AI in Practice | AI & the Human Experience

We're gathering 75+ New England CEOs and executives around one question: when should AI make the call, and when should humans?

Boston

Thursday, October 22

6:00 PM - 8:00 PM

WithCoverage

Host

Speakers

Craig Breslow

Chief Baseball Officer @ Boston Red Sox

Manish Vora

CEO & Co-Founder @ Figure8 / Museum of Ice Cream

Max Brenner

Co-Founder & CEO @ WithCoverage

Space is limited. RSVP is required.

An evening on AI, connection, and what stays human

Hosted at the Museum of Ice Cream in partnership with Boston Seaport by WS Development, the evening's centerpiece is a conversation between Craig Breslow, Chief Baseball Officer of the Boston Red Sox, and Manish Vora, Co-Founder & CEO of Museum of Ice Cream, moderated by WithCoverage Co-Founder & CEO Max Brenner. They'll dig into how the Red Sox are using AI to make smarter decisions, and what every business can learn about where AI should lead and where the human experience still wins. Then the room weighs in with a quick round of "Human or AI?", voting on real leadership calls.

Evening Agenda:

6:00–6:30pm | Welcome reception
6:30–7:00pm | Speaker conversation + "Human or AI?"
7:00–8:00pm | Drinks, bites, ice cream & connection

Attendees: 75+ CEOs and executives from across New England. Full RSVP list will be shared in advance.

Space is limited. RSVP required.

Speakers

Craig Breslow

Craig Breslow is Chief Baseball Officer of the Boston Red Sox, where he leads all aspects of baseball operations. A former Major League pitcher, Craig spent 12 seasons in the MLB and was part of Boston’s 2013 World Series championship team before transitioning into the front office. Prior to joining the Red Sox leadership team, he spent five years with the Chicago Cubs, helping build and implement data-driven processes across baseball operations and player development. A Yale graduate in molecular biophysics and biochemistry, Craig brings a unique perspective on the intersection of data, technology, leadership, and human performance.

Manish Vora

Manish Vora is the co-founder and co-CEO of Museum of Ice Cream, the immersive experience brand he built with Maryellis Bunn from a 2016 pop-up into a global network of "experiums" that has welcomed over 2.5 million visitors and partnered with brands like Amex, Target, and Sephora. He is a Yale graduate and former investment banker.

Max Brenner

Max is the Co-founder & CEO of WithCoverage, a modern insurance and risk platform backed by Sequoia and Khosla Ventures ($42M+ raised). Previously he disrupted the financial advisory industry and built Compound into a $3B+ AUM digital family office platform.

What To Expect From The Evening

Invite-only group of experienced leaders

~75+ CEOs and executives from across New England, all actively thinking about how AI impacts their businesses and portfolios

Operator-led perspectives

Hear how the Red Sox front office and the team behind Museum of Ice Cream decide where AI leads and where people still make the call

Targeted connections

Attendees will receive the RSVP list ahead of the event to facilitate relevant, peer-level conversations

AI & the Human Experience

AI is changing how companies build, operate, and connect with customers. We’ll explore where it is creating real leverage across brand, customer experience, and operations, and where human creativity, judgment, and connection still matter most

Have Questions?

The Circle is an invite-only community of founders, operators, and investors, hosted by WithCoverage. We bring together small groups of leaders throughout the year for curated dinners at top restaurants across the U.S. There’s no membership fee or formal commitment - just the opportunity to join future gatherings and connect with peers you’d value most. In addition to the core community, we host both focused groups (e.g., consumer, hospitality, tech, investor) and broader gatherings - like AI in Practice - to bring together leaders navigating shared themes across industries.

Join Us For This Event

Space is limited. RSVP is required.