Breaking the Handoff
Agency onboarding and an agent-portal sprint: what changed when product, design and engineering started together, and how we’re using the time AI gave us back.
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.
From a pile of quote requests to one list of people and homes
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.
Obie Homeowners
After the acquisition, an entirely new line of business in four months, launched in April 2026.
After launch, the error rate fell sharply within weeks.
The agent quote builder
The quote is the product, so the quote belongs on the page
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.
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.
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 diff that audited the design system
Machine-checking design tokens found a bug every human eye had passed for years.
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.