In-Person

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

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

December 9, 2025

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

8:30am - 9:15am  Gartner Keynote

Unlocking AI — 5 Critical Insights Every CIO Needs Now

Joe Mariano headshot

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

Jeff Burlin headshot

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)

Paul Gentile headshot

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

Details coming soon.

9:40am - 10:25am  Executive Boardroom

Beyond Tech ― Evolving Organizations for AI Success

Paul Chapman headshot

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

Jason Trunk headshot

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

Kavitha Mariappan headshot

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

Jed Ayres headshot

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

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 headshot

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

12:30pm - 1:05pm  Keynote

Zero Trust & AI ― Strengthening Security, Reducing Complexity and Driving Innovation

Patrick Foxhoven headshot

Patrick Foxhoven

Chief Innovation Officer

Zscaler

Businesses stand to benefit from AI in unprecedented ways, but only if IT leaders overcome transformation challenges. This includes implementing a modern zero trust architecture to protect data and users, embracing AI while managing its risks and handling the technical and financial implications of ever-expanding environments. A risk-based approach to security ensures CIOs deliver a secure, phased transformation.


Join this session to:

  • Understand how zero trust and AI together, unlike firewalls, provide the strongest cyber defense by stopping threat actors from lateral movement within networks
  • Learn strategies for protecting AI applications developed in data centers and the cloud, while preventing data leaks from public AI applications
  • Discover how eliminating costly legacy hardware simplifies environments while cutting network and security costs

1:05pm - 1:30pm  Break

1:30pm - 2:15pm  Breakout Session

Mastering Vendor Contract Negotiations

Ann Madea headshot

Ann Madea

CIO & EVP

Simmons Bank

As strategic leaders, CIOs are tasked with negotiating contracts that not only meet technological needs but also drive business value. In this critical role, how are you leveraging your negotiation skills to secure favorable terms while maintaining strong vendor relationships and aligning with enterprise goals?


Join this session as Ann Madea, EVP & CIO, Simmons Bank shares tips on:

  • Balancing cost savings with quality assurance
  • Navigating complex vendor relationships
  • Aligning contract terms with strategic business objectives

1:30pm - 2:15pm  Breakout Session

Translating Cybersecurity ― Communicating Effectively with the Board

Rita Fisher headshot

Rita Fisher

CIO and EVP, Supply Chain

Reynolds Consumer Products

Boris Voltchenko headshot

Boris Voltchenko

CISO & VP IT Infrastructure

Reynolds Consumer Products

While board members are generally tuned into the importance of cyber governance, they don’t always understand the true risks of cybersecurity or their own role in its governance. It is the responsibility of the CIO & CISO to contextualize these risks in a way the board understands, and to continuously provide the right level of cyber education.


Join this CIO & CISO duo as they share boardroom strategies for:

  • Ensuring the board understands their role and responsibility
  • Leaving the technical acronyms at the door and focusing on business impact
  • Addressing the strategic opportunity that technology brings to organizations

1:30pm - 2:15pm  Executive Boardroom

Executive Boardroom

Rosie Rivel headshot

Rosie Rivel

CIO

Commerce

Details coming soon.

1:30pm - 2:15pm  Executive Boardroom

Observability Expectations for GenAI in Business-Critical Applications

Jacob Yackenovich headshot

Jacob Yackenovich

Program Director, Product Management - Instana

IBM

Generative AI is rapidly moving from experimentation to powering business-critical applications. For IT leaders, this shift raises a critical question — how do we ensure these new capabilities remain reliable, transparent and trustworthy in production at scale?

Join this session to discuss:

  • The evolving expectations for observability in the GenAI era
  • The challenges of monitoring AI-driven applications and ensuring they remain "up"
  • Critical visibility into AI behaviors to ensure business outcomes and customer engagement

1:30pm - 2:15pm  Executive Boardroom

Executive Boardroom

Details coming soon.

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

The AI Debate ― Championing AI’s Transformative Potential

Artificial intelligence has enormous potential to create tangible business value, but it’s going to take more than enthusiasm to get there.  How are you investing in data, change management and literacy to make AI a critical differentiator?


Join your peers for an interactive discussion on:

  • Identifying the most relevant value opportunities
  • Creating a strategy that fully and continuously aligns with the business
  • Setting realistic goals to build and mature an AI operating model

3:00pm - 3:45pm  Breakout Session

The AI Debate ― Do Current AI Solutions Really Live Up to the Hype?

Jon Morse headshot

Jon Morse

Vice President Information Technology

Bausch & Lomb Incorporated

While you likely have plans to increase your organization's artificial intelligence investments, you may believe the rhetoric surrounding the potential benefits of AI is inflating expectations. How can CIOs mitigate the negative aspects of AI hype and harness its power to create real value?


Join your peers for an interactive discussion on:

  • Defining and setting realistic goals for your organization
  • Managing the business’s expectations
  • Educating leadership on the complexity of AI adoption and governance

3:00pm - 3:45pm  Executive Boardroom

CIO Playbook ― Aligning IT Strategy with Business Outcomes

Kerry Brown headshot

Kerry Brown

Transformation Evangelist

Celonis

CIOs are no longer just technology leaders ― they are business leaders tasked with proving IT’s direct contribution to enterprise growth. Yet too often, IT investments struggle to show measurable outcomes. To succeed, CIOs must modernize their operating models, align IT priorities with business strategy and foster a culture of trust and accountability.


Join your peers to explore:

  • Practical ways to align IT strategy with enterprise priorities and outcomes
  • Approaches to modernize IT in a way that enables agility and resilience
  • Leadership strategies to elevate IT as a business value creator across the enterprise

3:00pm - 3:45pm  Executive Boardroom

What AI-Forward Companies Do Differently — Benchmarks for CIOs

Wade Foster headshot

Wade Foster

Co-founder & CEO

Zapier

How do you know that your AI is making a business impact? Success can’t be measured in a single tell-all metric but begins with a series of creative, practical KPIs that show real-world value and cost-savings. To really get value from your AI tools, it needs to be part of something bigger — something connected. AI orchestration is a key enabler for CIOs to deliver on their strategic objectives in a world where AI is increasingly central to business success.


Join this boardroom to discuss what leading companies have learned from executing millions of AI tasks by:

  • Tracking performance metrics that assess the real-world value and impact of AI tools and insights on business outcomes
  • Orchestrating end-to-end AI workflows that accelerate digital transformation and unlock new insights
  • Modernizing infrastructure to maximize ROI and respond quickly to market changes

3:45pm - 4:00pm  Networking Break

4:00pm - 4:35pm  Keynote

The AI Debate ― Potential vs. Hype

Corrado Azzarita headshot

Corrado Azzarita

Global CIO

The Kraft Heinz Company

After a day full of thought-provoking discussions, community members will take the stage to share their perspectives on the true value of artificial intelligence and its impact on the role of the CIO. Come ready to ask challenging questions and maybe even have your mind changed!


Pull up a chair alongside your peers to discuss:

  • Realistic expectations for AI business value
  • The impact AI will have on the workforce
  • The risk versus reward of AI investments

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 9, 2025

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.

Heather Bolick

Sr. Community Program Manager

heather.bolick@gartner.com