Healthcare Customer Experience at the Limit (The Derby Mill Series ep 30)

At the limit, healthcare CX may lead to super-capable medical agentic AI. The Derby Mill team discusses the implications with League CEO Michael Serbinis.

Jun 2, 2026

How are companies using AI to improve the healthcare journey for consumers? And how will things evolve at the limit, where wearable technology integrates with electronic medical records and medical agentic AI analyzes everything on the fly to issue recommendations and improve outcomes? In other words, what are the implications of everyone becoming equipped with their own superhuman medical agent?

Seen one way, a superhuman medical agent is what League is aiming to develop. Founded in 2014 in Toronto, League operates an AI-powered healthcare platform for insurance companies and other payers or providers. The platform allows users to manage health benefits as well as their own healthcare. As of early 2026, the company has more than 60 million contracted users and more than a billion consumer interactions annually. Customers include Highmark Health, Manulife, Shoppers Drug Mart, and Medibank. Last year, League gave 100 million healthcare recommendations, of which people clicked through or followed through about 65% of the time.

In this episode, the Derby Mill team explores where League’s technology might go at the limit with League founder and CEO Mike Serbinis, who aims to expand the company’s capabilities to create a 24/7 infinite care platform—basically, an all-knowing doctor who knows as much as possible about you, your healthcare data, and the science of medicine. It’s a fascinating conversation that sees Sendhil observing how little the medical profession currently knows about optimizing health, or patients themselves, and Ajay challenging Rich to decide whether superhuman AI doctors would be better than having a doctor as a spouse today. (Rich says yes.)

More on our guest: A serial entrepreneur, Michael Serbinis has also founded and run Kobo, the digital reading company, cloud storage pioneer, DocSpace, and Critical Path, a messaging service. Serbinis is chair of the board for the Perimeter Institute and on the board at the Vector Institute for Artificial Intelligence. He sits on Canada's AI Strategy Task Force.

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HOSTS AND PANELLISTS

Mike Serbinis, founder and CEO, League
Ajay Agrawal, co-founder and partner, Intrepid Growth Partners
Richard Sutton, senior advisor, Intrepid Growth Partners, 2024 Turing Award recipient, pioneer of reinforcement learning and professor, University of Alberta
Sendhil Mullainathan, senior advisor, Intrepid Growth Partners, MacArthur Genius grant recipient and professor, MIT
Niamh Gavin, senior advisor, Intrepid Growth Partners, Applied AI scientist and CEO, Emergent Platforms
Suzanne Gildert, CEO, Nirvanic Consciousness Technologies, quantum physicist, co-founder of Sanctuary AI and Kindred

LINKS

League website. League explainer video. League on X.

Subscribe to The Derby Mill Series at our Substack (main site) or on YouTube, Spotify or Apple Podcasts

Derby Mill is created by the team at Intrepid Growth Partners and produced by Ghost Bureau.

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DISCUSSION POINTS

00:00 Cold open

00:38 Introductions

01:19 League explainer

01:55 Serbinis explains League

05:28 League’s AI today

08:09 More AI: Content recommendations

12:00 League’s data inputs

13:55 AB testing

19:10 Healthcare archetypes

22:15 Max health v. max engagement

25:30 Business model

27:00 At the limit: Rich

29:00 Married to a doctor

29:42 At the limit: Sendhil

31:10 Healthcare becomes you

33:37 ROI is huge

38:06 Suzanne: Robot paramedics

42:53 Serbinis responds

46:20 Infinite care team

49:16 Sendhil’s wrap up

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NUGGETS

How League can 10x engagement for its clients (and improve user outcomes)

League CEO Michael Serbinis explains

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How customer archetypes help League optimize engagement

Sendhil asks CEO Michael Serbinis to break it down

A Superhuman AI Medical Agent

Ajay, Rich and Michael Serbinis discuss League at the limit

Inverting the Medical System

Sendhil Mullainathan imagines League at the limit

All-Knowing Robot Paramedics

Suzanne Gildert imagines League at the limit

DISCLAIMER

The content of this podcast is for informational and educational purposes only and should not be construed as marketing, solicitation, or an offer to buy or sell any securities or investments. The opinions expressed in this video are those of the participants and do not necessarily reflect the views of Intrepid Growth Partners or its affiliates. Any discussion of specific companies, technologies, or industries is for illustrative purposes and does not constitute investment advice. Viewers are encouraged to consult with their own financial, legal, and tax advisors before making any investment decisions.

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The Derby Mill Series: Pushing AI to the Limit

Intrepid Growth Partners’ Senior Advisors Rich Sutton (pioneer of reinforcement learning), Sendhil Mullainathan (MacArthur Genius recipient), Niamh Gavin (Applied AI scientist) and Suzanne Gildert (CEO, Nirvanic Consciousness Technologies) join Intrepid partner and co-founder Ajay Agrawal to explore the latest threads in the AI community.

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