.png){kind=logo}
A Curated Gathering
A room of peers, not a product pitch
An intimate dinner and roundtable for senior technology, data, security, and AI leaders across Massachusetts. No vendors selling. Off the record. Just candid, peer-to-peer conversation about what is working with AI, and what is not, over a world-class meal.
The Conversation
Three questions every leader is wrestling with
i.
Value
Where is the real ROI, beyond the efficiency trap, and how do we move from experiments to scale?
ii.
Risk
How do we scale AI without putting our data, our compliance, or our reputation on the line?
iii.
Speed
How do we avoid being part of the majority of AI projects that stall before they ever deliver?
The Evening
How the night unfolds
4:30 – 5:15
Cocktails & Social Time
5:15 – 5:30
Opening Remarks, presented by TeamShield Group
5:30 – 6:00
Cisco Fireside Chat: Closing the AI Execution Gap
6:00 – 7:00
Dinner (Tim Partridge, Legacy Club of Boston Executive Chef, curated menu)
7:00 – 8:00
Thought Leaders & Town Hall Discussion with Topics Including: “Successes, Challenges, Future of AI in practice of State Local Education, Government, Infrastructure, and the Innovation Economy”
8:00 – 8:30
Prodigy Labs: The senior leadership team of Prodigy Labs will provide an inside look at the journey, technology, and opportunity behind a new way to make the world’s most valuable human expertise personal and available at scale.
8:30 - 8:35
Closing Remarks, Chris Jennings
8:35 – 9:30
Optional Prodigy Lab open door Boardroom Demonstration.
9:30 – 10:00
Enjoy Legacy Club of Boston Amenities: Club’s Tournament Level Pool Table, Beacon Hill Pallor Dart Room, Access to the Private Red’s Victory Lounge with complimentary cigar, sample the Chris Voss private Bourbon selection.
10:00
Event Concludes
Panel Information
Thought Leaders & Town Hall Discussion with Topics Including: “Successes, Challenges, Future of AI in practice of State Local Education, Government, Infrastructure, and the Innovation Economy”
Cisco’s AI strategy bridges infrastructure, automation, and security.
Key solutions include AI Networking for scaling high-density clusters, Cisco AI Defense for securing models and guarding against threats like prompt injection, AgenticOps/AI Canvas for automated IT operations and Webex collaboration.
Prodigy Labs is an early-stage AI company exploring one of technology’s most exciting possibilities: scaling human experience.Using patent-pending behavioral modeling technology, Prodigy creates authorized digital twins that capture how accomplished experts think, make decisions, and communicate.
THE ATTENDEES
Thought Leaders, Distinguished Guests, & Attendees Include
Chris Jennings
(Moderator)
Co-Founder & President, TeamShield Group | LP at Boston Seed Capital | Board Member, Boston AI Week
Josh Jackson
Global AI Sales Leader @ Cisco
Devesh Srivastava, Ph.D.
Global AI Solutions Leader @ Cisco
Judah Phillips
Chief AI & Product Officer @ Market Holdings | Founder, Boston AI Week
John Holmes
Managing Director, Accenture Supply Chain & Engineering
Warren Bamford
Senior Advisor, The Edward Davis Company | Special Agent FBI 24 years, Financial & Organized Crime, Counter Terrorism. Former head of Global Security National Grid.
Jason Snyder
Secretary of the Executive Office of Technology Services and Security and Commonwealth CIO
Jeff Sampson
CEO & Co-founder, Prodigy Labs | Founder, Dread Pirate Group, 7x founder, ex-Microsoft, former VC
Chip Wilson
CFO & Co-founder, Prodigy Labs | Building the first Agentic Media platform, 9x CFO, former VC & Investment Banker
Steve Milton
Chief Scientist & Co-founder, Prodigy Labs | Founder, PlaceIQ | C-Suite Data & AI Technologist, Strategy & Scale
The Conversation
Who is in the room
Twenty-five qualified Massachusetts leaders across state and local government, K-12, and higher education. A special guest will be announced.
CIO
CISO
CDO
CTO
CAIO
Chief Innovation Officer
Director of AI Strategy
State & Municipal CIO
University VP for IT
The Setting
Legacy Club of Boston
Members Only
Easy to reach, directly across from TD Garden
A private members’ club at 180 Canal Street, directly across from TD Garden with its own private parking lot, so arriving is effortless. Inside: chef-driven dining, an elevated cocktail program, and a private room built for candid conversation.
The Experience
A bespoke menu, full club access, AI demo, Pool, Dart Room, Private cigar lounge behind a bank vault door
A multi-course dinner created for the evening, a boardroom demo area showcasing the latest in AI, and an open cigar lounge to close the night.
180 Canal Street, 5th Floor, Boston, MA 02114
Registration · Strictly Limited
Register your interest
Complete the form below to request a seat. We personally review every registration to keep the room curated, and we will follow up to confirm your place.
This is a personal invitation extended to you alone. Your seat cannot be shared, forwarded, or transferred to anyone else.
+
.png){kind=logo}
The Boston AI Executive Exchange · Thursday, July 30, 2026
Hosted by TeamShield Group & Cisco · chris@teamshieldgroup.com