— PROJECT NAME
Digital special enrollment for year round applications
— ROLE
UX Researcher
UX Strategist
UX Designer
Accessibility expert
— DATE
2/10/2026
*This is a current work in progress as of April 8, 2026*
The Commercial Special Enrollment process was built entirely around a paper application. No online form, no qualifying event guidance, no document upload, and no real-time feedback. As the organization moved toward year‑round enrollment, this legacy workflow became a major barrier. I stepped in to modernize the system from the ground up: mapping the complex OE/SEP overlap, clarifying regulatory rules, and designing a digital experience that replaces a static PDF with a dynamic, compliant, member-friendly application flow.
Problems and constraints
Regulatory ambiguity
The paper application listed only a subset of qualifying events, meaning the online version needs to be more complete, accurate, or point people to the information they need. Effective date rules were unclear and required cross-team collaboration and alignment.
Fragmented user flow
The paper application listed only a subset of qualifying events, meaning the online version needs to be more complete, accurate, or point people to the information they need. Effective date rules were unclear and required cross-team collaboration and alignment.
Missing digital touchpoints
No pre-shopping qualifying event selection, no document upload capabilities, and no clear ‘what happens next’ messaging.
Mapping the journey
I felt like it was important to start by mapping out the standard open enrollment flow. And then from there, being able to add the special enrollment flow. This allowed for a complete overhead look at what the process looks like.
Being able to look at the special enrollment requirements, I was able to pinpoint the decision points, and regulatory triggers that we would have to add to our digital flow.
The standard open enrollment flow for new users, current members, and agents.
The open enrollment flow, in addition to the special enrollment flow with additional requirements, and steps, with the user selecting their qualifying event before seeing the plans.
The final version of our flow shows the list of qualifying events after the user selects a plan, instead of before. This flowed seamlessly into the user filling out their enrollment application.
UX Challenges & Solutions
Challenge 1: Qualifying event selection was incomplete and confusing
- Expanded the list based on regulatory guidance and membership accounting insights
- Designed a clearer, more inclusive selection interface
- Added documentation expectations upfront to reduce drop-off and call volume
Challenge 2: Effective date rules were ambiguous
- I facilitated cross-team conversations to define what flexibility users should have
- I designed a pattern that shows the calculated effective date and explains why
- I ensured the logic was accessible and transparent
Challenge 3: No upload capabilities
- - Designed a post‑shopping upload step with clear file requirements.
- - Collaborated with dev to define file types and size limits.
- - Ensured the upload flow met accessibility standards
Challenge 4: The final confirmation page lacked guidance
- - Rewrote the messaging to set expectations about review timelines
- - Added a downloadable PDF of the completed application + attachments
- - Ensured the page worked for assistive technologies and mobile users
Our design options for initial entry
Below are the two options that were designed to get users from the entry page to their results. One options requires more work from the user, by adding four additional pages to the entry flow, as well as the overall application. The other requires more work from our engineers as it strays from our traditional entry form, and would require a shift in how we have designed for shopping in the past.
Option 1
The user must enter all information in regards to their special enrollment qualifications in order to see the plans and prices available in their area. This would come after the initial entry page where they give their name, zip code, type of coverage, and birthdate information. This would require four additional pages for the application flow, with two of those pages being informational only.
Option 2
We instead add the users qualifying event information in the entry experience. This would take additional pages out of the flow, would allow the backend to calculate their effective date and assign it to them without additional steps, and gets the user to the results faster, with less clicks.
Marketable growth
60% increase in special enrollment applications
Increased user acceptance
- 32% increase in completed applications
Improved user experience
- “This made my enrollment so much easier than filling out a PDF and having to mail it”
Greater enrollment
email@domain.com
000-000-000
Project emphasizers
- This project highlights:
- - My ability to clarify ambiguous requirements
- -My strength in visualizing complex, conditional user journeys
- - My cross‑functional collaboration with regulatory, membership accounting, and dev teams
- - My accessibility and UX rigor in high‑stakes, compliance‑driven environments