Leaders in AI Summit Chicago 2026

Afternoon Networking Break

Networking · Editorial classification · Sep 15, 2026

Published schedule: 2:30 PM - 3:15 PM.

Cocktail Hour

Networking · Editorial classification · Sep 15, 2026

Published schedule: 5:00 PM - 6:00 PM.

Executive Roundtable Discussions

Other · Editorial classification · Sep 15, 2026

Published schedule: 4:00 PM - 4:45 PM.

From AI Activity to Accountability: The New Path to AI ROI

Workshop · Sep 15, 2026

Published schedule: 3:15 PM - 4:00 PM. Most organizations can measure AI adoption. Far fewer can explain whether AI is creating meaningful business value. As enterprise investment accelerates, leaders need a way to connect AI usage with workforce productivity, operational outcomes, governance, and measurable ROI.‍This workshop explores how organizations can move beyond basic adoption metrics to understand where AI is delivering business impact, where workflows remain constrained, and how workforce intelligence can guide future AI investments. Using practical examples from enterprise deployments, attendees will learn how continuous visibility into work helps identify adoption patterns, operational bottlenecks, governance gaps, and opportunities to redesign work, not simply automate existing processes.

• Bruce Monaco
• Gabriela Mauch

Intimate Think Tank Dinner - Invite Only

Networking · Editorial classification · Sep 15, 2026

Published schedule: 6:00 PM - 9:00 PM.

Pre-Summit Workshop Hotel Check-In

Other · Editorial classification · Sep 15, 2026

Published schedule: Begins at 12:45 PM. We recommend checking in at Westin Michigan Avenue Chicago before 12:30 PM to give yourself time to settle in and get oriented ahead of the day’s programming. While there’s no formal check-in window and we understand travel schedules may vary, early arrival is encouraged to ensure a smooth start.For any questions regarding your stay or early check-in assistance, please contact the Westin Michigan Avenue Chicago front desk directly or connect with our team onsite.

Present Your executive roundTables Findings

Other · Editorial classification · Sep 15, 2026

Published schedule: 4:45 PM - 5:00 PM.

Registration & Networking

Registration · Editorial classification · Sep 15, 2026

Published schedule: Begins at 1:00 PM - 1:30 PM. Upon arrival between 1:30 PM and 2:00 PM, please proceed directly to our registration area to check in. Simply provide your name and confirmation details at the welcome desk, where you'll receive your event badge and session materials. Once checked in, you’ll have time to meet fellow attendees and orient yourself before sessions begin promptly at 2:00 PM. Our onsite team will be available throughout the registration window to assist with any questions or special requests.

Sovereign AI in the Age of Agents: Architecture, Control, and the Economics of Autonomy

Workshop · Sep 15, 2026

Published schedule: 1:30 PM - 2:30 PM. Sovereign AI has become one of the most discussed concepts in enterprise technology. But what does sovereignty actually mean when your AI systems are autonomous agents? Agents consume tokens at 15-50x the rate of chatbots, make decisions regulators will scrutinize, and interact with your enterprise data in ways most architectures were never designed for. This workshop presents a five-dimension framework for sovereign AI in the agentic context: compute sovereignty, token sovereignty, data sovereignty, decision sovereignty, and operational sovereignty. Each dimension maps to specific architecture decisions, from right-sizing across the full infrastructure stack to preparing enterprise data for agent-native consumption. Grounded in token economics analysis showing up to 18x cost advantages through infrastructure ownership and real-world deployment architecture from regulated industries, this session gives enterprise leaders a practical framework for maintaining control as agentic AI moves into production environments.

• Allen Holmes
• Bruce Monaco

Afternoon Networking Break

Networking · Editorial classification · Sep 16, 2026

Published schedule: 2:30 PM - 3:30 PM.

Arrivals & REGISTRATION

Registration · Editorial classification · Sep 16, 2026

Published schedule: 8:30 AM - 9:00 AM. Start your Leaders In AI Summit experience by checking in at the Leaders in AI Summit hosted at the luxurious Westin Michigan Avenue Chicago in Chicago, Illinios. Our VIP Registration Team will greet you in the lobby with your VIP badges and a complimentary gift bag. Enjoy artisian coffee, tropical fruit, and pastries while you prepare for an exciting day of insights and exclusive networking.

Closing Remarks

Other · Editorial classification · Sep 16, 2026

Published schedule: 4:50 PM - 5:00 PM.

Cocktail Hour

Networking · Editorial classification · Sep 16, 2026

Published schedule: 5:00 PM - 6:00 PM.

Data Readiness for the Agentic Enterprise: Building the Trusted Foundation for Enterprise AI

Panel discussion · Sep 16, 2026

Published schedule: 3:30 PM - 4:10 PM. Enterprise AI is entering a new phase. As organizations move beyond copilots toward autonomous agents capable of executing real business processes, success now depends on trusted enterprise data, effective governance, and production ready AI architectures rather than simply selecting the right foundation model.

• Bruce Monaco
• Stefan Kalb
• Zac Harlan

Executive Roundtable Discussions

Other · Editorial classification · Sep 16, 2026

Published schedule: 1:00 PM - 1:55 PM.

Intimate Think Tank Dinner - Invite Only

Networking · Editorial classification · Sep 16, 2026

Published schedule: 6:00 PM - 9:00 PM.

Lunch Hosted By the institute for ai transformation

Break · Editorial classification · Sep 16, 2026

Published schedule: 12:10 PM - 1:00 PM.

Navigating the Human element of AI

Panel discussion · Sep 16, 2026

Published schedule: 4:10 PM - 4:50 PM. Enterprise AI adoption isn’t about quick wins or one-off pilots — it’s about the hard-earned lessons that transform experimentation into real business impact. This fireside chat cuts through the hype to explore what it actually takes to drive adoption across a complex organization. From standing up sandbox environments and leveraging synthetic data, to building frameworks for use case intake and collaborating with Finance on productivity-based ROI, this session offers practical insights on scaling responsibly. You’ll learn how to activate employees through grassroots programs like Office Hours and Hackathons, use AI to augment — not replace — teams, and unlock the hidden value of unstructured documents. Leaders will leave with actionable strategies for navigating cultural resistance, aligning stakeholders, and embedding governance that evolves alongside innovation.

• Bruce Monaco
• Ishu Gupta
• Jenna donoghue
• Nate Carson

Opening Networking Break

Networking · Editorial classification · Sep 16, 2026

Published schedule: 10:30 AM - 11:30 AM.

Opening Remarks

Other · Editorial classification · Sep 16, 2026

Published schedule: 9:00 AM - 9:10 AM. Kick off the summit with opening remarks from Robert Jaggers, CEO of the Institute for AI Transformation, as he introduces the themes and priorities for the day ahead. This brief session will lead into our opening panel, setting the focus for impactful discussions to follow.

Present Your executive roundTables Findings

Other · Editorial classification · Sep 16, 2026

Published schedule: 1:55 PM - 2:30 PM. Up next, each roundtable will share their key takeaways with the full audience. Please designate one representative from your table to go on stage and briefly present your group’s findings and discussion highlights.

The Enterprise AI Playbook for 2027: What Leaders Must Decide, Fund, & Stop Doing

Panel discussion · Sep 16, 2026

Published schedule: 11:30 AM - 12:10 PM. In an era of rapid disruption, organizations that neglect the human dimension of transformation fall behind. This dynamic panel of CXOs will reveal how people-centered approaches ignite progress, unite teams, and reinforce company culture. You’ll uncover practical methods to secure stakeholder buy-in, dismantle resistance, and foster an adaptable mindset that embraces ongoing evolution. Expect candid discussions on real-world success stories, alongside proven frameworks that keep your workforce energized and your organization moving forward.

• Ari Kaplan
• Bruce Monaco
• Dale Brown
• Scott garnick

THE MODERN AI STACK FOR BFSI: DATA READINESS, ENTERPRISE CONTEXT & AGENTIC AI

Panel discussion · Sep 16, 2026

Published schedule: 9:50 AM - 10:30 AM. Financial institutions are moving beyond AI copilots toward enterprise AI systems capable of orchestrating complex workflows across customer service, fraud detection, underwriting, compliance, software engineering, and internal operations. Success now depends on far more than selecting a foundation model... it requires trusted enterprise data, enterprise context, Model Context Protocol (MCP), APIs, orchestration frameworks, and production-ready infrastructure.This panel explores how leading financial institutions are modernizing their AI stacks, preparing enterprise data for intelligent systems, and deploying agentic workflows that securely connect AI to business applications while delivering measurable business value at scale.

• Arup Saha
• Asad Qureshi
• Bruce Monaco
• David Pierce
• Ron Simon

THE RACE FOR ENTERPRISE AI: AGENTS, INFRASTRUCTURE & EXECUTIVE DECISIONS

Panel discussion · Sep 16, 2026

Published schedule: 9:10 AM - 9:50 AM. AI initiatives hold the promise of transformation, yet many organizations struggle to move beyond pilot phases, leaving potential value unrealized. Research shows that the majority of AI pilots stall due to misaligned goals, resource limitations, and insufficient cross-functional buy-in. These challenges often lead to delayed ROI, wasted investments, and reduced stakeholder confidence. This panel will uncover the key reasons why pilots fail and offer actionable strategies to build scalable, enterprise-wide AI frameworks that deliver meaningful results.

• Bruce Monaco
• Dan Schneider
• Girdhar Agrawal
• John Encizo