mike Parisi

ITW
VP & CIO

Jane Possell

CNA
EVP, Chief Information Officer, Analytics, Operations

Gagan Singh

Ascension
CIO

What to Expect

Interactive Sessions

Hear from CIO practitioners and thought leaders on how they're solving critical challenges impacting your role today in Keynote sessions, and join smaller, interactive discussions with your peers in Breakout and Boardroom sessions.

Community Networking

Make new connections and catch up with old friends in casual conversations during dedicated time for networking designed to better acquaint you with your Chicago CIO community.

Peer-to-Peer Meetings

Connect with like-minded peers in a private, one-on-one setting through Peer-to-Peer Meetings. You will be matched with peers in your community based on your shared interests and priorities.

Agenda

Breakout Sessions

Frontier AI Models — When Attack Speed Outpaces Operations

AI can now find and exploit a vulnerability in minutes — faster than any patch cycle or IT team can respond. For CIOs, this is a business risk, not just a security issue: the gap between attack speed and response speed can now disrupt operations. This is where autonomous remediation comes into play.
Join this session to learn:

  • Why the gap between attack speed and IT response is now a business risk
  • How automatic remediation cuts risk without more headcount or work
  • What this shift means for how you prioritize risk, budget and technology

Building Adaptive Teams—Managing Change and Opportunity

AI is reshaping IT, but true enterprise adoption takes more than new tools. Hear leadership perspectives on equipping teams at every level to confidently navigate and champion AI-driven transformation and discover practical strategies you can apply in your own organization. 

Join this session to explore:

  • Guiding IT teams through AI-powered change
  • Fostering a mindset of ongoing learning
  • Maintaining momentum for lasting talent development


When AI Moves Faster Than Trust — Control, Integrity, and Recovery

AI is scaling faster than organizations can control. As systems act autonomously across data and workflows, the real risk is loss of control, integrity, and recoverability. Establishing operational trust ensures systems are governed, impact is contained, and operations are restored when failure occurs.

Join this session to explore how to:

  • Maintain control as AI systems act autonomously
  • Ensure integrity of data and decisions under real-world conditions
  • Recover to a clean, trusted state when AI-driven systems fail


Gartner Keynote Session

Breaking the Leadership Patterns That Stall Transformation

Transformations rarely fail because of technology -- they fail when leaders allow competing priorities and dysfunctional behaviors to derail decision-making. If it feels like you've seen this movie before, it's because you have; these are the same patterns that have plagued transformations for decades. But as AI demands deeper collaboration across functions than any previous wave of innovation, unresolved leadership dynamics, organizational politics, and misaligned incentives become harder to ignore. The key to creating lasting change is recognizing and breaking these patterns before they become barriers to progress. That is what transforms a technology leader into an influential business leader.

Join this keynote to explore:

  • Building executive influence by creating alignment around outcomes, not activities
  • Navigating tradeoffs, competing priorities, and uncertainty with greater credibility and confidence
  • Moving beyond functional expertise to become a catalyst for business decisions


Executive Boardroom Sessions

From Wild Code to Governed Innovation

AI is enabling employees across the business to build apps, agents, and automation at an unprecedented speed. While this unlocks significant productivity and innovation, the result is a wave of, "wild code": AI-generated solutions developed outside traditional IT governance. As organizations struggle to balance speed with security and control, conventional approaches are proving insufficient. This session will explore how teams can build, run, and monitor AI-created work with governance embedded throughout.

Join this session to:

  • Understand the risks, cost, and overall business impact of "wild code"
  • Recognize why traditional governance models fall short in the AI era
  • Learn how to scale AI-driven innovation without sacrificing security or control

Rewriting the Build vs. Buy Playbook

 As AI transforms business operations and erodes longstanding biases, CIOs face renewed questions about how to balance building in-house solutions versus buying from vendors. What does today's decision framework look like as executives weigh multiple variables including speed, scalability, competitive advantage, and proprietary control?

Join this session to discuss:

  • Reassessing build vs. buy in the context of AI innovation
  • Weighing competitive advantage against cost, speed, and risk
  • Anticipating future orchestration models for hybrid technology strategies

Navigating the Cost and Dependency Trap of Innovation

As investment in AI accelerates, CIOs face mounting pressure to balance innovation with long-term cost and dependency risks. As organizations increasingly rely on a growing ecosystem of AI platforms, tools, and providers, the next wave of adoption could create new forms of vendor lock-in and escalating expenses, challenges that may prove even more complex than those encountered during the cloud era.

Join this boardroom to explore:

  • The hidden costs and commercial models shaping AI adoption
  • Risks of vendor lock-in and limited interoperability across AI platforms and solutions
  • Strategies to ensure informed decision-making and proactive management of future expenses



Keynote Session

The CIO Blueprint for AI Security

As attackers leverage AI to move faster than ever, traditional security strategies are falling behind. CIOs are now tasked with defending their organizations at machine speed, requiring a shift from reactive patching to proactive, autonomous protection. Leading enterprises are adopting continuous risk governance and measurable guardrails to ensure accountable AI adoption. CIOs are tasked with aligning business strategy with security outcomes and deliver board-level visibility into risk and remediation, all while enabling innovation.

Join this session to learn:

  • Aligning business strategy with real-time risk governance
  • Implementing measurable guardrails for accountable AI adoption
  • Delivering board-ready visibility into AI risk and remediation progress


We look forward to seeing you at an upcoming in-person gathering

Gartner cares about the health and safety of our community. If you are feeling unwell, please refrain from attending the conference. At this time, Gartner does not have any health-related requirements in place for attendance. Should this change, we will follow up with updated guidance.

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Key Sponsors

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Community Program Manager

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

Zander Petersen

Sr. Community Program Manager

971-499-8162

zander.petersen@gartner.com