Why $3.2 billion Oscar Health pursued an unusual tech strategy for a startup insurer, according to the early employee who led the charge

Courtesy Oscar Health

Sara Wajnberg, 36, is the chief product officer at health insurance startup Oscar Health.
When Wajnberg joined about six years ago in Oscar’s early days, it was her first foray into healthcare.
She broke down some of the key lessons she learned while building Oscar’s technology product.
Wajnberg is one of Business Insider’s 30 leaders under 40 transforming the future of healthcare.
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When Sara Wajnberg, 36, joined health insurance startup Oscar Health in its early days six years ago, it was her first time working in healthcare.

Wajnberg, now the chief product officer at Oscar, had a background in working in product. Her sister was leading the product team at another company backed by Josh Kushner’s Thrive Capital and introduced her to the team. After meeting with Kushner, Wajnberg was in.

"I was pretty much sold immediately," Wajnberg said.

Wajnberg oversees the technology Oscar uses, from the app that members use to the technology the company relies on to process insurance claims. Oscar offers health insurance plans on the individual exchanges set up under the Affordable Care Act, plans for small businesses, and — in 2020 — Medicare Advantage plans. The startup was valued at $3.2 billion.

For her work, Business Insider named Wajnberg to our list of 30 healthcare leaders under 40 transforming the industry.

Building out Oscar’s technology platform, she’s learned a lot. For one, working within the regulatory constraints in healthcare was a new challenge for her. Plus, she’d often run into instances where she was limited in what she and her team could do by the constraints of other companies and the data they collected.

In particular, there were two main lessons she’s learned in her years there.

1. The experience won’t work if it relies on outside companies

Early on, Wajnberg and the team realized that there would be a lot they’d have to build themselves, rather than relying on outside services. Using outside companies for some functions is common in health insurance, but Wajnberg said that approach would hamstring Oscar, which is trying to create a more customer-friendly health insurer.

"The first thing that I think we learned very early on was that we wouldn’t be able to create the experience we envisioned by using a ton of third-party vendors," Wajnberg said.

Initially, the hope was to enlist third-party vendors that could take on the back-end work that comes with running a health insurer, like processing insurance claims. The hope was that Oscar could sit in the middle and show that information in a more consumer friendly way.

Instead, they ended up having to do it themselves.

"It turned out that we learned that we needed to own the full stack of operations to be able to deliver the experience we wanted," Wajnberg said.

2. Healthcare is human

Another big lesson Wajnberg learned during her time at Oscar: "Healthcare has such a big human component," she said.

That’s been key to the development of Oscar’s concierge service. Members are assigned a set care team that can help them navigate their insurance benefit as well as answer questions about their health.

By having a dedicated group to answer questions rather than a call line where members would have to repeat their issue to a new person each time, Oscar has been able to build up trust with its members.

"That has had a huge impact on trust level," Wajnberg said. "People want to feel like someone understands what they’re going through, they don’t have to repeat themselves over and over, and that they’re actually going to get help."

Wajnberg is one of Business Insider’s 30 leaders under 40 transforming the future of healthcare. Read the full list here.

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