Day One
A guided benefits enrollment feature that helps first-time enrollees understand their options and choose a health plan with confidence.
View Prototype
Year
2026
Platform
Mobile
Role
UX Designer
The Problem
Open enrollment uses terms like deductible and premium without explaining them.
Many people choose a plan and hope for the best.
Confusing Insurance Terms
Insurance terms like deductible and out-of-pocket max are never explained, so people guess what they mean.
Left to Figure It Out
The enrollment website lists plans and prices but doesn't help people choose one. Most turn to a parent, partner, or coworker.
Hidden Charges
Some people missed a default setting during enrollment and only found out when an extra charge showed up on their first paycheck.
The Solution
Jargon Decoded
Words that need explaining are underlined. Each one opens a simple definition with a real example.
Your Best Fit Explained
A few simple questions lead to a suggested plan and the reason behind it.
Hidden Perks Uncovered
Day One points out benefits people already pay for but rarely use, like free checkups and chiropractic care.
Payday Without Surprises
Before submitting, Day One flags anything that adds a charge, like a tobacco surcharge. Nothing unexpected shows up on a paycheck.
Background
In the US, most people pick their health insurance through work during a short window called open enrollment. Terms like deductible and premium show up with no explanation. Many people feel embarrassed to ask, so they guess.
Day One is a concept feature I designed for Fidelity NetBenefits, where millions of employees manage their workplace benefits. It's built for millennial and Gen Z employees, especially those enrolling for the first time. I handled the research, design, and testing on my own.
One person I interviewed put it this way:
"Half the words on the benefits enrollment website did not make sense to even me."
Interview participant – healthcare data professional
Research
I wanted to know why enrollment felt so hard. I looked at the tools already out there, then talked to people who had recently enrolled.
Competitive Analysis
I compared 4 benefits tools: ALEX, Nayya, Healthee, and PERKY.
•
What They Miss: Almost all of them focus on yearly open enrollment. Few help new hires, who have to choose benefits while still settling into a new job.
•
Where Day One Fits: PERKY comes closest, but it's a separate tool people have to be pointed to. Day One lives inside NetBenefits, where employees already manage their 401(k) and other workplace benefits.
•
A New Name: The feature started out as "Perks." After finding PERKY, I renamed it Day One to avoid confusion.
User Interviews
•
Who I Talked To: 5 millennial and Gen Z employees, from a first-time enrollee to someone who had enrolled many times.
•
How I Sorted It: I grouped around 80 observations into an affinity map.
What I Found
•
Confusing Language: People didn't know what basic insurance terms meant, so they made decisions before they understood them.
•
No Guidance: The platform showed plans and costs but didn't help people choose. Most people turned to a parent, partner, or coworker. Those who asked HR only got general answers.
•
Hidden Benefits: Many people were paying for coverage they didn't know they had, like massage visits or mental health support.
•
Surprise Charges: 2 people got unexpected charges on their first paycheck. One was billed a smoking surcharge because the platform marked her as a smoker by default.
Define
I turned my interviews into 3 personas. Two were enrolling on their own for the first time and one had done it for years. All three needed plain language and guidance that fit their situation. Day One had to work for all of them.
How Might We…
Ideation
I designed Day One mobile first, since millennials and Gen Z do most things on their phones. Three ideas guided every screen:
✓
Each screen asks one question
✓
Definitions appear only when someone taps a word
✓
The tone sounds like a helpful friend, not a form
I sorted my feature ideas into four groups based on my research:
•
Must-Have: Simple language definitions, a real cost estimate, warnings about default settings, and a guided flow.
•
Nice to Have: A hidden benefits spotlight, side-by-side plan comparison, and a recap card at the end.
•
Surprising and Delightful: A returning user mode and a life event detector.
•
Can Come Later: Partner/spouse coordination and a pharmacy connection.
I organized every screen into a sitemap before deciding how people would move through them. The glossary sits on its own so definitions can open from any step.
First-timers walk through every step and returning users can choose a quick update instead. Both paths include a check of default settings before submitting.
Before adding any visual design, I sketched each step in low-fidelity wireframes.
Design
First-timers needed help at almost every step. Experienced enrollees wanted to move quickly. I designed each feature to help without holding anyone back:
•
Tap to Define: The prototype defines 18 terms, from premium to qualifying life event. Experienced enrollees can skip right past them.
•
Recommend, Then Let Them Choose: Day One suggests one plan based on the person's answers and explains why. All 3 plans are still there to compare side by side.
•
Defaults in One Place: Settings that add a charge show up on one review screen before submitting. First-timers learn what they mean and returning users can confirm them quickly.
•
Benefits at the Right Moment: Benefits people often miss show up while they're looking at a plan, not after they enroll.
•
Matching Their Look: I used Fidelity's existing brand style so Day One blends in with the rest of the site.
•
A Friendly Voice: People turned to friends and family for help, so Day One talks like one. It uses everyday words, explains why it asks each question, and reminds people that nothing is final until they submit.
Testing & Iterations
I tested Day One twice with 5 people each, mixing first-time and experienced enrollees. Round 1 used mid-fidelity wireframes and round 2 used a high-fidelity prototype. Each person went through the full flow:
•
Starting enrollment and answering the questions
•
Reading what a plan costs and looking up a term
•
Comparing plans and submitting
•
Feedback: In round 1, Day One asked if people wanted a health savings account (HSA) before they picked a plan. HSAs only come with certain plans, so they couldn't answer yet.
•
Final Iteration: I moved the question to after they choose a plan, when the answer is clear.
Earlier Version
Final Version
•
Feedback: Day One first showed each plan's yearly cost. Testers saw numbers like $6,500 and worried before they understood them. Several said they'd rather see the paycheck amount first, since that's what affects their budget.
•
Final Iteration: Cost screens now lead with the per paycheck amount. The full-year estimate moved to each plan's details page, one tap away.
Earlier Version
Final Version
•
Feedback: Several people asked how Day One knew they would hit their deductible. The screen never said, so they had no reason to trust the suggestion.
•
Final Iteration: Each reason now points back to their own answers, like "Based on the visits and prescriptions you expect, you'll probably meet your $750 deductible."
Earlier Version
Final Version
•
Feedback: People liked the hidden benefits section, but few noticed it on their own. Most testers also didn't know an HSA could pay for everyday things like sunscreen or chiropractic visits.
•
Final Iteration: The hidden benefits got their own card so they stand out. The HSA screen now lists real examples instead of just a definition.
Earlier Version
Final Version
Results
In the final round, testers made it through the full enrollment flow without hitting a dead end. Most of what I changed was about trust. People needed to understand the costs and believe the plan Day One suggested.
•
For First-Timers: Every suggestion comes with a reason based on their own answers, so they can trust it.
•
For Experienced Enrollees: A quick update path lets them review their defaults and submit without redoing every step.
•
For Fidelity: A few testers said the HSA examples alone would make them sign up. That means more use of the accounts Fidelity offers.
Final Prototype
Final Thoughts
Day One taught me that clear information isn't enough. What users cared about most was how a plan would affect their paycheck and fit their current situation. Generic plan details didn't help them choose. It also taught me that good content can still fail if it's hard to find. Every tester was excited about the hidden benefits section once they saw it, but at first few could find it on their own. That isn't something I would have caught by myself. Watching real people use the design is what showed me. It's the reason testing will always be a core part of my process.
Next Steps
•
Is My Doctor Covered?: Let people see whether their current doctor is in each plan's network. Testers brought this up without being asked in several sessions.
•
Start With What Matters: Ask people early what they care about, like eye care or seeing a chiropractor. Day One could then show how an HSA could pay for those exact things.
•
Plan for Life Events: Add a path for moments like turning 26, when people leave a parent's plan and pick their own coverage for the first time. Starting a job mid-year or expecting a baby would fit here too.
•
Measure Understanding: Ask people to rate their confidence from 1 to 5 before and after using Day One. A few quick questions could also check what they learned.
What I'm Most Proud Of: Turning one of the most confusing decisions of the year into something people don't have to dread. Day One explains each step, shows costs in paycheck terms, and stays with people until they submit. I'm also proud that it works for first-timers and experienced enrollees without slowing either one down. Whether it's someone's first time or their tenth, Day One meets them where they are.