One wrong line used to mean a whole new report

A whole template for one wrong line

Owl turns an insurance file into templates: claim summaries, timelines of key events, and the forms a reviewer would otherwise fill in by hand. Templates are what Owl’s customers pay for, and each one is shaped with the client field by field.

But a claim doesn’t stand still. New medical records arrive, a name turns out to be incomplete, a diagnosis gets corrected. The only way to update a template was to regenerate all of it, wait, and reread every field to make sure nothing else had moved. For reviewers and adjusters working through dozens of claims, that was slow and frustrating, and it made them hesitant to fix small things at all.

Designed with the people using it

We built this alongside Owl’s largest customer, a Fortune 500 disability insurer. Their reviewers walked us through real claims, showed us where templates went stale, and reacted to each round of designs against their own workflow. That set the brief: edits had to be ad hoc, small, quick to check, and never surprise anyone else on the claim.

Select, ask, keep

The interaction borrows from document editors people already know. Highlight any text in a template and two actions appear beside it: Improve and Explain.

Select anything. Highlight a line and Owl offers to improve it or explain where it came from.

Improve opens Owl Assist with the selection attached and the prompt already started, so the reviewer only has to finish the sentence: “include the claimant’s full name.” Explain answers the question reviewers ask most often, why a line says what it says, without touching the template. The conversation is scoped to whatever template is open, and anything can be typed free-form.

Ask in plain language. The selection becomes the context. The reviewer just says what’s wrong.

Owl makes the change across the template, not just in the selected line, and every edit waits for a decision. Reviewers can keep or undo each one, or the whole set at once. Nothing is committed until a person says so.

Scoping what we could ship

The ideal version showed every edit inline, struck through and highlighted like tracked changes. Owl’s tech stack at the time couldn’t support diff highlighting, so I worked with engineering to find the version that it could.

In the MVP, changes happen at the field level. Keeping a change keeps the whole field, and Owl only ever edits field values, never the names or titles the client had agreed to. Owl’s replies stayed simple too: a short confirmation of what changed, rather than a full walkthrough. It was a smaller feature, but it removed the full regeneration from a reviewer’s day.

A few product rules came out of that scoping, and they all held up later:

• Every edit is a version. There is no publish step to forget, and everyone sees the same template.

• Nothing is ever lost. Old versions are a click away, and restoring one creates a new version instead of erasing history.

• No locks. Anyone on the claim can edit. A template only one person can touch is a less useful template.

History. Conversations and template versions are kept, so any change can be traced and rolled back.

Coming back with diffs

After template editing shipped, I spent the next stretch of Owl designing Escalations: a workspace where Owl flags the problems in a file and works through them with you in conversation. That work moved the whole product forward, including the stack that had held the first version back.

So we went back to the client. We asked reviewers how editing had been going, what they still worked around, and where they hesitated before keeping a change. Then we brought Escalations’ conversational Owl Assist and inline diff highlighting to templates. Owl now shows its reasoning step by step as it works. Removed text is struck through, new text is highlighted, and every change has its own Keep and Undo.

Diffs on every field. One request updates every field it affects, and each change can be reviewed on its own.

Outcome

Fixing a template went from regenerating the whole thing to typing a single sentence. Reviewers could correct a name, add a missing detail, or ask why a line said what it did, without waiting on a full rerun or rereading fields that hadn’t changed. And because Owl only reworks what it is asked to, edits stay small and predictable.

Shipping the smaller version first paid off. By the time we returned, reviewers had months of real edits behind them, so their feedback was specific. The second pass went straight at what they asked for: seeing exactly what changed before keeping it.

Some details are simplified or left out to respect client confidentiality.