NEW YORK — September 22, 2026 — Data, AI, technology and security leaders gathered at Club A Steakhouse in New York City for the CDO Magazine New York Executive Boardroom Dinner, sponsored by Oracle, for a candid discussion about an increasingly consequential enterprise question: When is AI trusted enough not just to inform a decision, but to make one?

Moderated by Paul Lilford, Director, Product Strategy AI and Analytics at Oracle, the evening’s discussion, “From Trusted Enough to Optimize — to Trusted Enough to Decide,” moved beyond AI experimentation to examine the data, governance, architecture and organizational foundations required as enterprises give AI greater responsibility.

From Trusted Enough to Optimize to Trusted Enough to Decide

As enterprises consider allowing AI agents to act rather than simply recommend, AI governance becomes inseparable from the question of trust.

The conversation began with perhaps the hardest question facing organizations deploying increasingly autonomous AI:

What would it take for you to trust AI with a decision that actually carries risk? Where in your enterprise would you trust an agent to act?

But trust was only one part of the equation.

Leaders were also asked to confront what happens when the data underneath AI remains fragmented and critical business semantics are still buried in spreadsheets and institutional knowledge:

Your data is fragmented. Your semantics are buried in spreadsheets and tribal knowledge. How are you solving for that — not in theory, but in practice?

The discussion then widened from individual AI implementations to enterprise scale:

The organizations that scale AI successfully and the ones that don’t — what actually separates them? And honestly, which side are you on right now?

The final questions put people and architecture at the center of the conversation. Leaders considered what a commitment to human augmentation over replacement actually looks like inside an organization, particularly for employees concerned about what AI means for their roles, and what single change to their data or AI architecture could have the greatest impact.

Taken together, the questions reflected a shift in the enterprise AI conversation. The challenge is no longer simply whether an organization can build or deploy AI. It is whether its data foundation, AI governance strategy, architecture and people are ready for AI systems entrusted with increasingly consequential actions and decisions.

Paul Lilford, Director, Product Strategy AI and Analytics at Oracle, moderates the discussion at CDO Magazine’s New York Executive Boardroom Dinner, challenging leaders to consider what it takes to trust AI with decisions that carry real business risk.

Different Industries, Similar Data and AI Challenges

The dinner brought together executives from organizations spanning financial services, energy, media, consumer products, government and other sectors.

For Shantanu Pal, CISO at Blackfein Scholes Capital, that diversity made the similarities among organizations particularly revealing.

“I enjoyed hearing the perspectives of people at companies of different sizes and industries, and realizing we all face similar challenges, and can learn from each other. The guided conversation surfaced interesting approaches that people were taking towards AI, data, and security.”

Pal’s observation underscored an important dimension of the evening: AI may be developing rapidly, but many of the challenges surrounding its enterprise adoption cut across company size and industry.

Questions of trusted data, agentic AI security, governance and how organizations move from experimentation toward practical implementation are increasingly shared challenges as AI systems gain greater autonomy.

Shantanu Pal, CISO at Blackfein Scholes Capital, shares his perspective during the New York Executive Boardroom Dinner as leaders compare approaches to AI, data and security across industries.

AI Is Only as Good as the Data Under It

For Jason Pope, Executive Vice President & Chief Technology Officer at Flagstar Bank, the conversation reinforced the relationship between AI ambition and the data foundation required to support it.

“What made last night at Club A valuable was hearing how other leaders and organizations are putting AI to work, not just talking about it. The theme in every conversation was the same one we lived at Flagstar: AI is only as good as the data under it. Modernizing our data first is what made our S2 Platform, Simple and Sophisticated, possible, and rooms like this one, thanks to CDO Magazine and Oracle, are where we learn what’s working and share what we’ve learned for the benefit of the larger data community.”

That distinction between talking about AI and putting it to work goes to the heart of the evening’s discussion. As AI assumes a greater role in enterprise workflows and decision-making, data modernization is no longer simply an infrastructure priority. The quality, accessibility and readiness of the underlying data directly influence how confidently organizations can put AI to work.

Jason Pope, Executive Vice President & Chief Technology Officer at Flagstar Bank, discusses the connection between data modernization and putting AI to work across the enterprise during CDO Magazine’s New York Executive Boardroom Dinner.

The Room New York Leaders Made Time For

Even getting to the dinner became part of the story.

The event coincided with the United Nations General Assembly, bringing motorcades, road closures and significant congestion across Manhattan. Yet executives still made their way to Club A, and according to Gerri Caveness, CDO Magazine Global Community Director, the commitment continued well after they arrived.

“Apparently, not even the United Nations can keep this incredible NYC community from a CDO Magazine dinner!! New York was gridlocked, motorcades were everywhere, and getting across Manhattan was virtually impossible. But they came.

Nobody was checking the clock, nobody was rushing for the door, and the conversations just kept going and going and going.

New York has a million places to be on any given night. Last night, this was the room. I am so honored to be part of this incredible community of tech rockstars.”

Data, AI, technology and security leaders continue the conversation at CDO Magazine’s New York Executive Boardroom Dinner, exchanging perspectives across industries on the foundations required to scale trusted enterprise AI.

Special thanks to Oracle for making the event a success.

Executives attending the CDO Magazine New York Executive Boardroom Dinner included:

• Tesa Brody, Bazooka Candy Brands Senior Digital Product Lead
• Lisa Cheng, JPMorgan Chase & Co Product Manager-Payment
• Stephanie Garland, State of Maryland Director of Data Literacy
• Vanessa Jones-Nyoni, Commerzbank Chief Data Officer North America
• Freda Liang, JPMorgan Chase & Co Product Manager, Bill Pay
• John Napoli, DTCC Head of Digital Client Platforms & IT Management
• Shantanu Pal, Blackfein Scholes Capital CISO
• Jason Pope, Flagstar Bank Executive Vice President & Chief Technology Officer
• Anil Prasad, Duke Energy Corporation Senior Software Engineering Leader, Software Products, Data, AI/ML, GenAI
• Lia Rogers, MSCI Head of Client Insights & Analytics
• Alex Rosenzweig, formerly American Express Director, Data AI Risk & Controls
• Namrata Shah, formerly Nuveen Managing Director, AI Adoption, Finance Transformation, Engineering CoE & Investment Technology
• Karen Swift, formerly Penske Media Corporation Vice President, Information Technology
• Loucas Tsiartas, Broadridge Financial Solutions Vice President, Sustainability Data, Strategy & PMO
• Aphrodite Brinsmead, Oracle Senior Product Marketing Manager, AI and Analytics
• Paul Lilford, Oracle Director, Product Strategy AI and Analytics
• Avi Sil, Oracle Senior Director, Applied Science
• Gerri Caveness, CDO Magazine Global Community Director
• Anthony Losanno, CDO Magazine Managing Director