
Chicago CIO Community
Executive Summit
December 9, 2025 | Convene at 233 South Wacker Drive (Willis/Sears Tower)
December 9, 2025
Convene at 233 South Wacker Drive (Willis/Sears 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:
Defining and Delivering Value Amidst Rapid Technology Innovation
Building and Maintaining a Resilient Cybersecurity Strategy
Leading the Enterprise Through Disruption and Uncertainty
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 and EVP, Supply Chain

Ron Guerrier
Save the Children
CTO

Rajeev Khanna
Trucordia
CIO

Laura Kohl
Morningstar
CIO

Mike Parisi
ITW
VP CIO

Jane Possell
CNA
EVP, Chief Information Officer, Analytics, Operations

Gagan Singh
Ascension
Chief Information Officer

Tom South
Northern Trust
CIO
What to Expect
Agenda
8:00am - 8:30am Registration & Breakfast
8:30am - 9:15am Gartner Keynote
Unlocking AI — 5 Critical Insights Every CIO Needs Now

Joe Mariano
Senior Director Analyst
Gartner
Though it is a top priority for CIOs, Gartner research shows only a small fraction of employees use AI effectively at work. Senior Analyst Joe Mariano breaks down five critical data-driven insights that, when addressed, can fast-track your organization’s AI adoption. He will then showcase five compelling real-world case studies, each paired with targeted, actionable strategies designed to drive enterprise-wide AI transformation.
Join this session to gain strategies on:
- Accelerating AI adoption
- Empowering your leadership team
- Delivering measurable business impact
9:15am - 9:40am Networking Break
9:40am - 10:25am Breakout Session
Lessons From the First Inning of AI
Hosted by Twilio

Jeff Burlin
Senior Director, Executive Engagement Programs
Twilio
Recent studies on GenAI initiatives reveal that many projects intended to drive rapid revenue growth fell flat due to flawed enterprise integration, misalignment in resource allocation, and a fundamental learning gap for both tools and organizations. What are the lessons learned from AI’s successes and failures that CIOs can apply to their own initiatives to increase the odds of success?
Join this session to examine:
- Assessing use cases for real value without falling prey to “AI FOMO”
- Designing flexible core architectures to experiment and scale AI projects quickly
- Balancing risk and trust in digital initiatives
9:40am - 10:25am Breakout Session
Driving Digital Innovation and Enterprise Productivity Through Digital Employee Experience (DEX)
Hosted by Nexthink

Paul Gentile
Senior Vice President, Strategic Marketing
Nexthink
Enterprise productivity is top of mind for business leaders everywhere and CIOs play a crucial role in showcasing progress and true value to the business in this mission. A well-crafted digital employee experience (DEX) strategy that addresses changes in the way employees work and interact with digital tools will ensure that your processes and technologies advance the mission of a high performing workforce and improved enterprise productivity.
Join this case study to discuss a journey with DEX, including:
- Improving operational efficiency and business outcomes
- Measuring IT impact to strategic business growth
- Leveraging DEX to improve optimization and visibility of IT assets
9:40am - 10:25am Executive Boardroom
Executive Boardroom
Hosted by Tata Consultancy Services
Details coming soon.
9:40am - 10:25am Executive Boardroom
Beyond Tech ― Evolving Organizations for AI Success
Hosted by Cisco

Paul Chapman
Vice President Business Strategy
Cisco Systems
You can’t unlock AI’s full value without rethinking your people strategy. The gap is widening between those riding the AI wave and those struggling to stay afloat. We’re pouring investment into platforms, models and copilots, but what about our people? Without inclusive upskilling, AI won’t feel like empowerment; it will feel like exclusion.
Join this boardroom to discuss:
- The fundamental architectural necessities that AI is driving in technology and operations
- Aligning workforce AI proficiency as a core pillar of AI ROI
- Evolving talent strategy, org design and change management in parallel with AI investments
- Building cross-functional partnerships to drive AI adoption and success
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
Reducing Application Delivery Tech Debt from the Inside Out
Hosted by Island

Jason Trunk
Chief Enterprise Architect
Island
With high volumes of sensitive data now flowing through web browsers, three in five organizations say data leakage is likely given current IT and security infrastructures. Stop playing catch-up. Discover new approaches to enterprise operations to reduce risk while simplifying operations.
Join this session to discover:
- How disparate IT and security solutions create technical debt
- What challenges impact internal and end user stakeholders
- How simplifying IT can strengthen security, and boost productivity
11:10am - 11:55am Breakout Session
A Resilient Path Through Emerging Agentic AI Risks
Hosted by Rubrik

Kavitha Mariappan
Chief Transformation Officer
Rubrik
By 2028, Gartner predicts that 15% of daily business decisions will be made autonomously by AI agents — creating new risk surfaces with direct operational impact. CIOs must extend resilience practices to agentic AI by quantifying agent risk, capturing and monitoring agent activity and preparing recovery playbooks that reverse unauthorized or harmful agent actions. This holistic approach ensures workflows remain intact, data integrity is preserved and business continuity is upheld — even when AI agents misstep.
Join this session to learn:
- How to set resilience standards for AI agents to align with enterprise risk
- Proven strategies for detecting and containing rogue or unintended AI behavior
- Playbooks for rapid rollback and business continuity when AI disrupts workflows
11:10am - 11:55am Executive Boardroom
Achieving a Workplace that Runs Itself ― A Digital Employee Experience (DEX) Conversation
Hosted by Control Up

Jed Ayres
CEO
Control Up
As hybrid work evolves and AI transforms workflows, the need for seamless, intelligent and proactive digital experiences is more critical than ever. How are today’s technology leaders investing in DEX in a way that improves workplace productivity and drives business outcomes?
Join your peers to discuss:
- Advancing through the digital workplace maturity model
- Harnessing AI to optimize digital workflows
- Building a resilient, future-ready IT foundation
11:10am - 11:55am Executive Boardroom
The Intelligent Enterprise — The Fusion of Analytics, Automation and AI
Hosted by Alteryx
The convergence of AI, analytics, and intelligent automation is creating a new era of autonomous business processes. CIOs can move beyond fragmented systems to provide rapid insights, optimized decision-making, and unprecedented efficiency across the enterprise. Governing AI and analytic processes while enabling the business accelerates AI adoption and innovation
Join this session to discuss:
- Principles for governing and operationalizing the intelligent enterprise
- Steps to uplevel and create a technology and AI forward workforce
- Lessons for leaders for creating a culture of AI and analytics
11:10am - 11:55am Executive Boardroom
Building Strong Data Foundations

Julie Slezak
Executive Partner Data and Analytics – Americas Public Sector
Gartner
AI is coming from everywhere — and so is data. CIOs must have a strategic approach to AI-ready data as it is one of the most important ingredients of AI and GenAI success. Whether you are at the beginning of your journey or ready to implement Agentic AI, you will need to prepare and maintain your data.
Join this session to:
- Discuss what is important for AI-ready data
- Right size your ambition for AI based on your current modernization efforts
- Share your innovative approaches and learn from your peers
11:55am - 12:30pm Lunch Service
Apply to Participate
Apply to participate in the Chicago CIO Community Executive Summit.
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.
Location
Venue & Accommodation
Convene at 233 South Wacker Drive (Willis/Sears Tower)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
Hilton Garden Inn Chicago Central Loop
245 S Franklin St.
Chicago, IL 60606
Distance from venue - 0.2 mile
The LaSalle Chicago, Autograph Collection
208 S LaSalle St
Chicago, IL 60604
Distance from venue - 0.4
Community Program Manager
For inquiries related to this community, please reach out to your dedicated contact.