kate
Simplifying Benefits
Redesigning Benefits & Coverage for Clarity and Action
Benefits & Coverage is one of Oscar Health's most visited and high-stakes member experiences, yet also one of the most confusing. As project lead and full-stack engineer, I drove the redesign of this experience to support a key company goal: improving retention by helping high-utilization members better understand and use their benefits, while reducing operational costs and reliance on support channels.
Partnering with product, design, and UX research, I translated complex insurance rules into a clearer, more actionable flow that helped members see what their plan covered, what it meant financially, and how to move to next steps in their care.
software engineer at Oscar Health
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Background
The Problem: Understanding Coverage
Members came to the Benefits page expecting to understand how their health plan works and to answer a few core questions:
What does my plan cover? How much will I pay? Where can I go?
This information was especially important for high-utilization members and those facing upcoming procedures, new diagnoses, or ongoing treatments.
The Problem
Despite strong overall digital engagement, satisfaction with the Benefits & Coverage experience remained among the lowest across Oscar's digital products. Operational data showed a high volume of contacts related to deductibles, coverage, and costs from members who had already visited the page, each carrying an avoidable support cost.
The Opportunity
As Oscar set stronger goals around retention and digital self-service, Benefits & Coverage emerged as a critical opportunity to better support members at these moments.
How might we make benefits and costs easier to understand, while connecting members seamlessly to the next step of care?
User Research & Insights
I worked closely with product, design, and UX research to understand why members visited the Benefits & Coverage page and where the current experience broke down:
  • Reviewed member feedback, support transcripts, and usage analytics to form an initial picture of common questions and failure points.
  • Ran “Tuesday Testers” usability sessions, observing members complete specific tasks in the existing experience to see where they hesitated, got stuck, or lost confidence.
What we heard
From the qualitative research, I grouped findings into common behaviors, pain points, and emotions to find user experience patterns:
  • Members came to the page with simple, high-stakes questions (“What’s covered?”, “How much will this cost?”, “Where can I go?”) but struggled to find a clear starting point.
  • They often described feeling overwhelmed and wanting to easily confirm that their next visit is covered.
  • Many resorted to trial-and-error clicking, backing in and out of categories, or giving up and deciding to call.
Usage data and analytics corroborated these patterns:
  • Members commonly searched using familiar terms like “MRI” or “lab work,” while the backend taxonomy only recognized formal benefit categories, creating a mismatch between how members think and how the system is organized.
  • On the Benefits & Coverage page, digital resolution was 63% and positive feedback was 58.7%, making it one of the lowest-rated digital experiences across Oscar’s products.
Problem Framing
3 Critical Pain Points
Research revealed that members were not just missing information, they were struggling to make sense of it and navigate it.
01
Unclear plan and benefits information
Members spent a lot of time trying to get a sense of their plan coverage. They landed on a dense alphabetical list of benefits with no summary of deductible status or commonly used services, leaving them unsure of where to start.
02
Complex financial context
Even when members found the right benefit, the way costs were presented made it hard to understand what they would actually pay. Coverage was framed in language such as "30% coinsurance" or "100% before deductible," without clear guidance on the underlying dollar amounts.
Because most members didn't know where they were in their plan year, they couldn't tell how much they actually owed or whether a service contributed to their deductible or out-of-pocket maximum. Members often tried to piece together meaning from past bills or assumed they would need to call to confirm, which undermined their confidence in using the digital experience as a source of truth.
03
Disconnected next steps
For members who did manage to understand their coverage and costs, the page still offered little guidance on where to get care. The benefit details page was a dead end and did not connect members to in-network care options.
Together, these problems placed a heavy cognitive burden on members at moments when they needed clarity and reassurance. The redesign needed to offload this effort to make information not just available, but intuitive, contextual, and actionable.
Ideation & Exploration
After scoring and prioritizing based on reach, impact, and level of effort, the team translated the 3 core problems into design priorities:
1
Make coverage and key benefits clear at a glance
Present key benefits, deductible status, and frequently used services on landing.
2
Help members interpret costs in context
Show where they are in their plan, explain what that means for coverage, and connect to cost estimates so they can see what they are likely to pay.
3
Guide members from coverage to care
Connect benefit details directly to in-network options.
Working closely with product and design, I explored multiple directions for each design priority. My role was to bridge members' needs with technical feasibility by surfacing plan variations, service-level constraints, and edge cases that shaped the concepts we pursued.
Across all 3 priorities, I was also responsible for translating the final designs into robust production experiences, defining accessibility behavior, responsive layouts, loading states, and error handling so the flows would be reliable across devices and plan types.
Ideation & Exploration
Make coverage and key benefits clear at a glance
The first problem we addressed was that members landed on Benefits & Coverage with no clear starting point. They saw a long list of internal benefit categories, but not a simple answer to "Where am I in my plan?"
Early explorations
In early sketches and wireframes, we tried a few different ways to help members orient on landing:
01
Option 1: Search-first
Prominent search bar, followed by a large module of top benefit categories
02
Option 2: Explanation-first
Explanation of how the plan works upfront in the benefits page, followed by a smaller module of top benefit categories
03
Option 3: Summary-first
summary of plan standing above a smaller module of top benefit categories
Usability sessions showed that the summary-first pattern helped members answer their core questions faster while still supporting those who needed to explore all benefits. We developed Option 3 further.
Introducing a Benefits Summary on landing
We introduced a Benefits Summary module at the top of the page to give members an immediate snapshot of their coverage. The module surfaces:
Current coverage status, clearly indicating whether a member:
1) has not met their deductible yet,
2) has met their deductible, or
3) met their out-of-pocket maximum
A set of commonly used benefits that we gathered from data analytics (for example, primary care, specialists, urgent care), with their typical cost share
Direct links into those benefit details if members want to go deeper
In usability sessions, members went to this summary first. Many were able to answer their core questions about where they stood in their plan year and what they would usually pay for common services without scrolling, which reduced hesitation and backtracking through the rest of the page.
Restructuring the full benefits list
To reduce reliance on formal insurance terminology, we explored plain-language labelling and top benefit tiles.
Design's first instinct for the benefits list below the summary was to rename categories in plain language so they better matched how members talk about their care. When I synced with the Benefits Service engineering team, we learned those labels came from a shared internal taxonomy used across multiple products and services. Changing them directly in the UI would require refactoring upstream data structures and risk introducing inconsistencies elsewhere in the ecosystem, which was out of scope for this project.
Bridging design intent with technical constraints, we landed on a hybrid approach:
  • Keep the canonical A–Z benefits list intact, using the existing internal taxonomy.
  • Add top benefits in plain-language tiles above the list to surface common benefits in more member-friendly terms.
  • Turn the full A–Z list into a collapsible section, so members who needed the complete taxonomy could still access it without overwhelming everyone else.
This preserved the depth and completeness while reducing the cognitive load for most members to find what they needed.
Ideation & Exploration
Help members interpret costs in context
The second problem we addressed was that members could read their coverage, but not understand what it meant financially. Terms like "100% before deductible" or "30% coinsurance" did not translate into a clear expectation of what they would actually pay.
Designing the "How Your Plan Works" explainer
To give members a clearer mental model of how their costs change over the plan year, we introduced a standalone "How Your Plan Works" explainer linked from the Benefits Summary. The explainer:
  • Shows where the member currently is in their plan journey
  • e.g. "Before meeting deductible," "After meeting deductible," "After meeting out-of-pocket maximum"
  • Explains what each phase means
  • When the member is paying the full negotiated rate versus when copays or coinsurance apply
  • Connects back to the summary, so members can see how their deductible and out-of-pocket maximum status relate to what they might pay next
This gave members a way to answer, "What does '100% before deductible' mean for me right now?" without having to reconstruct the logic from scattered coverage terms.
Connecting coverage to cost estimates
To provide more guidance on what these percentages mean for real services, we also connected coinsurance amounts on the Benefits Summary to Oscar's cost estimator. Directly from the benefits summary module, members can now jump into cost estimates for common services like primary care or specialist visits, using their actual plan and location.
This work helped turn coverage terms from abstract insurance language into a clearer picture of what members were likely to pay, grounded in where they actually were in their plan. Members no longer need to mentally translate "phase + percentage" into a rough cost on their own.
Ideation & Exploration
Guide members from understanding to action
Research showed that even when members understood their coverage, they often didn't know what to do next. Benefits & Coverage functioned as a static information page instead of a bridge into care.
Early explorations
We explored a few different ways to connect coverage to action:
  • Generic links to provider, facility, and procedure search embedded in benefit details that simply opened a search bar. These created an action, but still left members to figure out which options were relevant.
  • Specific in-network care options mapped to each benefit, such as "Find primary care providers near you" or "See in-network imaging centers," tailored to the benefit they were viewing.
Usability feedback showed that members were more likely to act when the next step was specific to the benefit they had just read about, rather than a generic "go search" entry point. Even though this meant manually curating mappings from each benefit to care options, we chose this direction because it turned coverage from static information into concrete, low-effort starting points for getting care.
Connecting coverage to in-network care and tools
We repositioned Benefits & Coverage as a decision hub by embedding next steps directly into the flow:
  • Within relevant benefit details, members can now find specific in-network providers and facilities for that service.
  • From the benefits page, members can access cost estimates and plan documents through clear entry points tied to their coverage.
  • For prescription-related benefits, members have clearer paths into pharmacy tools and medication management, rather than seeing drug coverage in isolation.
This closed the earlier gap where members could understand their coverage but still did not know how to act on it. The experience shifted from “I understand my coverage, now I have to figure out what to do” to “I understand my coverage, and I know how to take the next step.”
In testing, members followed these pathways without hesitation, confirming Benefits & Coverage as a clearer, more intuitive starting point for taking the next step in care.
Prioritization & Trade-offs
Adapting plan journey for different plan types
A major challenge surfaced early in the design phase when I raised plan variability, including:
  • $0 deductible plans that never enter a "before deductible" state
  • RX-only deductible plans that have a separate pharmacy deductible and a $0 medical deductible
  • Aggregate family accumulators that behave differently from individual accumulators
These variations meant that not all members follow the same insurance journey. Our initial designs assumed a single flow of deductible → cost sharing → out-of-pocket max, but this broke for large segments of members. For these groups, showing irrelevant phases in either the Benefits Summary or How Your Plan Works introduced confusion and risked undermining the clarity we were trying to build.
Working with design, I mapped out three paths forward for how we modeled and displayed plan phases across both components:
Option A: Maintain a single journey for all members
Irrelevant phases may display for specific plan types.
For $0 deductible plan types that don't have a "before deductible" state, this can be a confusing experience.
[member impact]
medium: shows irrelevant phases; risks confusion for members
[technical feasibility]
high: minimal engineering changes needed
[strategic fit]
medium: acceptable short-term step; enables faster delivery
Option B: Dynamically re-map the journey per plan type
Irrelevant phases are removed, preventing any confusion.
For $0 deductible plan types, "Before deductible" phase is removed.
For plan types with separate RX deductibles, deductible status will change when user clicks on the Prescription tab.
[member impact]
high: most accurate; significantly reduces cognitive load
[technical feasibility]
medium: requires dynamic logic across plan variations
[strategic fit]
high: best long-term solution for clarity, scalability, and member trust
We ultimately chose Option B. Although it required more engineering effort, it impacted all newly added features, ensured accuracy, and delivered high impact—186K+ members are on plans that did not follow the typical health insurance journey.
Raising these constraints early helped us avoid confusing states and ensured the components would remain stable as we move toward more personalized, dynamic configurations over time.
Final Experience
A decision hub for benefits and coverage
01
Make coverage and key benefits clear at a glance
before
Members landed on a long A–Z list of internal benefit categories with no summary of plan status.
after
A Benefits Summary surfaces deductible / OOPM status and common benefits on landing, with tiles + a collapsible A–Z list for deeper exploration.
02
Help members interpret costs in context
before
Coverage terms like “30% coinsurance” and "no deductible necessary" appeared in isolation, with no sense of where members were in their plan journey or what they might pay.
after
A “How Your Plan Works” explainer shows the member’s current phase in the plan and what it means, and the Benefits Summary links coinsurance entries for common services to the cost estimator so members can see likely dollar ranges.
03
Guide members from understanding to action
before
Benefit details were a dead end; members had to find provider search, cost tools, or documents elsewhere in the product.
after
Benefit details now include contextual links to find in-network providers and facilities.
Impact & Reflection
Comprehension, Confidence, and Self-Service
Over a two-month A/B test, the redesigned Benefits & Coverage experience showed clear gains:
35.9%
Increase in digital resolution
More members found the answers they needed without calling support, leading to a meaningful drop in inquiries about deductible and coverage.
The new structure and clarity directly reduced friction and increased self-service.
29.8%
Increase in positive feedback
Members reported higher satisfaction with clarity, usability, and confidence in understanding their plan, reflecting improvements in both actual and perceived comprehension.
38.8%
Increase in search engagement
Members interacted less with the benefits search bar (-11.4%). Instead, they engaged with top-searched benefit tiles, indicating that these tiles better align with their mental model.
Beyond the metrics, members described the new experience as clearer, more approachable, and "easier than calling," signaling a real shift in digital accessibility and in their ability to navigate healthcare with confidence.
What I learned
Simplifying Benefits deepened my understanding of what it takes to create clarity in a system as complex as health insurance. Even with a strong focus on APIs, plan logic, and data accuracy, it became clear that the real challenge was not exposing more information, but helping members feel confident in the decisions they were making about care.
The project reinforced a pattern I have seen across healthcare: usability is inseparable from trust and access. When people cannot interpret deductibles, accumulators, or cost sharing, the impact is not just confusion; it is hesitation, delayed care, and avoidable stress. Making insurance understandable is not an aesthetic improvement, it is non-negotiable for equitable access for people with different ages, backgrounds, and levels of health literacy.
It also showed me how tightly engineering and design shape one another. Decisions about accumulator logic, plan variations, and shared taxonomies became design decisions as much as technical ones. By turning these technical constraints into design inputs, I helped the team build an experience that guides members from understanding their coverage to taking action. The project reinforced my focus on using technical rigor to make complex systems clearer and more accessible.