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. We:
- 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.
Design Priority 1
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, and what do I usually use?"
Early explorations
In early sketches and wireframes, we tried a few different ways to help members orient on landing:
- Search-first layout with a prominent search bar, followed by a module of common benefit categories
- Overview-heavy page that explained how the plan worked in a scrollable narrative
- A compact summary on top of a refined list, which balanced a quick snapshot with access to the full set of benefits
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, so we developed this direction 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.
Design Priority 2
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.
Early explorations
We brainstormed several approaches to make costs feel more concrete:
Inline dollar examples with estimated costs for each benefit (for example, "A typical visit costs around $X–Y").
These made costs feel real, but were difficult to keep accurate across markets and plan years.
A "How insurance works" block at the top of the page explaining complex insurance terms and plan journey.
Members often skimmed or skipped it and struggled to connect the definitions back to their own situation.
Rich tooltips on coverage terms such as "deductible", "coinsurance", and "allowed amount."
These helped locally, but did not give a holistic picture of how costs changed over the year.
A plan journey view that showed where the member was in their plan and what each phase meant for their costs.
Concept reviews and early usability feedback showed that the journey-based view was most promising, especially when paired with ways to see actual dollar ranges. We developed this direction further.
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
- For example, "Before deductible," "After deductible," or "Out-of-pocket maximum reached"
- Explains what that phase means in plain language
- 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.
Design Priority 3
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 the 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:
A) Hide the summary table
Show only a high-level status indicator (for example, "You've met your deductible"). While very easy to implement, it made marginal improvements to our current experience. This option was eliminated quickly.
B) Maintain a single journey for all members
Preserve the current table structure by defaulting the start of plan to "after deductible" for $0 deductible members. This required less engineering effort and kept most of the experience intact, but still risked showing phases that didn't strictly apply to every plan, especially for $0 deductible plan types that didn't have a "before deductible" state.
C) Dynamically re-map the journey per plan type
Tailor phases so members only saw steps relevant to their plan (for example, remove the "before deductible" plan phase for $0 deductible plans, or adjusting the journey for RX-only configurations). This offered the highest clarity and long-term scalability, but required more complex logic across multiple plan variations.
option B: maintain 3 phase journey for all
"Before meeting deductible" is an irrelevant phase for $0 deductible plans
option C: dynamically map phases
Irrelevant phases are removed, preventing any confusion
We ultimately chose Option C. Although it required more engineering effort, it ensured accuracy across both the Benefits Summary and How Your Plan Works, reduced cognitive load, and delivered high impact, as more than 186K members were on plans that did not follow the typical health insurance journey.
As the engineering lead, I designed the underlying plan-journey logic and the Benefits Summary module as reusable, scalable components that could flex across individual plans, aggregate and embedded family accumulators, $0-deductible plans, and RX-only deductibles without breaking or showing misleading information. 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
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.
