Medicare Supplement
Enrollment Journey
Turned a fragmented, legacy enrollment process into a clear, carrier-aware guided journey — reducing cognitive load and enabling scalable, compliant digital enrollment across markets
ROLE
Lead Designer
TIMELINE
2025
SCOPE
End-to-end redesign
PLATFORM
Desktop
Partners
Product, Engineering, Compliance, Research
01 OVERVIEW
MY CONTRIBUTION
Discovery & workflow architecture
Carrier flow analysis & synthesis
Interaction & UX design
Content strategy collaboration
Usability testing & iteration
Hi-fi prototypes & dev handoff
Compliance alignment
Tools
Figma, Miro
ChatGPT, Napkin (process diagrams)
Hotjar, Usertesting
A rigid legacy system holding back a complex, high-stakes enrollment
Medicare Supplement enrollment is one of the most consequential financial decisions a user makes — yet the existing experience was built on Castro, a legacy system that couldn't flex to carrier-specific requirements or guide users with confidence.
As Senior Product Designer, I led the end-to-end redesign: from discovery and workflow architecture through interaction design and dev handoff. The new system, built on Muse v4, adapts dynamically to each carrier's rules while delivering a consistent, human-centered experience at every step.
02 PRBLEM STATEMENT
One rigid system.
Dozens of carriers. Zero flexibility.
The legacy enrollment experience couldn't keep up with the complexity of the Medicare Supplement market.
The current enrollment experience was built on Castro — a legacy system that was difficult to navigate, rigid, and not intuitive for users. Its limited flexibility made it nearly impossible to support carrier-specific questions, resulting in a fragmented enrollment experience and increased cognitive load for users completing one of the most consequential financial forms of their lives.
Carriers like Humana, Aetna, Anthem, and UnitedHealthcare each have distinct underwriting rules, eligibility questions, and compliance requirements. Castro could not adapt — forcing users through irrelevant questions and agents into manual workarounds.
"Users were navigating a form built for the carrier's back-office, not for the person trying to enroll in coverage."
03 GOALS & SUCESS METRICS
What success looked like
01
Reduce Cognitive Load
Surface only the questions relevant to each user's carrier, plan, and eligibility status — nothing more.
02
Support Carrier-Specific Requirements
Enable a single unified flow that dynamically adapts to each carrier's underwriting and compliance rules.
03
Increase User Confidence
Help users understand what's required and why, so they move through enrollment with trust rather than anxiety.
04
Enable Scalable Compliance
Design a system architecture flexible enough to onboard new carriers without redesigning the experience each time.
04 Research & Discovery
Studying the carriers before designing the flow
Before sketching a single screen, I examined how each major carrier structured their enrollment requirements.
I examined enrollment flows across Humana, Aetna, Anthem, and UnitedHealthcare to identify shared questions and carrier-specific requirements. This informed the creation of a unified application architecture that could flex without fracturing the user experience.
Early sketches were reviewed with stakeholders and compliance partners. User testing was then conducted on those sketches to validate the flow structure before moving into hi-fi design.
05 Insights & Problem Framing
What the research revealed
01
Complexity is real — but most of it is invisible to users
Carrier-specific rules (guaranteed issue, underwriting, household discounts) are genuinely complex, but users don't need to understand the rules — they just need to be guided through their slice of them.
02
Irrelevant questions erode trust
When users encounter questions that don't apply to their situation, they lose confidence in the process and become more likely to abandon or call an agent for help.
03
High-stakes forms need visible guidance
In a regulated enrollment context, hiding help text increases anxiety. Users need to see why a question is being asked, especially around health and eligibility.
04
Agents needed a flow they could trust too
Agents were compensating for the old system's rigidity with manual workarounds. A cleaner flow would benefit users and agents equally.
How Might We: "How might we build a single enrollment experience that feels simple and personal — even when the underlying carrier requirements are radically different?"
How Might We: "How might we build a single enrollment experience that feels simple and personal — even when the underlying carrier requirements are radically different?"
06 DESIGN PRINCIPALS
Four principles that guided every decision.
Principle 01
Clarity over complexity
Break down regulatory and underwriting requirements into clear, understandable steps. No legal speak. No surprises
Principle 02
Progressive disclosure
Surface health, eligibility, and additional questions only when required — reducing cognitive load at each step.
Principle 03
Consistency with flexibility
Standardize the experience across carriers while adapting dynamically to carrier-specific rules under the hood.
Principle 04
Confidence through transperance
Clearly communicate what's required and why — helping users move forward with trust rather than uncertainty.
07 USER FLOW & INFORMATIONAL ARCHITECTURE
One flow. Every carrier.
I synthesized enrollment requirements across multiple carriers into a single unified application architecture that branches intelligently based on eligibility and carrier rules.
The key architectural decision was the guaranteed issue branch. If a user is in their guaranteed issue period, health underwriting questions are bypassed entirely — reducing the form significantly and removing unnecessary anxiety. If underwriting is required, health history and health questions are surfaced progressively, only after the user understands why.
The result: a single flow that handles Applicant Information → Coverage → Eligibility → (conditional: Health History + Health Questions) → Additional → Payment → Summary — for every carrier, without fracturing the experience.
08 DESIGN PROCESS
A lifecycle built for regulated complexity
Medicare Supplement enrollment isn't just a UX problem — it's a compliance problem. The design process had to accommodate carrier stakeholders, legal review cycles, and underwriting rules alongside standard UX iteration loops. I structured the work as an interconnected lifecycle rather than a linear waterfall: discovery and compliance alignment ran in parallel, and stakeholder reviews were embedded throughout rather than saved for the end.
Product Development Lifecycle
09 CONTENT STRATEGY
Copy that guides, not intimidates
Collaborated with content design and research to develop and test clear, user-centered copy for a regulated enrollment experience.
Four content principles
Clear, Friendly, Human: Plain language throughout. Each section explains what's needed and why — no legal speak, no surprises.
Consistency Builds Confidence: Clear titles, predictable structure, and supportive copy reduce cognitive load and keep users moving.
Educate, Don't Hide: All guidance is visible by default. In a high-stakes flow, hiding information increases uncertainty. Keeping copy visible ensures users feel informed and avoid mistakes.
Progressive, Not Overwhelming: Information is concise, scannable, and broken into manageable steps — supporting steady progress without overload.
10 WIREFRAMES & ITERATION
Sketching early, validating often
Early sketches were created to review with stakeholders and compliance partners before any visual design began. These were low-fidelity enough to invite feedback, but structured enough to represent real flow decisions. User testing on these sketches validated the step structure and revealed where guidance copy was most critical.
11 FINALE SOLUTION
A guided journey that adapts to every carrier
The redesigned enrollment experience on Muse v4 — clear, progressive, and carrier-aware.
Key design decisions.
Stepper navigation: A persistent left-rail stepper gives users a clear sense of progress and orientation across all sections — Applicant Information, Enrollment Status, Health Evaluation, Payment, Additional Information, Summary.
Contextual plan summary: The user's selected plan and key benefits are shown inline during enrollment, reducing back-and-forth and supporting informed decision-making.
Progressive disclosure of health questions: Health evaluation sections are surfaced only when the user's eligibility status requires underwriting — with clear explanation of why before the questions appear.
Carrier-aware content: Carrier-specific requirements are handled in the backend configuration, not the UI — keeping the experience consistent for users regardless of which carrier they're enrolling with.
11 TESTING & VALIDATION
Tested early. Iterated continuously.
User testing was conducted across multiple rounds — starting with sketches, continuing through mid-fidelity wireframes, and concluding with hi-fi prototypes. Testing focused on three areas: step comprehension (do users understand what's being asked and why?), flow navigation (do users know where they are and what comes next?), and copy clarity (does the language build or erode confidence?).