Megan Casebier

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.

Case study · Part two · Obie, 2026

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.

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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

Weeks from design start, 0–32Approximate

Design decisions · Obie, 2026

The policy page

The page everyone opened and nobody could read. Six decisions so an agent can answer three questions before they scroll.

A banner: this policy was rewritten, with the date new coverage takes effect and a button to view the new policy

One banner, and it tells the truth

The status pill becomes a sentence: what happened, when, and what to do next.

Billing status card marked past due, with the balance, the due date and a Pay now button

Money gets one home

Status, balance, due date and the one action that matters, in a single card.

A quiet policy header with four facts: status, client, premium and dates

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.

The Policy History tab: one timeline across every term

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.

The old policy page with an invitation to try the new one

Ship it beside the old page

The new page arrives as an invitation from the old one, not a forced switch.

Read all six decisions, and how they reached production

Case study · Obie, 2023

From 496 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.

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The Leads tab with the details drawer open, showing fictional data

Design · Obie, 2025–26

The agent quote builder

The quote builder: on the left, the quote document with every coverage and deductible; on the right, the controls that set them
The design: choices on the right, the quote document taking shape on the left (Nov 2025). The first release, in February 2026, put the quote PDF inside customization.

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.

Case study · Obie, 2026

Breaking the Handoff

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.

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Slide from the talk, Early AI adventures: four solo AI experiments and how each one ended

Case study · Obie, 2025–26

Obie Homeowners

After the acquisition, an entirely new line of business in four months, launched in April 2026.

Through week 16, about 68% of leads became quotes.

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Choosing a package: two homeowners packages side by side, each with its annual premium, and the nine quote steps down the left

Case study · Part one · Obie

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.

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Megan Casebier

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.

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