How We Got Stuck

For years the pattern repeated. Designers would sketch a better version. Leadership would nod. Then the conversation would hit the same wall: you couldn’t meaningfully redesign the experience without upgrading the underlying platform at the same time. A cosmetic facelift on the old stack would be throw-away work. A full platform migration was a heavy, expensive lift that never quite justified itself when measured against any single product’s roadmap.

So the page sat. Year after year.

What Changed

Early in the year I did something small. I brainstormed a concept with the team using our modern design system and started quietly showing it around. No formal project. Just a prototype. One of the people who saw it was a marketing VP who immediately got excited. Around the same time, another team had already stood up a solid modern platform for a different product line. Suddenly the biggest technical barrier had been removed for us.

Funding followed—pieced together from two business units that saw the shared value. We kicked off with a tightly scoped MVP, heavy research, and a clear rule: start from the member’s actual reason for logging in, not from our internal data model.

We treated the page like a theater lobby. No one goes to the movies to hang out in the lobby, but the lobby still has to get you efficiently into the right theater while offering a few useful side options along the way. That metaphor kept us honest.

Designing, Testing, and Listening

We pivoted hard away from the old “link farm” approach. The new design reconfigures based on what coverages and account information the member actually has. We ran card sorts, tree tests, and multiple rounds of moderated usability testing—seven iterations and more than 350 participants between desktop and mobile.

One finding still makes me smile. We assumed “Start a claim or request” was a clear label. Early success rates sat around 30%. We rewrote the test prompt. Still low. We rewrote the supporting text. Better, but not great. The thing that finally pushed task success above 70% was a tiny word-order change: “Start a request or claim.”

Sometimes the smallest language tweak is the difference between confusion and confidence.

Overall, the tested designs improved task completion between 6% and 73% and cut time-on-task on every scenario we measured. The lighter UX metrics we track also moved in the right direction. Those numbers mattered. They gave us the confidence to lock the design and move into development.

What We Learned (Again)

A few lessons kept surfacing:

• Experience designers should protect the shared spaces. If no one owns the commons, it decays. We can—and should—propose the work.
• Start with the member’s actual journey and intent, not the internal system diagram.
• Research early and often is the best defense against “protecting my turf” arguments and pure anecdata.
• Measurement is not optional. The results we can show will determine whether we get to keep improving these shared experiences next year.
• Never stop chasing the whale. You never know when the conditions will finally align.

The page is in development now and expected to reach pilot members soon. I’m cautiously optimistic. More importantly, I’m reminded why this work still matters.

The white whale was never really the page. It was the quiet acceptance that some experiences are just “how we’ve always done it.” Once you stop accepting that, the hunt becomes possible again.

Call me Ishmael. I’m still sailing.