Behind-the-scenes: How Oscar turned member obsession into an operating model | hioscar Blog | Oscar
Behind-the-scenes: How Oscar turned member obsession into an operating model
How Oscar uses continuous listening and data insights to personalize the member journey.
Oscar CommentaryOscar Tech & Product
6 min read
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For decades, health insurers have largely organized themselves around functions: claims, provider networks, enrollment, utilization management, customer service. Each department owns a piece of the member journey. Few own the experience itself.
Oscar has taken a different approach. While nearly every company says it is "customer-centric," Oscar has built an organization where understanding members isn't confined to an annual survey or call center dashboard. Instead, a dedicated Member Experience team sits alongside research, marketing, operations, and the frontline Care Team, translating what members experience every day into decisions that shape the business.
It's an organizational capability that remains surprisingly uncommon across healthcare.
“At Oscar, everyone is responsible for the member experience, and we believe that mindset should be embedded in every operating plan,” said Amanda DeBrule (opens in new tab), vice president of member experience at Oscar. “Our dedicated Member Experience organization has two arms. Member Experience Strategy focuses on member insights, product consulting, program management, and strategy. Member Tech builds and operates the technology that powers the member experience, from the app and enrollment to communications, support, and benefits configuration. Together, these teams partner closely with research, data science, marketing, and our frontline Care Team to continuously improve the experience for our members."
Seeing the whole person instead of isolated interactions
One of the biggest challenges legacy health insurers are trying to tackle today is bringing together every member interaction to understand the experience as a whole, rather than as a series of disconnected events. They’re just not built for it. Because we've built much of our technology stack ourselves, we can connect data across the member journey in ways that are difficult for insurers relying on decades-old, fragmented systems.
A member may shop for coverage online, receive text reminders, visit a physician, pay a premium, message customer support, and search for providers – all within a matter of days. At many healthcare organizations, each interaction lives inside a different system, owned by a different department.
Oscar's approach is different. We bring together enrollment information, health status, digital engagement, communications, care interactions, and operational data to build a continuously evolving picture of each member.
“It’s a living, breathing member profile, constantly updated with new information to reflect a member’s current health status and journey,” said Tory Grimley (opens in new tab), director of product at Oscar.
That holistic understanding allows teams to answer practical questions:
When is the best time to communicate with a member?
Should that communication arrive as a text, email, or phone call?
What information will actually help that individual make a healthcare decision?
Instead of treating every member the same, the experience adapts to the context of each person's journey. This unified view of members allows Oscar to determine the most effective communication channel (think: text, email, or a phone call), and the optimal timing for each individual member. This ensures that members receive the right message at the right time, replacing generic, impersonal outreach with a more seamless and personalized experience.
Small insights. Big changes.
Some of Oscar's biggest product improvements begin with seemingly small observations. While prior authorizations are one of our larger call drivers, we noticed that members often weren’t aware that prior authorizations expire. While we tackled broader prior authorization transparency across the member experience, the team also introduced proactive reminders before an authorization expires. Since launching in April, many of the members who received a reminder have already requested a new prescription authorization, helping them avoid disruptions at the pharmacy and creating a more proactive, transparent experience.
This approach, rooted in continuous member listening and data-driven insights, is especially critical when healthcare regulations shift. When enhanced ACA subsidies were set to expire, Oscar’s continuous analysis allowed the team to detect member confusion in near real-time. By analyzing inbound conversations, Oscar identified that members were specifically concerned about how monthly premiums would change, what the "eligibility cliff" meant for their specific plans, and the urgency of re-enrolling. Instead of waiting for survey results, Oscar acted immediately, augmenting generic regulatory notices with targeted, plain-language messaging that clearly explained a member’s options and step-by-step instructions to prevent coverage gaps.
Taking personalization to the next level
Many organizations define personalization as putting someone's first name into an email. Oscar thinks about it differently because members don't all experience healthcare in the same way.
“A Bronze plan member has different needs and expectations than someone enrolled in a Silver CSR plan,” explained Tali Goldstein (opens in new tab), director of Member Experience Strategy at Oscar. “One thing we have learned is that Spanish-speaking members often interact differently with providers than English-speaking members. Even seemingly small factors like whether someone is enrolling with us for the first time or renewing existing coverage can influence the support they need throughout their healthcare journey. Those differences may seem trivial but these types of nuances are the foundation for designing better experiences.”
Rather than building one digital journey for everyone, Oscar is investing in the technology and organizational capabilities needed to support increasingly personalized experiences as new products and member segments emerge.
As Goldstein explains, personalization at Oscar isn’t simply language translation. It's understanding how different populations navigate healthcare and designing experiences that reflect those differences.
Measuring what actually matters: From resolving issues to preventing them
Healthcare organizations often measure success through operational efficiency. For our part, Oscar tracks all the common metrics like engagement, feature adoption, and retention. But we are increasingly asking a more meaningful question: Did the member make a better healthcare decision?
Oscar evaluates whether members follow recommended care pathways, choose appropriate providers, engage with personalized guidance, and ultimately experience less friction navigating care.
“One internal metric rewards reducing unnecessary inbound interactions – like call center volume or messaging the care team – not because fewer conversations are inherently better, but because the ideal experience is one where members don't need to ask for help in the first place,” Goldstein explained.
It's a subtle shift where success isn't measured by how many problems member experience solves and is instead focused on how many problems members never encounter.
Setting a higher standard for member experience
Perhaps Oscar's most distinctive philosophy is who it considers its competition. The benchmark isn't another health plan. It's every digital experience consumers interact with every day.
"We're not benchmarking ourselves against other health insurance companies," Grimley said. "We're benchmarking ourselves against the best consumer apps. Finding a provider should be as easy as finding a restaurant or ordering dinner through Uber Eats."
That consumer mindset shapes everything from our rigorous, weekly usability testing to the conversational AI experiences that help members understand costs, compare care options, and navigate healthcare in natural language. As Grimley describes it, testing is central to Oscar’s process: “We regularly invite members to test prototypes and attempt to complete specific tasks, using their feedback to refine and perfect the experience before it ever reaches a wider audience,” she said.
Sustainable competitive advantage comes from organizational learning and not just technology
Technology, data and AI are all critical capabilities for companies today. But the more interesting story inside Oscar is organizational.
We have built mechanisms for continuously listening to members, translating those insights into product and operational decisions, and measuring whether those changes actually improve people's lives.
“In an industry still dominated by fragmented systems and siloed organizations, Oscar’s approach to member experience is our biggest competitive advantage,” DeBrule said. “We don’t just know more about our members. We have built an organization capable of learning from them every day.”
Disclaimer:
Oscar Medical coverage is underwritten by Oscar Insurance Company and its affiliates. Administrative Services for all plans provided by Oscar Management Corporation. All insurance policies and group benefit plans contain exclusions and limitations. This advertisement may be broadcast in states where policies and plans are not sold. For availability, costs, and complete details of coverage, contact Oscar at 855-672-2788.
