Fewer than one in four people who started buying a policy online actually finished. The easy answer was “the site is clunky.” It wasn’t. I found what was really happening, redesigned around it, and the beta cut drop-off roughly in half.
The unified self-service dashboard — one place to see coverage, family, and certificates.
They were the reassurance. That was the product, as much as the policy.
When someone buys health insurance, they’re scared of getting it wrong. Pick the wrong plan and your family isn’t covered when it matters. Miss a field and your premium is off. The human agent absorbed all of that fear — reassuring people, catching mistakes before they happened, quietly signalling “you’re doing this right.”
When the company moved the journey online, it moved the forms but not the reassurance. So people did exactly what you’d expect: they started, got anxious, and called support for the hand-holding they used to get in person. The website wasn’t failing because it was ugly. It was failing because it left people alone with a high-stakes decision.
Research made the pattern impossible to miss. Stakeholder interviews across product, ops, legal, sales and the call center. Live purchase and support calls. Usability tests on the legacy flow. A deep dig through drop-off analytics. Three findings did the heavy lifting.
Over 60% of drop-offs happened at exactly two steps: adding a family member, and uploading documents — the precise points where stakes felt highest and guidance was thinnest.
They didn’t need fourteen plan variants. They needed to know the choice in front of them actually covered their family. Progress and safety cues beat feature breadth.
Customers dreaded requesting a certificate because they had no idea when it would arrive. Instant, visible issuance turned out to be the single biggest unlock.
The Family Decision-Maker (35–50, mid-income) wants reliable coverage for their dependents, fast, and is terrified of missing something. The Policy Administrator is an existing member who just wants to manage changes without phoning support.
Design implication: transparency and safety nets aren’t nice-to-haves. They are the feature.
Personalized recommendations and side-by-side comparison, with progressive disclosure so people aren’t drowning in options. The rest stays out of the way until needed.
The worst drop-off point got the most care. A step-by-step wizard with auto-validation on age and relationship, plus a live premium preview as each person is added.
An online form generates a downloadable PDF on the spot, with status tracking in the dashboard. The 3–5 day wait and the branch visit both disappeared.
One place to track applications, view policies and manage changes — with notifications and quick actions for renew, update and cancel.
Every component existed to rebuild reassurance. Progress indicators so people always know where they are. Confidence badges and “you’re covered if…” language at decision points. Action confirmations so nothing feels irreversible. Status cards so waiting never feels like a black box.
| Before | After |
|---|---|
| Multi-session slog | Single guided session |
| Offline uploads and delays | Real-time validation and previews |
| No unified view | One order dashboard |
| Constant support dependency | Self-service certificate download |
Numbers I stand behind
Real, but softer — depends on sustained behavior
My job wasn’t to choose between user trust and legal risk. It was to find the design that served both.
Legal and compliance wanted every disclaimer surfaced up front, before the customer committed to anything. Reasonable risk management, from their seat. But research was unambiguous: front-loading dense legal language was exactly what spooked anxious customers and sent them to the exit. The thing meant to protect the company was helping kill the conversion.
So I made a call. We kept every required disclosure, but moved it to the moment of relevance using progressive disclosure — plain-language summaries first, full legal text one tap away. I took that to compliance with the drop-off data and the user-fear evidence side by side, framed as risk reduction for both sides: fewer abandoned sessions means fewer error-ridden workarounds, which is its own compliance exposure. They signed off.
Two things. I’d test personalization harder — there was more conversion and SUS to win, and we left some on the table. And I’d bring legal into co-design earlier, in the room while we sketched. The compromise that took weeks could have been a thirty-minute whiteboard session in week two.
Role — UX Leader: strategy, research, interaction design, governance alignment
Team — Me + 3 senior product designers, 2 UX researchers, and partners across engineering, product, legal & operations
What I owned — Research strategy for sensitive health data, the end-to-end journey, the trust & adoption metrics, translating compliance constraints into usable requirements, and the executive case tying user trust to revenue.