Day One
Helping first-time enrollees choose a health plan they actually understand
In the US, most people pick their health insurance through work during a short window called open enrollment. For someone doing it for the first time, that means a wall of terms like deductible and premium, with nobody explaining them.
In 5 interviews, not one person relied on the enrollment platform for help. Everyone turned to a parent, partner or coworker instead. One participant works with healthcare data for a living and still said half the words didn't make sense to her. Two people were hit with surprise charges on their first paycheck.
As the sole designer, I created Day One, a guided enrollment feature inside Fidelity NetBenefits. It asks a few simple questions, suggests a plan and explains why. I tested it in 2 rounds with 5 people each. In the final round, every participant finished enrollment without getting stuck.
Role
UX Designer
Context
Designlab UX Academy
Industry
Health Benefits
Year
2026
Tools
Figma, FigJam
Methods
Competitor analysis, 5 interviews, affinity map, personas, 2 rounds of usability testing
Most people don't understand their health plan
Only 14% of insured Americans could correctly explain all 4 basics of their plan: deductible, copay, coinsurance and out-of-pocket maximum (Journal of Health Economics, 2013). 53% of Americans with workplace benefits regretted their choices from their last open enrollment (Equitable, 2024).
Younger workers have it hardest. People ages 18 to 43 were twice as likely as older generations to pick a plan blindly, and 29% said they would rather do their taxes (Harris Poll for Justworks, 2024).
The help people needed came from people, not the platform
I interviewed 5 millennial and Gen Z employees, from a first-time enrollee to someone who had enrolled many times. I sorted around 80 observations into an affinity map and built personas from what I heard:
• Melanie, the first-timer: "I just remember not knowing what any of the words meant."
• Angelica, who aged off her parents' plan at 26: "Half the words on the benefits enrollment website did not make sense to me."
• Donnie, the experienced enrollee: "The most stressful thing is feeling locked into a decision you might get wrong."
• Chelsey, the family planner: "Choosing a plan you don't use is like paying for a credit card and never using the rewards."
One participant remembered a guided tool his employer used years ago. It explained everything in plain language and even added a little humor. His employer later replaced it with a standard platform. It was the closest thing to Day One anyone had used.
The gap other tools left open
I looked at 4 benefits tools: ALEX, Nayya, Healthee and PERKY. Almost all of them focus on yearly open enrollment, not the moment someone starts a new job. The closest one, PERKY, is a separate tool people have to be sent to. Day One lives inside NetBenefits, where employees already go.
The feature started out as "Perks." After finding PERKY, a competitor with a similar name, I renamed it Day One to avoid confusion.
4 decisions that shaped Day One
1. Define terms only when someone asks. I worried that defining every term would teach people to ignore the definitions. So underlined words open a short definition only when tapped. The prototype covers 18 terms, from premium to qualifying life event.
2. Suggest a plan but leave the choice to them. Going into testing, my biggest question was whether a suggestion would feel like help or like steering. Day One suggests one plan, explains why using the person's own answers and still shows all 3 plans side by side.
3. Only ask what people can answer. In round 1, Day One asked about health savings accounts before people knew whether their plan qualified for one. I moved that question to after they choose a plan.
4. Catch surprises before they submit. A "Before you submit" screen flags defaults like the tobacco surcharge, so nothing new shows up on a paycheck.
Underlined words open a short definition
Day One checks your answers before it suggests a plan
Defaults like the tobacco surcharge get flagged
Round 1 fixed the flow. Round 2 was about trust.
Round 1 used wireframes with 3 newer and 2 experienced enrollees. It fixed the question order, added a clear way to pick a plan on the compare screen, split out the confusing "worst case" cost and added tap-to-define.
Round 2 used the high fidelity prototype with 5 people:
• A yearly cost of $6,500 alarmed people before they understood it. Every cost screen now leads with the per paycheck amount.
• People asked why Day One chose their plan. It now says something like "Based on the visits you expect, you'll probably meet your $750 deductible."
• Few people noticed "Most people miss these," so it got its own card.
• People didn't know what a health savings account (HSA) could pay for. When we talked through real examples, some said that alone would make them sign up.
• The compare screen now starts on the suggested plan.
• People read "Day One" as onboarding, so I added a tagline.
I also flagged risks: the wording of the plan priority options might sway people toward one choice, and terms like spouse, partner and kids weren't used consistently.
Before: the yearly cost came first
After: the per paycheck cost comes first
Before: general reasons and a plain hidden benefits section
After: reasons based on their answers and a card that stands out
Before: only a definition
After: real things an HSA pays for
Before: a different plan was selected
After: the suggested plan is selected
What I learned and what's next
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. People loved "Most people miss these" 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.
Some requests were out of scope, but people brought them up on their own in both rounds: checking whether their doctor is covered, plus vision, dental and medication coverage.
Next, I would:
• Test a simple way to check whether your doctor is covered, before building a full provider search
• Ask people early what matters to them, like eye care, and show how an HSA could pay for those things
• Add a path for life events like turning 26 or starting a job mid-year
• Measure understanding with a short quiz and a 1 to 5 confidence rating at the start and end of each session
• Test 2 versions of the suggestion wording to check whether it steers people
• Talk with HR and benefits staff, since people avoided asking them questions that felt too basic