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.
The scheduling evidence is scattered across the same moment clinicians need to trust.
Fast investigation protects provider confidence, while unverified causal guesses risk sending engineers toward the wrong fix.
Who you’d be doing this for
“A patient asked why I sent two confirmations, and I had to reassure them the appointment was real.”
Dulce Moreno · Independent Mental Health Clinician · a character in this brief
Runs a solo outpatient practice and uses scheduling and provider messaging to manage patient appointments.
What is at stake
Patients are receiving duplicate confirmations for a single appointment, leaving clinicians to explain conflicting messages. You must decide how far Eddy carries a failure from the confirmation symptom through the Datadog traces and Sentry events, and which link in that chain an on-call engineer confirms in person.
Why it isn’t already fixed
Every obvious fix costs something else. That’s the part you’d have to decide.
- broad trace evidence vs trace gaps
- clinician-facing messages vs internal alert noise
- shared platform reuse vs workflow-specific learning
- on-call workload vs investigation depth
Why Headway
Scheduling and provider messaging sit inside the daily practice workflow clinicians use to manage patient care.
Written with these in mind
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)
- Real feedback from therapists and patients is worth more than another round of design review.
- The Modern AI-enabled Clinical System: Help design and build the interfaces and systems that manage clinical data.
- Staff Software Engineer (Journeys) (opens in a new tab)
- An engineer who has shipped high-throughput, event-driven systems in production and knows what reliability requires
- We’re building the next chapter: an agentic communications engine that learns which message, which channel, and which timing works best for each person — and gets smarter with every send.
- Staff Software Engineer - Experimentation (opens in a new tab)
- You will work closely with Data Science, who own statistical methodology, and with the teams who own our event tracking and metric definitions, because a number is only as trustworthy as the weakest link in that chain.
- Headway is a multi-sided marketplace, so we frequently need to change something for therapists and measure what happens to patients, which changes both how a test must be designed and how it can be analyzed.
- Engineering Manager (Provider) (opens in a new tab)
- Practice Management is a new team inside Provider Experience, forming in Q4 2026 to own the tools providers use every day to run their practice: calendar, messaging, notifications, and the home page of our EHR.
- 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.
- Senior Engineering Manager, Web Platform (opens in a new tab)
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.
Where similar work appears
Other live briefs connected to this one, and what connects them.
Similar problems at other organizations
Like this one, each of these is about people starting something and never quite finishing it.
Members are receiving coverage answers that later conflict with provider or billing records.
You must decide where the agent's cause ranking stops and where an engineer's confirmation of the trace, Context Engine record, and integration response begins.
Incorrect confirmations are sending patients into clinic callbacks and invalid appointment slots.
You have to weigh rapid restoration against the proof needed before changing a live scheduling workflow.
A customized client workflow fails, and engineers cannot quickly agree which event changed its path.
You must decide where the system's ranking of candidate causes ends and where an engineer's own check of the cited events begins.
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.
New clinicians are missing first appointments after completing early onboarding steps.
You must decide whether AI drafts explanations from evidence or only assembles the evidence for PM review.
Virginia clinicians are unsure whether their enrollment records are complete before January 29.
You must decide which readiness signals prompt action without implying payer approval.
Clinicians are receiving lower payments while claim records still look processed.
You must choose which suspected downcodes can move automatically and which need human review.
Other problems with a similar purpose
In each of these, as in this one, the aim is to find the real question hiding behind incomplete evidence and choose a reversible next step instead of guessing.
Product managers read homeowner, pro and metric evidence on urgent repairs separately and reach different conclusions.
You have to decide where the AI's clustering of that evidence stops and a product manager's framing of the problem begins before a test is shaped.
A major advertiser may move $1.5 million after finance disputes whether reported sales were incremental.
You must weigh a compelling cross-format growth case against the evidence each claim can support.
A 4,000-seat business program may not renew because executives dispute what learner progress proves.
You have to weigh a fast commercial save against claims the evidence cannot support.
