Megan Casebier

← Part One: The Delivery System · Part Two: The Handoff → · The Policy Page

The Policy Page

Redesigning one of Obie’s most-visited pages so the answer is on screen when it loads, and building the working prototype engineering now ships it from.

Role
Senior Product Designer
Timeline
Aug 6 – Oct 15, 2026
Team
Product, design, engineering, with underwriting and servicing
Status
In build: production, behind a flag

Figures verified as of October 2026

Same policy · pending cancellation · agent view

The redesigned policy page: a banner reading 'This policy is pending cancellation at the insured's request, effective Sep 18, 2026', four fact cards, a tab bar, and a billing card on a grey ground. 1 2 3 4 5
  1. Servicing actions get a labelled button instead of a three-dot menu.
  2. One banner says what is happening to the policy, why, and when.
  3. Four cards hold the facts an agent checks first.
  4. Everything else moves into tabs, one subject each.
  5. Billing has one fixed home: balance, due date, and how to pay.
Captured from the working prototype at 1440px. Every policy, person and address in it is fictional.

The page everyone opened, and nobody could read

After a policy is bound, the policy page is where agents, clients and Obie’s own staff go to check on it. It drew about 20,000 visits a month, and it sat in the middle of nearly every servicing workflow.

It answered almost nothing at a glance. Was this policy cancelling? Why, and from when? What was owed, and when would autopay run? The answers were there somewhere, behind scrolling, a table of terms and a three-dot menu. So agents stopped looking and asked us instead.

Figures from the product team’s problem statement and M1 brief.

The page also carried enough design and technical debt that small fixes were hard to justify. The brief put it well: there’s no point fitting a nice new shower head in a bathroom that needs a full remodel.

Answer three questions before anyone scrolls

Every one of those requests was a question the page could have answered. We wrote the first milestone around the three that came up most.

  • What’s happening to this policy? Status, plus the reason and the date, in plain language.
  • What’s owed, and when? Balance, due date and billing type, always in the same place.
  • What can I do about it? The next action, named, one click away.

Six decisions that shaped the page

Headline news

One banner, and it tells the truth

A status pill can only say “Pending cancellation.” The banner says why and from when, in a sentence an agent can read aloud to a client.

It also has to correct the status when the status is misleading. A policy that’s been cancelled and rewritten, or moved to a new carrier, shows a frightening status even though coverage carries on. In those cases the banner leads with the reassuring fact and links to the new policy.

We worked the copy line by line with underwriting and servicing. “Continue,” not “resume,” because resume implies a gap. Banners never stack, and each one belongs to a single term and audience.

Old pagePending cancellation

Amber banner: This policy is pending cancellation at the insured's request, effective Sep 18, 2026.
Blue banner: This policy was rewritten. Coverage under a new policy will go into effect on Aug 25, 2026. Button: View new policy.
Blue banner: The renewal offer for this policy is ready to review. Review your offer and confirm payment by Aug 29, 2026 to avoid a lapse in coverage. Button: View renewal offer.
The old pill, then the sentences that replace it: cancellation, rewrite, renewal. Warm tone for bad news, cool tone when coverage continues

Billing

Money gets one home

Early drafts stacked billing messages on top of status banners. Servicing asked us to keep payment collection from feeling pushy, so we split the jobs. Banners carry policy status only. Billing lives in one card, in the same spot on every policy, whatever state it’s in.

A paid-up policy shows a quiet card. A past-due one shows the balance, the due date and a Pay now button, without a banner shouting about it.

Billing Status card marked Paid, outstanding balance $0.00, with an Update payment method button.
Billing Status card marked Past due, outstanding balance $414.00 due Aug 5, 2026, with a Pay now button.
Paid · autopayActive, but past due

Above the tabs

Four facts replace the term table

The old page opened with a table of every term, date and billing status. Most of the time an agent only needed one row of it.

Now four cards hold what gets checked first: status and policy number, the client, the premium, and the effective and expiry dates. When nothing is wrong, the page stays this calm. It doesn’t invent a banner to fill the space.

A quiet policy header: address, term dropdown, Policy actions button, and four cards showing Active status, client Evelyn Salt, the annual premium, and the effective and expiry dates.
An active, paid policy. No alert, nothing to act on

Terms

Past and future terms move into a dropdown

Each term is listed with its own policy number and status. Opening a policy always lands on the term that’s in force today, even when a renewal or rewrite is waiting. The banner links forward to it.

Looking at a past or future term turns on a time-travel bar, so nobody mistakes last year’s numbers for this year’s.

Switching terms on a five-term cancel-and-rewrite chain. Every value above the tabs follows the term you pick

Tabs

Everything else gets a tab with one job

Coverages, Property Details, Additional Parties, Documents, Claims and Policy History each take what used to be scattered down one long page. Tabs with nothing in them disappear.

Two fixes for long-standing complaints: coverages printed exactly as the declarations page shows them, so nobody has to open a PDF, and a billing ledger with a running policy balance.

A tour of the tabs on the busiest policy in the cast
Coverages tab: a two-column table of limits and deductibles.
Coverages — every limit and deductible from the dec page
Billing ledger: event, date, payment method, amount, and running policy balance.
Billing ledger — payments in brackets, a running policy balance on every row
Property Details tab with dwelling characteristics and the inspection disclaimer beneath.
Property Details — the same fields agents see when quoting, with the legal disclaimer underneath
Policy History table listing endorsements, refunds and renewal events across all terms.
Policy History — one timeline across every term, not just the one on screen

Rollout

Ship it beside the old page

A page this central can’t change for everyone overnight. The plan is opt-in: the old page offers the new one, the new page keeps a “View legacy policy page” button, and people move across when they’re ready.

We designed the bridge as carefully as the destination, down to the button copy.

The old policy page with a green bar reading 'Try out our new policy page' and a button 'Take me there, I'm stoked!'
The invitation on the old page

Engineering is building from the prototype

I built the design as a working app rather than a clickable mockup, on the platform’s real data shapes, with a fictional cast of policies covering every state in the spec. Engineering has the repository as well as the live link.

Engineering’s production spec is written from the prototype. The tab structure, the banner inventory word for word, the billing vocabulary and the ledger rules all carry straight across, down to example amounts taken from the prototype’s fictional policies. The first production pull request has merged: the page shell, the tab registry and all nine tabs, behind a feature flag. Engineering rebuilt it in the production stack; what carried across was the product, not the code.

“I wanted to build something eng could actually adopt instead of redo.”

From my note to the product team after the first full walkthrough
In the prototypeIn engineering’s production spec
Nine tabs in a fixed order, hidden when they have nothing to showThe same nine tabs in the same order, each gated by who’s viewing
Banner copy and tones worked out with underwriting and servicingA banner inventory with the same wording, line for line
Billing statuses: Payment due, Past due, Paid, No balance due, Refund owedOne shared vocabulary with the same five labels
A ledger with payments in brackets and a running policy balanceThe same display rules, using the prototype’s example amounts
Agent, client and internal views of one pageCapabilities decide who sees each banner, tab and action
An invitation on the old page and a way back on the new oneA legacy/new switch saved per browser, defaulting to legacy
One page, three audiences. As a client, Policy History drops away; internally, an Underwriting tab appears

How this became the team’s workflow, three projects in, is Part Two →

From walkthrough to production code

  1. First build: header, alerts and the first tabs

  2. Full prototype walked through with the product team

  3. Final stakeholder walkthrough of the first milestone’s specs and designs

  4. Cross-functional sign-off requested on milestone one

  5. Demoed company-wide with three live scenarios: a cancellation, a renewal offer and a conversion

  6. Engineering’s production spec written from the prototype; first production PR merged behind a flag

  7. Approved final design built end to end in the prototype

  8. Engineering building the production page and billing ledger, with the prototype as reference

The real test comes after release. The measure that matters is the one we started with: how many agents still have to write in each week about cancellations, billing and renewals.

Next on the list: richer claims details, a policy history with filters and friendlier descriptions, and documents organised by term.

What I took from it

A status needs a sentence

“Pending cancellation” is data. People need to know why, from when, and whether they’re still covered. Pair every alarming status with the sentence that explains it.

Give money one place

When billing moves around depending on the policy’s state, people hunt for it. When it always sits in the same card, they glance.

Prototype in the real shape

Building on the platform’s real data shapes, with every state covered, meant engineering could adopt the work instead of redrawing it from a mockup.

Made with a product manager, a second product designer, an engineer who set up its hosting, and partners across underwriting, servicing and engineering. All data shown is fictional.