Something new at Headway

Flag gaps in treatment notes before a review sample is picked

Published Oct 22, 2026

You’re the software engineer. Your team is in the room.

The setting

is a marketplace and software platform that connects patients, health insurers and independent providers of mental health care across the United States. is the software therapists and psychiatric prescribers use to accept insurance and run their practice.

A pre-review signal can give clinicians clarity without turning documentation into a score-chasing exercise.

Providers need earlier visibility into documentation gaps, while clinical records must remain faithful to care rather than optimized for a checklist.

Who you’d be doing this for

“I only learned what they wanted after the review came back, and then I had to hunt through old notes.”

Sameer Rastogi · Licensed Clinical Social Worker · a character in this brief

A solo clinician using clinical notes and treatment plans to run an insurance-based practice.

What is at stake

Clinicians say they discover documentation expectations only after a note-review finding arrives. You must weigh useful early signals against pressure to turn clinical records into a compliance score.

Why it isn’t already fixed

Every obvious fix costs something else. That’s the part you’d have to decide.

  • early documentation clarity vs clinical judgment
  • provider confidence vs score-chasing behavior
  • fast first release vs high-integrity records
  • in-product guidance vs reviewer-owned interpretation

Why Headway

Treatment plans and progress notes sit at the center of the provider clinical system and the annual documentation review process.

Written with these in mind

product-minded fullstack engineerhealthcare workflow builderhigh-integrity systems engineer

Not your kind of problem? 104 more at Headway, or browse every organization.

Where the organization context comes fromThe postings this brief was written from, and the reporting read before it.

The organization context comes from public information. The situation and characters are written for the brief.

Job postings it was written from

Public descriptions of the work at Headway. They are listed as sources, not as openings. The lines under a posting are its own words, where it meets this brief.

  • Senior Fullstack Software Engineer (opens in a new tab)
    • Build high-integrity experiences for treatment plans and progress notes, integrating AI-powered clinical intelligence to give providers their time back.
    • You'll own features from the database schema to the UI, creating intuitive web experiences for scheduling, clinical notes, and payment management.
  • Staff Software Engineer (Journeys) (opens in a new tab)
  • Staff Software Engineer - Experimentation (opens in a new tab)
    • You will decide what our long-term experimentation and feature flagging stack should be; we run LaunchDarkly and Statsig today, and that architecture is yours to evaluate and consolidate.
    • You will gather needs from teams who all want something different, sequence them into a roadmap, and say no clearly, which means acting as part technical product manager for your own platform.
  • Engineering Manager (Provider) (opens in a new tab)
    • Supporting providers isn't just about connecting them with patients — it's about delivering the tools they need to manage their practice with ease, confidence, and compliance.
    • You get to play a leading role in defining what and how the team builds, setting up how it operates, supports, and ultimately drives best-in-class user experiences that have a measurable impact on our ability to execute and meet the demands of a high growth startup.
  • Senior Engineering Manager, Web Platform (opens in a new tab)
    • Build the automated checks and agent reviews that let that code ship with confidence.
    • You understand how designers work, and you can turn design system decisions into engineering plans.

This is the setup. The work is inside.

Running it puts you in the room: the full situation and its constraints, stakeholders who push back in their own words, and the decisions that are yours to make. What you produce becomes a Day One Plan — work you can show someone instead of describing.

Other live briefs connected to this one, and what connects them.

Similar problems at other organizations

Like this one, each of these turns on crossing a deadline that can't be undone.

The same setting, from another role

Each is set around Headway’s Headway for Providers, written for a different role. They’re separate briefs, not the same scenario.

Other problems with a similar purpose

In each of these, as in this one, the aim is turning fragile, failure-prone operations into systems people can quietly rely on when it matters most.