Day One
Day One is a guided benefits enrollment feature that helps first time enrollees understand their options and choose a health plan with confidence.
Role
UX Designer
Industry
Health Benefits
Service
UX Design
Year
2026
Tools
Figma, FigJam
Methods
Competitor analysis, interviews, affinity mapping, usability testing
Overview
Day One is a guided benefits enrollment feature I designed during my Designlab UX Academy program. It lives inside Fidelity NetBenefits, the platform millions of employees use to manage their workplace benefits. It is built for millennial and Gen Z employees enrolling for the first time. I handled the research, design and testing on my own. Since this was a feature for an existing product, every design decision stayed true to Fidelity's brand.
The Challenge
Open enrollment is one of the most stressful financial decisions people make each year. Terms like deductible, premium and in network show up with no explanation. Many people feel embarrassed to ask what seem like basic questions, so they guess. They pick the cheapest plan, copy what they had before, or skip sections entirely. More than half of Americans end up regretting their benefits choices.
This matters for Fidelity too. When people guess or skip sections, they miss out on health savings and flexible spending accounts, which let people set aside money before taxes for medical costs. Fidelity offers both. Fidelity also misses the chance to build trust with younger users at one of the biggest financial moments of their year.
Research & User Insights
I started by looking at 4 benefits tools: ALEX, Nayya, Healthee and PERKY. Almost none of them were built for someone starting a new job. Most focused on open enrollment for people already at the company.
I then interviewed 5 millennial and Gen Z employees at different life stages, from a first time enrollee to someone who had enrolled many times. I sorted around 80 observations into an affinity map. 4 problems came up:
• Confusing language. Terms like deductible and premium had no explanation. People felt embarrassed to ask, so they made decisions before they understood them.
• No guidance. The enrollment platform showed plan options and costs but did not help people figure out which plan fit their life. No one relied on the platform for help. Everyone turned to a parent, partner or coworker instead.
• Hidden benefits. Many people did not know their plan already covered things like chiropractic visits or mental health support.
• Surprise charges. 2 people got unexpected charges on their first paycheck. For example, one person was billed a smoking surcharge because the platform marked her as a smoker by default. She did not know this when she signed up and only found out when a coworker brought it up.
User Needs
• Plain explanations of benefits terms without having to ask
• Guidance on which plan fits their life
• A clear view of the benefits they already have
• No surprise charges after they enroll
The Solution
Day One lives inside NetBenefits and walks people through enrollment one step at a time. Each part solves one of the problems from my research:
• Confusing language: People can tap any underlined word, like deductible, to see a simple definition with a real example.
• No guidance: Day One asks a few simple questions, like who will be on their plan and how often they expect to see a doctor. It then suggests the plan that fits them best and explains why.
• Hidden benefits: A "Most people miss these" card shows useful perks people are already paying for but rarely know about, like free checkups, chiropractic care and massage therapy.
• Surprise charges: Before submitting, Day One flags defaults like a tobacco surcharge so nothing shows up unexpectedly on a paycheck.
Design Approach
I designed Day One mobile first, since millennials and Gen Z do most things on their phones. I started with low fidelity wireframes to figure out the best way to show definitions and warnings. Before adding any visual design, I tested mid fidelity wireframes with 5 people. The hardest part was that Day One had to work for both first timers and people who enroll every year. What felt clear to one group felt confusing or too basic to the other. 3 things guided every screen:
• Each screen asks one question at a time. People in my interviews described enrollment as overwhelming, so I kept every step small.
• Definitions stay hidden until someone taps an underlined word. First timers get help when they need it and experienced users are not slowed down.
• The tone feels like a knowledgeable friend instead of a form. People in my interviews turned to friends and family for help, so Day One speaks the way a helpful friend would.
I built on Fidelity's existing brand style so Day One feels like a natural part of NetBenefits.
Testing & Iteration
I tested a clickable prototype with 5 people. Some were enrolling for the first time and others had enrolled before but still found it confusing. Each session lasted about 30 minutes, either remote or in person. People worked through 6 tasks, from opening Day One to submitting their enrollment.
Every person made it through the full flow without getting stuck, which told me the overall structure worked. Most problems came from how costs were shown, whether people trusted the plan Day One suggested and whether they noticed helpful information like hidden benefits. Here is what I changed:
• People read the name Day One as onboarding, not benefits. A few asked what it was for before leaving the home screen. I added a short tagline under the name: "Benefits Enrollment, one easy step at a time."
• Day One first showed the yearly cost of each plan. People reacted to these large numbers before they understood what they meant. They told me they think about money by paycheck, not by year. Every cost screen now shows the per paycheck amount first, with the yearly total underneath.
• Several people asked how Day One chose the plan it suggested. Without a reason, they had no way to know if it fit. The suggestion screen now explains why, using their own answers, like how many doctor visits they expect.
• People found the "Most people miss these" section useful, but few noticed it on their own because it blended in. I gave it its own card so it stands out.
• People had no idea their health savings account (HSA) could pay for everyday things like glasses or sunscreen. An HSA lets people set aside money before taxes for medical costs. When we talked through examples, some said that alone would make them set one up. The HSA screen now lists real examples instead of just a definition.
• In the prototype, the person's workplace offers 3 health plans. Day One suggests the one that fits best, and people can then compare all 3 side by side. But the compare screen did not show which plan Day One had just suggested, so the suggestion screen and the compare screen felt disconnected. Now the suggested plan is already selected when people open the compare screen. They can still switch to a different plan if they want.
Learning & Next Steps
The biggest lesson from Day One was that definitions alone don't help people decide. Real examples tied to their money and health do. I also learned that a helpful feature only works if people notice it. The "Most people miss these" section is a good example. People loved it once they saw it, but few found it on their own. Now I think about how easy something is to find from the start, not as a last step. Testing also showed me that people don't always use a design the way I expect. So I base my changes on what I see in testing, not on my assumptions.
Next steps:
• Test a simple way for people to check if their current doctor is covered by each plan. Several people asked for this on their own.
• Ask people early on what they care about, like eye care or seeing a chiropractor. Day One could then show how a health savings account could pay for those exact things. Several testers suggested this.