CDO Magazine’s exclusive Chicago Executive Boardroom Dinner at STK Steakhouse on June 22 brought together senior data, analytics, and AI executives for an evening of candid peer exchange centered on the theme, “Reimagining Data Readiness with AI.” As organizations accelerate AI adoption, the discussion focused on what it truly takes to become AI-ready—from trusted data and semantic context to governance, enterprise architecture, and meaningful collaboration across the business. 

Executives openly shared real-world challenges, practical lessons, and emerging strategies for strengthening data readiness while scaling AI responsibly. Conversations highlighted the growing importance of semantic layers, connected data, and governance as the foundation for trustworthy AI and better business outcomes.

“It was certainly a different Executive Boardroom dinner this time where not only several members spoke out, the transparency with various partners and members was key,” Patrick Chew, AIT Worldwide Logistics VP, AI & Data Science, reflects. 

“There were genuine concerns about certain challenges and ambiguity expressed and as experienced in our latest AI journey. Several members were very candid and keen to hear each other’s thoughts and how they were addressed. These sort of community sharing and exchanges are invaluable!” Chew adds. “Thank you for not only showing up but also for all of these vital knowledge exchanges which keeps us relevant and abreast with this fast changing AI arena.”

For Anusha Dwivedula, Morningstar Director, Product Management Analytics, what struck the most was the conversation around semantic management. “As new semantic layer capabilities emerge, the market quickly responds with claims of compatibility and support. The harder question is trust. How do organizations verify that business meaning, governance, and context are preserved consistently across platforms? In the AI era, semantic consistency is becoming just as important as data quality because even the most advanced models are only as reliable as the definitions and context behind the data they consume,” Dwivedula observes.

According to Sabry Loganathan, Peloton Sr. Director, Enterprise AI Engineering, “To win the Enterprises AI game, we not only need to focus on the MCP layer to integrate with enterprise applications, we also need to focus on creating MCD – Meaningful Connected Data of the enterprise.”

Lexy Smith, CDO Magazine Community Director, highlights, “The dinner was one of the most candid rooms I have been part of all year. What struck me most was the exchange going both ways: attendees pressed Quest’s team on how they actually approach problems, and Quest turned the question back to the room. By the end of the night, both sides left with a clearer view of how the other approaches data solutioning, and that kind of mutual exchange is exactly what we hope these dinners create.” 

Summing it up, Susan Laine, Quest Software Chief Field Technologist, says, “What a fantastic Executive Boardroom Dinner in Chicago this week. It was refreshing to hear and see executives openly share their current concerns and perspectives on reimagining data management with AI, for AI. We see a growing emphasis on the importance of ontologies and context to enable a strong and effective semantic layer.”

Special thanks to Quest Software for making the CDO Magazine Chicago Executive Boardroom Dinner such a resounding success.

*Patrick Chew is a member of the CDO Magazine Global Board. 

Executives attending the CDO Magazine Chicago Executive Boardroom Dinner included: 

Michael C. Baker, NielsenIQ VP, Data Science Consumer Data, Advanced Analytics & AI; Dhruv Baronia, Northern Trust SVP, Head, Analytics Wealth Management; Kalyani Boddupalli, Double Good VP, Business Applications Data & Analytics; Patrick Chew, AIT Worldwide Logistics VP, AI & Data Science; Michael Colella, AXS Sr. Director, Global Data Strategy & Analytics (Head for US, CA & Japan) Product & AI Builder; Sarah Cook, i.c.stars Development & Special Events Manager; Dan Cromer, Walker & Dunlop (Former); Dennis Demandaco, Gallagher Business Intelligence Specialist Lead; Kathryn Dimmic, Cooley LLP Sr. Business Data Manager Innovation; Ivana Donevska, BMO Head, Enterprise Data & Analytics Risk; Anusha Dwivedula, Morningstar Director, Product Management Analytics; Don Fleschut, Ryerson VP & Chief Data Officer; Michael LaRue, University of Illinois Chicago Deputy Director, Software Delivery & Data; David Lee, Cushman & Wakefield Director, IT Audit & Data Analytics; Sabry Loganathan, Peloton Sr. Director, Enterprise AI Engineering; Shuen Mei, Harbor Capital Advisors VP, Director, Software & Data Engineering, Cait Moran, The Goodyear Tire & Rubber Company Global Head, AI; Sandeep Nema, Cook County Director, Head of Enterprise Architecture; Rooshana Purnyn, Former Hyatt Director, Data, AI Architecture & Platform Engineering; Sid Raina, Medline VP, AI & Data Analytics; Aukje Rijpkema, Clayco Director, Enterprise Applications; Farhan Sabzaali, University of Chicago Data & Analytics Leader; Kaitlyn Sawyer, Merrill Lynch Wealth Management; Frank Sung, Loop Capital VP, Data Management; Susan Thomas, Cooley LLP Business Data Manager; George Wang, FinTank Chief Information Officer; Kira Bolton, Quest Strategic Account Executive; Susan Laine, Quest Chief Field Technologist; Chris Post, Quest Strategic Account Executive; Michelle Smith, Quest Regional Strategic Sales Director; Anthony Losanno, CDO Magazine Managing Director; Corey Maxner, CDO Magazine Sr. Director, Community & Operations; Alexandra (Lexy) Smith, CDO Magazine Community Director; John Vulopas, CDO Magazine Account Director.