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
Agenda
8:00am - 8:30am Registration & Breakfast
8:30am - 9:15am Gartner Keynote
Breaking the Leadership Patterns That Stall Transformation
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
Hosted by Tanium
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
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
Hosted by Dynatrace
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
Hosted by Tines
Colin Bentley
Head of Product
Tines
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
Hosted by Island
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
When AI Moves Faster Than Trust — Control, Integrity, and Recovery
Hosted by Rubrik
Jason Cook
Field CTO Americas
Rubrik
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
11:10am - 11:55am Executive Boardroom
Rewriting the Build vs. Buy Playbook
Hosted by Twilio
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
Hosted by Smartsheet
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
Apply to Participate
Each application is carefully vetted to ensure members meet established criteria, preserving the quality of the network and enabling meaningful, peer‑level discussions among leaders from the world’s leading organizations.
Once you submit your application, a Community Program Manager will schedule a conversation to understand your priorities and interests and complete onboarding, including access to year‑round community events.
Location
Venue & Accommodation
Convene at 233 South Wacker Drive (Willis Tower)Parking & Transportation
Nearby Parking Information:
One Parking 227 W Monroe St
Public Parking 111 S Wacker Drive
183 Monroe Garage 183 W Monroe St
230 S LaSalle St
211 W Adams St
217 S Wells St
Nearby Subway Station:
QuincyStation: Brown, Red, Pink, Purple Lines
Chicago CIO CISO Executive Summit Nearby Hotels
Canopy By Hilton Chicago Central Loop
226 West Jackson Blvd
Chicago, IL 60606
Distance from venue - 0.1 mile
151 W Adams St
Chicago, IL 60603
Distance from venue - 0.2 mile
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
172 W Adams St
Chicago, IL 60603
Distance from venue - 0.2 miles
Community Program Manager
For inquiries related to this community, please reach out to your dedicated contact.
