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

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

Louis DeStefano

Chief Growth Officer,
Oscar Health

Louis DeStefano is the Chief Growth Officer at Oscar Health, where he has been a driving force behind the company’s expansion from three states and 90,000 members in 2017 to a nationwide presence serving approximately 2 million members in 2025. Under his leadership, Oscar’s revenue has surged from $229 million in 2017 to $9.2 billion in 2024.

Louis leads Oscar’s growth organization where he oversees sales, marketing, sales operations, and product marketing. He is responsible for driving growth across ACA, ICHRA, and ancillary products.With a focus on individualized health coverage, he specializes in delivering solutions that serve both government-subsidized consumers and employer-sponsored members.

Before joining Oscar, Louis spent 13 years at UnitedHealthcare, most recently serving as Vice President of Sales and Account Management for the Northeast region. In this role, he managed a 500,000-member fully insured business, spearheading initiatives in growth strategy, product development, underwriting, risk management, and alternative distribution.

Beyond his corporate leadership, Louis has consulted for healthcare technology startups such as Nava, Garner, Invoy, and Budgie, helping to drive innovation in the industry.

Louis also serves as a mentor for Beat the Streets NY and is a board member of Westfield PAL. He holds a bachelor’s degree in Finance from Villanova University.

Jon Van Der Veer, DO

Founder & CEO,
Hy-Vee Health

Dr. Jon Van Der Veer is a nationally-recognized physician, innovator, and healthcare disruptor on a mission to reimagine how care is delivered and financed in America. He is the founder and CEO of Hy-Vee Health Exemplar Care, a growing direct primary care (DPC) and 24/7 urgent care model that gives patients access to the effective, affordable healthcare they deserve.

Dr. Jon launched Exemplar Care to deliver what traditional systems couldn’t: compassionate, whole-person care that prioritizes the time to build a strong patient-physician relationship. His partnership with Hy-Vee, one of the nation’s largest retail grocers, has brought this model to communities across the Midwest to deliver better health outcomes, lower costs, and happier patients.

Dr. Van Der Veer is certified by the American Board of Internal Medicine. Before starting his own practice, he served as chief medical officer at both Greene County Medical Center in Jefferson, Iowa, and CareMore Health in Des Moines, Iowa. Dr. Van Der Veer also worked as a primary care provider at UnityPoint Clinic Internal Medicine in Des Moines.

Earning his medical degree at Des Moines University College of Osteopathic Medicine, Dr. Van Der Veer completed his residency in internal medicine at Central Iowa Health System – Methodist in Des Moines. In addition to his clinical work, he is the co-author of several medical journal articles.

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

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.

Louis DeStefano

Chief Growth Officer,
Oscar Health

Jon Van Der Veer, DO

Founder & CEO,
Hy-Vee Health

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