Breaking the Handoff
What happened when a product team stopped passing work down an assembly line, and the big build we deliberately didn’t start.
Product designer at Obie — insurance software, and the way it gets built
If I’ve already built it in working code,
why am I handing engineering
a picture of it?
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.
The handoff stopped being a file
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
Quote builder, 2025shipped week 30
Core interaction re-decided, after the build began
Policy page, 2026final design built week 10
Structure, banners and billing decided inside the prototype, before any spec
The policy page
The page everyone opened and nobody could read. Six decisions so an agent can answer three questions before they scroll.
One banner, and it tells the truth
The status pill becomes a sentence: what happened, when, and what to do next.
Money gets one home
Status, balance, due date and the one action that matters, in a single card.
Four facts replace the term table
On a healthy policy the page goes quiet. No alert, nothing to act on.
Past and future terms move into a dropdown
Pick a term and every value above the tabs follows it.
Everything else gets a tab with one job
Nine tabs. Policy History is one timeline across every term, not just the one you’re on.
Ship it beside the old page
The new page arrives as an invitation from the old one, not a forced switch.
The delivery system
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.
Obie Homeowners
After the acquisition, an entirely new line of business in four months.
The quote is the product, so the quote lives on the page
Agents see their job as building a quote, the document they send their client. So I borrowed from product configurators, the way you build a car or spec a laptop: every choice in the workspace fills in the quote beside it, and the PDF they download is the one they watched take shape.
Agents have called it the smartest quoting interface they’ve seen.
Design is the work that makes it possible for the business, the builders and the people using it to end up wanting the same thing.
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.