How Oscar Health + Hy-Vee Are Building a New Local, Tech-Enabled Health Plan

Guests: 

• Louis DeStefano, Chief Growth Officer, Oscar Health

• Jon Van Der Veer, DO, Founder & CEO, Hy-Vee Health

In this special HLTH interview, Bright Spots in Healthcare host Eric Glazer speaks with two leaders shaping one of the most innovative payer–provider–retail collaborations in the country:

• Louis DeStefano, Chief Growth Officer, Oscar Health

• Jon Van Der Veer, DO, Founder & CEO, Hy-Vee Health

Together, Oscar Health and Hy-Vee Health are building a new kind of health plan, one that blends local access, convenient care, primary care-first design, and tech-enabled member experience. Think of it as a hybrid model: part direct primary care, part advanced digital platform, part community-rooted retail ecosystem.

This conversation dives into how the two organizations are integrating brick-and-mortar clinics, urgent care, pharmacy, SDOH-friendly retail access, and Oscar’s tech stack, including “Oswell,” Oscar’s AI-powered clinical support tool, to deliver a personalized and coordinated experience.

Topics We Cover:

• Why healthcare must be local, convenient, and relationship-driven

• How the partnership blends a supermarket chain, primary care clinics, and a tech-enabled health plan into one member experience

• How ICHRA is opening new doors for employer-driven personalization

• The role of AI and tools like Oswell in interpreting labs, improving communication, and augmenting care

• What a modern, scalable direct primary care model could look like

• The 10-year vision for this collaboration and where it expands next

This episode offers a first look into a payer–retail–provider model that could reshape consumer expectations, and redefine how employer-sponsored and individual coverage works in the coming decade.

References and Mentions:

• Learn more about the partnership between Oscar Health and Hy-Vee Health - https://www.hioscar.com/hy-vee-health

• Meet Oswell, Oscar Health's new health AI agent - https://www.hioscar.com/oswell 

• Dr. Garrison Bliss, widely recognized as the “Godfather of Direct Primary Care” -  https://www.linkedin.com/in/garrisonblissmd/

Bios:
Louis DeStefano: https://hlth.com/events/usa/speakers/2025/louis-destefano
Dr. Jon Van Der Veer: https://hlth.com/events/usa/speakers/2025/jon-van-der-veer

Partner with Bright Spots Ventures: If you are interested in speaking with the Bright Spots Ventures team to brainstorm how we can help you grow your business via content and relationships, email [e-mail]

About Bright Spots Ventures:

Bright Spots Ventures is a healthcare strategy and engagement company that creates content, communities, and connections to accelerate innovation. We help healthcare leaders discover what's working, and how to scale it. By bringing together health plan, hospital, and solution leaders, we facilitate the exchange of ideas that lead to measurable impact. Through our podcast, executive councils, private events, and go-to-market strategy work, we surface and amplify the "bright spots" in healthcare—proven innovations others can learn from and replicate. At our core, we exist to create trusted relationships that make real progress possible. Visit our website at www.brightspotsinhealthcare.com.

Visit our website:  www.brightspotsinhealthcare.com.

Follow Bright Spots in Healthcare: https://www.linkedin.com/company/shared-purpose-connect/