Product designer at Obie — insurance software, and the way it gets built
I asked that all year. This is the answer I built: a handoff that runs.
The policy page prototype, one page for three audiences. Fictional data.
This prototype ran on 24 fictional policies for 10 weeks. Engineering wrote the spec from it, and the first production pull request shipped all nine of its tabs behind a flag. The code was rebuilt; the decisions carried over.
When Obie opened its platform to independent agents, the page they’d live in was built for our own brokers. I redesigned what it was organized around. Three years later, it’s one of the most-used pages in the product.
The page everyone opened and nobody could read. Six decisions so an agent can answer three questions before they scroll.
The status pill becomes a sentence: what happened, when, and what to do next.
Status, balance, due date and the one action that matters, in a single card.
On a healthy policy the page goes quiet. No alert, nothing to act on.
Pick a term and every value above the tabs follows it.
Nine tabs. Policy History is one timeline across every term, not just the one you’re on.
The new page arrives as an invitation from the old one, not a forced switch.
After the acquisition, an entirely new line of business in four months, launched in April 2026.
After launch, sessions hitting an error fell from about 30% to about 6%.
Agents see their job as building a quote, the document they send their client. So I designed customization like a product configurator, the way you build a car or spec a laptop: choices in the workspace, the quote beside them. The first release made the quote PDF available during customization, with coverage cards that mirror it line for line.
Agents have called it the smartest quoting interface they’ve seen.
Agency onboarding and an agent-portal sprint: what changed when product, design and engineering started together, including the big build we chose not to start.
How AI prototyping went from a few people working alone to the way all three of our PMs, design and engineering decide what to build. Three projects so far: agency onboarding, the policy page, and the underwriting workbench.
Where the hard decision landed
Core interaction re-decided, after the build began
Structure, banners and billing decided inside the prototype, before any spec
How design came to set the terms for how work moves from idea to production at Obie, and why that had to change before anything else could.
An agent building a quote. A policyholder checking what they owe. An underwriter deciding on a risk. And an engineer, opening whatever I hand them. Designing for that last one is why our handoff became working software.