In-Person

Chicago CIO Community

Executive Summit

May 12, 2026 | Convene at 233 South Wacker Drive (Willis Tower)

May 12, 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:

Driving Business Outcomes Through Agentic AI and Board Alignment

Navigating Ecosystem Modernization and Aggressive Rationalization

Optimizing Technology Investments for Strategic Agility and Resilience

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

May 12, 2026

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

8:30am - 9:15am  Gartner Keynote

Gartner Analyst Keynote

Join us for an exclusive keynote from a leading Gartner Analyst, offering forward-looking insights and strategies on emerging trends shaping the future of technology and business.

9:15am - 9:40am  Networking Break

9:40am - 10:25am  Breakout Session

Rewired for Results — Integrating Care, Culture, and Technology

Nathan Frank headshot

Nathan Frank

SVP & Chief Digital and Technology Officer

Aetna

When Nathan Frank stepped into his role at Aetna, a CVS Health Company, the organization faced real challenges in digital engagement and operational performance. By focusing on innovation, cultural change, and a business-oriented approach, Frank and his team charted a new course for user experience and business recovery. Today, Aetna is recognized as a leader in digital healthcare, with lessons that extend well beyond the industry.

Join this session as Frank discusses:

  • Advancing digital member experience to outperform industry benchmarks
  • Fostering a culture of innovation and accountable product teams
  • Streamlining multiple digital touchpoints into a cohesive member journey

9:40am - 10:25am  Breakout Session

Breakout Session by Cloudflare

Further details will be shared soon.

9:40am - 10:25am  Executive Boardroom

From Experimentation to Proven Value — Scaling the Agentic Enterprise

Despite strong AI investment, many organizations are trapped in a cycle of experimentation. To reach production, CIOs must overcome fragmented data silos, skyrocketing development costs, and the “black box” of AI governance. How can CIOs bridge the gap between prototypes and experimentation to enterprise-grade execution and business outcomes?

Join this session to discuss:

  • Accelerating deployment by integrating AI into core workflows and bypassing traditional development bottlenecks
  • Weaving AI agents and agentic workflows into end-to-end processes for optimal human-AI collaboration
  • Establishing governance and compliance frameworks that ensure your AI strategy is secure, compliant, and built for long-term ROI

9:40am - 10:25am  Executive Boardroom

Redefining Workflows - Unlocking Automation and Agility

Joe Murphy headshot

Joe Murphy

VP, Data & AI Technology

Acceldata

As organizations accelerate analytics and AI adoption, reliable data and automated workflows are essential for agility and risk control. Leading teams are moving beyond reactive monitoring to achieve proactive, end-to-end visibility and embed governance-driven automation.

Join this session to:

  • Build trusted, scalable data workflows
  • Achieve visibility across modern data ecosystems
  • Embed automation for secure, decision-ready operations

9:40am - 10:25am  Executive Boardroom

Securing the Rise of AI Identities

According to the International Data Corporation, the number of AI identities is expected to reach 1.3 billion in just two years. Yet many organizations don’t secure AI identities effectively, granting excessive access and relying on outdated, slow processes.

Join this session to learn how to:

  • Identify gaps in agent access visibility, ownership, and governance
  • Address the unique challenges of identity security in AI environments
  • Build scalable identity foundations to enable innovation and efficiency

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

Activating Unstructured Data and Agents in the Enterprise

The shift from basic AI assistants to autonomous agents is reshaping the enterprise, turning passive tools into scalable workflows. Real advantage emerges when intelligence is grounded in an organization’s unique, proprietary content. As leaders move beyond early experiments, the priority becomes breaking down silos and establishing governance that ensures agents operate on a reliable foundation.

Join this interactive session to learn how to:

  • Prioritize measurable growth beyond LLM hype
  • Connect content to unlock meaningful AI performance
  • Understand the monetary and labor opportunity costs of AI transformation

11:10am - 11:55am  Breakout Session

From Fragmentation to Flow — The CIO’s Next Move

Despite advances in AI and workflow automation, many enterprises still struggle to turn strategic vision into real-world results. Persistent silos, integration headaches, and evolving security demands continue to challenge even the most forward-thinking CIOs. Yet, as agentic architectures mature, new opportunities emerge to move from incremental improvements to true organizational flow.

Join this session to explore:

  • Building a roadmap for unified agentic ecosystems
  • Measuring and scaling business impact beyond pilots
  • Fostering a culture that embraces continuous, AI-driven change

11:10am - 11:55am  Executive Boardroom

Traditional ERP is Dead — What's Next?

Rod Masney headshot

Rod Masney

Regional CTO, North America

Rimini Street

Agentic AI is transforming work and prompting leaders to rethink traditional suites and modernization strategies. This boardroom will examine how agentic AI is unbundling ERP responsibilities, reshaping process orchestration and enabling smarter service layers.

Join fellow CIOs to explore:

  • The rise of service layers, workflow engines and AI agents
  • What’s replacing monolithic ERP models
  • Key assumptions to challenge when evaluating vendor roadmaps

11:10am - 11:55am  Executive Boardroom

Executive Boardroom by Palo Alto Networks

Further details will be shared soon.

11:10am - 11:55am  Gartner Boardroom

The Great Blur — How Agentic Coding Is Reshaping the Economics of Software and Services

Leena Munjal headshot

Leena Munjal

VP Program Director

Gartner

Stephen Makin headshot

Stephen Makin

Sr. Research Director

Gartner

Participation is limited to qualified members. Please contact Zander Peterson (zander.peterson@gartner.com) to reserve your seat.

AI agents and agentic coding are reshaping software economics, pushing CIOs to reassess modernization and sourcing strategies. As providers shift their models, CIOs must decide where to invest, what to buy, and what to bring back in‑house in an uncertain and evolving environment.

This Executive Boardroom, led by Gartner Research Board, will explore:

  • How AI‑driven and agentic development models are reshaping application modernization decisions
  • The evolving value proposition and economics of software and service providers
  • How CIOs are recalibrating build‑vs‑buy strategies in response to the changing landscape

11:55am - 12:30pm  Lunch Service

12:30pm - 1:05pm  Keynote

AI Authority Drift — Closing the Governance Gap

Artificial intelligence is entering a new phase. No longer limited to generating insights, modern AI systems are beginning to act — initiating workflows, interacting with applications, and making decisions at machine speed. As agentic AI systems become operational participants inside enterprise environments, this session explores how enterprises can safely scale AI by establishing governance across identity, authority, behavior, and data, while enabling innovation without introducing unmanaged risk.

Attendees will learn:

  • How to control the authority, behavior, and data access of autonomous systems operating across complex digital ecosystems
  • The emerging governance model, enacted through a real-time control plane, to address authority drift, misconfigured permissions, and unintended AI behavior
  • A practical framework and architecture for governing AI at enterprise scale

1:05pm - 1:30pm  Break

1:30pm - 2:15pm  Breakout Session

Unifying Intelligence — The CIO's Playbook for Enterprise AI Colleagues

As AI assistants proliferate across enterprise platforms, CIOs face mounting challenges: fragmented intelligence, siloed data, and inconsistent governance that threaten innovation and measurable business outcomes. The answer isn't just integration—it's transformation. By deploying AI colleagues across back-office operations, CIOs can operationalize AI to modernize the application portfolio, strengthen cybersecurity, and drive enterprise-wide innovation. With the right architecture, AI colleagues don't just augment work—they automate it at scale, turning disruption into opportunity even amid competing priorities and resource constraints.

Join this session to explore:

  • Architecting a seamless, enterprise-wide agentic AI layer for operations
  • Breaking down silos to unlock cross-functional innovation and measurable value
  • Ensuring robust governance, security, and risk management with enterprise AI

1:30pm - 2:15pm  Breakout Session

10-Minute Wins

Adam Garey headshot

Adam Garey

SVP & CIO

COUNTRY Financial

Alyssa Moy headshot

Alyssa Moy

CIO

Option Care Health

Why learn from one peer when you can learn from three? In this unorthodox—but highly effective—breakout session, you’ll hear from multiple members of your community. Each speaker will take the floor for 10 minutes to share the most valuable lessons they’ve gleaned from their time in leadership.

1:30pm - 2:15pm  Executive Boardroom

Architecting the Future — Operationalizing AI for the New Customer Experience

Tony Sorensen headshot

Tony Sorensen

CIO

Five9

Ram Mullapudi headshot

Ram Mullapudi

CIO, Consumer Group

Rust-Oleum

Jonny LeRoy headshot

Jonny LeRoy

CTO

Grainger

AI and automation are no longer just tools for efficiency; they’re central to shaping enterprise strategy. By embedding AI into core processes, organizations can transform customer engagement, empower employees, and drive measurable business outcomes.

Join this boardroom session to discuss:

  • Accelerating enterprise operations with AI-driven automation
  • Elevating customer experience by responding to changing business needs
  • Scaling transformation securely with compliant, AI-enabled solutions

1:30pm - 2:15pm  Executive Boardroom

Stop Piloting, Start Producing — Operationalizing AI for Real Enterprise Value

Abishek Gupta headshot

Abishek Gupta

CPO

Retool

CIOs are navigating a new era where building AI prototypes is fast and accessible but maturing them into enterprise‑wide capabilities demands new strategies. How can business-driven innovation be scaled without creating tomorrow’s legacy debt?

Join this boardroom to discuss:

  • Turning rapid AI pilots into resilient, scalable solutions
  • Co-owning initiatives across the business while protecting core systems
  • Shaping the CIO’s influence as AI transforms enterprise leadership

1:30pm - 2:15pm  Gartner Boardroom

Gartner Client Boardroom

Kathy Ameche headshot

Kathy Ameche

VP, Executive Partner

Gartner

Open to Gartner Clients Only - Please Contact Zander Petersen (zander.petersen@gartner.com) to Reserve Your Seat. 

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

Building Adaptive Teams—Managing Change and Opportunity

 Explore how organizations can effectively navigate talent and change management by upskilling their IT workforce to meet the demands of tomorrow’s technology landscape.

3:00pm - 3:45pm  Executive Boardroom

From Firefighting to Fireproofing — Building Preemptive Security in the Age of AI

Tal Kollender headshot

Tal Kollender

CEO

Remedio

AI is reshaping the economics of cyber risk. Attack surfaces are expanding, threats are accelerating, and traditional reactive security models are reaching their limits. Today, risk stems not only from external adversaries but also from the rapid adoption of internal AI tools—often deployed with excessive permissions and limited oversight. How can organizations move from incident response to preemptive cybersecurity, identifying and addressing vulnerabilities before they’re exploited?

In this session, you will learn how to:

  • Build resilience at scale with proactive security measures
  • Reduce operational friction by addressing vulnerabilities early
  • Shift from constant firefighting to engineered fireproofing

3:00pm - 3:45pm  Executive Boardroom

AI-Ready Data History — Scalable Access and Governance

Tal Yalon headshot

Tal Yalon

VP Solutions Architecture

Eon.io

AI initiatives rarely stall due to a lack of tools; they stall when teams can’t reliably access, trust, or use the data they already own. For many enterprises, the richest records are found in data history, yet this data is often locked away, costly to retrieve, and difficult to govern across accounts, regions, and platforms. What opportunities can CIOs create by making historical data easily usable and accessible—even during outages or disruptions?

In this session, you will learn how to:

  • Enable data history for AI without rebuilding pipelines
  • Implement scalable governance and ensure resilient data access
  • Minimize duplication to control growth and reduce costs

3:00pm - 3:45pm  Executive Boardroom

AI Adoption Realities — Failures and Fixes

Corrado Azzarita headshot

Corrado Azzarita

Global CIO

Kraft Heinz

Every CIO has an AI project that didn’t go as planned—but those stories rarely get told. Let’s swap real-world experiences and uncover the lessons that turn setbacks into future success.

Join this boardroom to discuss:

  • Identifying root causes of AI project failures
  • Sharing practical recovery strategies and pivots
  • Building a culture of transparency and peer support

3:45pm - 4:00pm  Networking Break

4:00pm - 4:35pm  Keynote

Shifting Gears — Realizing Value With AI

Sean McCormack headshot

Sean McCormack

CIO

First Student

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

May 12, 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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Community Program Manager

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

Zander Petersen

Community Program Manager

971-499-8162

zander.petersen@gartner.com