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)

Join fellow CIOs for a day of peer connections, peer perspectives and Gartner insights

The Gartner Chicago CIO Community Executive Summit is the community’s signature event, bringing together CIOs for a full day of immersive, peer-driven discussions and curated networking. Connect with peers who share similar priorities, exchange real-world experiences and gain data-driven insights from Gartner analysts. Walk away with practical solutions, validated strategies and valuable connections, giving you greater confidence to lead through change.

Participate in discussions on 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 at an Executive Summit

Gain New Perspectives from Peers

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

Strengthen Your Peer Network

Catch up with familiar faces and build new relationships in your Chicago CIO Community through dedicated networking time in an intimate environment and curated, one-on-one conversations with peers matched based on shared priorities and interests.

Leverage Gartner Insights

Gain data-driven insights and field-tested best practices from a Gartner analyst in the opening Keynote, setting the context for peer conversations throughout the day on the most critical topics affecting your role.

Agenda

December 1, 2026

8:00am - 8:30am  Registration & Breakfast

8:30am - 9:15am  Gartner Keynote

Breaking the Leadership Patterns That Stall Transformation

Christiane Groth headshot

Christiane Groth

VP Analyst

Gartner

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

9:15am - 9:40am  Networking Break

9:40am - 10:25am  Breakout Session

Frontier AI Models — When Attack Speed Outpaces Operations

Jason Ellison headshot

Jason Ellison

VP, Product Management and Portfolio Lead

Tanium

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

9:40am - 10:25am  Breakout Session

Building Adaptive Teams—Managing Change and Opportunity

Gagan Singh headshot

Gagan Singh

CIO

Ascension

AI is reshaping IT, but true enterprise adoption takes more than new tools. Hear how Gagan Singh, SVP and CIO of Ascension, equips leaders and 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



9:40am - 10:25am  Executive Boardroom

Restoring Transparency and Trust in AI‑Driven Systems

Chris Conklin headshot

Chris Conklin

Field CTO

Dynatrace

As enterprises shift from human‑driven to human‑supervised operations, AI has introduced new forms of complexity that traditional monitoring can’t explain. The challenge is no longer whether systems are up, but whether leaders can clearly understand how decisions are made, where risk accumulates and why performance or cost changes in unexpected ways.

Join this session to discuss:

  • Where visibility breaks down in AI‑driven, hybrid and multi‑cloud environments
  • Why “nothing is down” no longer means systems are operating as intended
  • How CIOs re-establish transparency and trust as autonomous actions scale

9:40am - 10:25am  Executive Boardroom

From Wild Code to Governed Innovation

Colin Bentley headshot

Colin Bentley

Head of Product

Tines

Irene Oh headshot

Irene Oh

CIO

Network Services Company

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

10:25am - 11:10am  Networking Break

10:35am - 11:00am  Peer-to-Peer Meetings

Peer-to-Peer Meetings

Connect with like-minded peers in a 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.

11:10am - 11:55am  Breakout Session

Explore Evolving IT Strategy, Governance & Operative Models with Island

Michael Leland headshot

Michael Leland

VP, Field CTO

Island

Join this session to explore one of the community's top priorities this year: Evolving IT Strategy, Governance & Operative Models. Gain insights into key challenges, emerging approaches, and practical applications to help you navigate what's next.


11:10am - 11:55am  Breakout Session

Resilience on Trial — AI Cyber Simulation for CIOs

Bryan Willett headshot

Bryan Willett

CISO in Residence

Rubrik

Step into a realistic cyber crisis simulation where an AI-enabled attack disrupts critical business operations and enterprise technology services. Working through key decision points, you'll explore how executive leaders make the strategic calls that shape organizational resilience - balancing continuity, stakeholder trust, and recovery to return to a secure, trusted operating state after a major cyber event. CIOs will challenge assumptions about preparedness and what it really takes to recover.

Join this interactive session to learn more about:

  • AI-driven attacks and their impact on business continuity
  • Balancing risk, continuity, and recovery when systems, data, and AI are compromised
  • Leading cross-functionally through crisis, from decision-making authority to stakeholder communication

11:10am - 11:55am  Executive Boardroom

Rewriting the Build vs. Buy Playbook

Jeff Burlin headshot

Jeff Burlin

Senior Director, Executive Engagement Programs

Twilio

 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

11:10am - 11:55am  Executive Boardroom

Governance for Humans, Oversight for Agents

Enterprise governance was built for a human decision cycle: submit, approve, execute, close. AI agents don't work that way. As intelligent systems become embedded across workflows, CIOs must balance innovation, accountability and operational control without slowing the business.

In this boardroom, we’ll discuss:

  • Evolving governance models for AI that operate continuously across workflows and decisions
  • Creating visibility, accountability and trust without introducing new layers of bureaucracy
  • Moving from task automation to outcome orchestration across teams and functions


11:55am - 12:30pm  Lunch Service

12:30pm - 1:05pm  Keynote

The CIO Blueprint for AI Security

Sanjit Ganguli headshot

Sanjit Ganguli

CTO in Residence

Zscaler

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

1:05pm - 1:30pm  Break

1:30pm - 2:15pm  Breakout Session

The Coordination Imperative — Connecting IT Decisions to Business Outcomes

CIOs are under pressure to turn AI investments into business value while strengthening resilience, improving productivity, and controlling costs. As AI becomes embedded across the enterprise, it is compounding existing complexity and silos, making it harder for teams to understand impact, decide what matters most, and act with confidence. Limited resources and growing demands require greater alignment, clear ownership, and a more coordinated approach to decision-making and execution.
Join this session to explore how CIOs can:

  • Build an operating model that connects operational insight to business priorities and timely action
  • Create a framework for shared context across teams, strengthening accountability and governing AI-driven automation
  • Focus resources on their highest priorities, reduce disruption, and give teams more capacity to innovate

1:30pm - 2:15pm  Executive Boardroom

The Redesign Challenge of AI Transformation

Nathan Rawlins headshot

Nathan Rawlins

CMO

Lucid Software

Andy Bhojwani headshot

Andy Bhojwani

CIO

Nidec

Most enterprise AI is being bolted onto processes designed for a pre-AI world. If your AI roadmap feels stuck, you’re not alone—most organizations are redesigning with blind spots. What if the real barrier isn’t technology, but hidden processes and decisions?

Join this boardroom to discuss:

  • Moving AI from individual adoption to institutional transformation
  • Surfacing the processes, systems, and decision logic that make redesign possible
  • Sequencing visibility, redesign, and AI deployment so each phase compounds the next

1:30pm - 2:15pm  Gartner Boardroom

AI Economics — Closing the Gap Between Cost and Value

Janice Wurz headshot

Janice Wurz

Executive Partner

Gartner

Unlike traditional IT investments, AI introduces highly variable, usage-driven costs that challenge conventional budgeting and governance approaches. How are CIOs adapting to connect cost, value and accountability across the enterprise while enabling AI adoption at scale?

Join this session to discuss:

  • Measuring your AI token spend: Ensuring tokens are best spent where you’ll find the most value
  • Connecting AI initiatives to real-world results: Finding your most valuable use cases and business outcomes
  • Sharing the responsibility for AI across the enterprise: Success relies on IT and your stakeholder’s leadership

2:15pm - 3:00pm  Networking Break

2:25pm - 2:50pm  Peer-to-Peer Meetings

Peer-to-Peer Meetings

Connect with like-minded peers in a 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.

3:00pm - 3:45pm  Breakout Session

Making the Call on Risk

Soumit Nandi headshot

Soumit Nandi

Global CTO

Live Nation Entertainment

Jane Possell headshot

Jane Possell

EVP, Chief Information Officer, Analytics, Operations

CNA

Every major AI decision raises a difficult question: move ahead and manage risks as they emerge, or pause until stronger safeguards are in place? Soumit Nandi and Jane Possell share contrasting approaches to these decisions and discuss how CIOs can engage the board as risks evolve. 

Join this peer chat to explore: 

  • Balancing urgency, experimentation, and practical safeguards 
  • Defining ownership for AI risk across the enterprise 
  • Staying aligned with the board as risks emerge and oversight requirements evolve 

3:00pm - 3:45pm  Executive Boardroom

Cyber Risk as Enterprise Risk

As the enterprise faces a growing range of business risks, cybersecurity can no longer be managed in isolation. Strategic CIOs must seamlessly embed cybersecurity into enterprise risk frameworks to improve visibility, strengthen resilience and inform business decisions.

Join this session to discuss:

  • Integrating cyber risk into enterprise risk management and governance
  • Measuring cybersecurity through business impact and resilience outcomes
  • Aligning IT, security and business leaders around shared risk priorities


3:00pm - 3:45pm  Executive Boardroom

Discuss Realizing Enterprise Value from AI with Your Peers

Join this interactive discussion with fellow CIOs on Realizing Enterprise Value from AI to exchange perspectives, explore common challenges, and uncover practical ideas and strategies you can apply within your organization.

3:45pm - 4:00pm  Networking Break

4:00pm - 4:35pm  Keynote

Business Transformation That Delivers

Anuj Gaur headshot

Anuj Gaur

VP, Global IT

The Marmon Group

Drawing on major, multiyear transformations, this session explores the leadership lessons, guardrails, and CIO practices that turn significant investments into lasting business outcomes—including how to stay engaged at the right level once execution begins.

4:35pm - 4:45pm  Closing Comments and Prize Drawing

4:45pm - 6:00pm  Governing Body Reception

Governing Body Reception

Finish the day sharing lessons learned with your peers over light fare and drinks at this closing reception hosted by your governing body members.

December 1, 2026

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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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