Senior Applied AI Enginner, AI Platform

1 in 4 people in the US have a treatable mental health condition, but most providers dont accept insurance, making therapy too expensive for most people. Headway's mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. Weve automated that.

But were going further. Over 90,000 providers across all 50 states run their practice on our software, serving over 2.6 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale, and building much of it with AI. We arent just a billing layer; we are becoming the platform where care actually happens.

Were a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

About Eddy at Headway:

Eddy is Headways in-house AI agent platform and the highest-leverage internal product weve shipped. It gives every Headwegian an agent harness pointed at Headways own systems: an isolated sandbox per conversation, tool access to the third parties we depend on, and the ability to turn any of it into something durable, like a shareable interactive app, a workflow, a scheduled agent, a Slack teammate, or a webhook-triggered automation. Today 850+ Headwegians use Eddy daily, and 40k+ scheduled agents and workflows run every week with no one in the loop.

We sit in Engineering Foundations and own all of it: the chat product, the agent loop, the sandboxed runtime, the tool and integration layer, the artifact and app platform, the workflow engine, the eval harness, and the safety and access-control model that lets this touch real production and healthcare data without causing incidents. Were a small team with a very large surface area.

About this role:

Self-serve gets a function most of the way. It doesnt get them all the way.

Legal still reads every provider contract and payer amendment by hand, because what would help isnt a chat window. Its a system that knows what a redline means here, what gets escalated, and what our position was the last four times. Credentialing, claims exceptions, and CX triage each have their own version: work that is obviously automatable but full of enough domain-specific detail that nobody outside the function can build it, and nobody inside can build it alone.

Thats this role. Youll embed with one function at a time and build them a real product on top of Eddy. Then youll do the harder half: work out which parts are specific to that function and which are primitives that belong in the platform, and land the primitives in Eddy so the next function gets them for free. Most quarters should end with a function measurably better off and a new capability in the platform.

What youll do:

• Find the real bottleneck. Sit with a function long enough to see the work, and define success in their terms: turnaround time, escalation volume, error rate, headcount avoided.
• Build the vertical. Skills, MCP integrations against their systems of record, subagents, scheduled and event-driven agents, artifact apps, and whatever product surface the workflow needs. You own it end to end.
• Ship in days, harden over weeks. Get a rough v1 in front of real users fast, then do the unglamorous work of making it dependable.
• Own it in production. Evals, tracing, cost and latency, failure modes. If a function depends on it, youre on the hook for it.
• Extract the primitives. Land the generalizable half in Eddy as a first-class capability, with tests and docs.
• Kill work that shouldnt exist. Some requests are better answered by a workaround, a config change, a process change, or nothing. Finding those is worth as much as building.
• Design for PHI from the start. Eddy operates inside HIPAA.

This is not solutions or sales engineering. Theres no deal cycle, and your users are colleagues. Its not a pure platform role either: youll spend real time inside other teams problems.

Tools we use:

Languages: Python 3, TypeScript

Frontend: React 19, React Router 7, Tailwind, Radix, TanStack Query

Backend & Storage: FastAPI, SQLAlchemy 2.0 (async), Alembic, Postgres, Redis, DynamoDB, Snowflake

AI: Claude Agent SDK, Anthropic API, Bedrock, LangSmith

Infrastructure: AWS, EKS (a hardened pod per session), EC2 + CodeDeploy blue/green, Temporal, Kafka, Cloudflare

Ops: Datadog, Sentry, PagerDuty, GitHub Actions

AI tools: Cursor, Claude Code, and Eddy itself. We build Eddy with Eddy.

Who you are:

• An end-to-end product builder who moves between a React surface, a FastAPI service, and a container image without a handoff.
• Serious about AI as engineering: tool use, agent loops, evals, context management, and cost and latency at volume.
• Someone who likes users you can see. Youve gravitated toward internal platform or developer tooling work, or taught something and enjoyed it.
• Able to hold a scope conversation: push back, renegotiate, say no, and leave people wanting to work with you again.
• A platform thinker who starts specific, and has the judgment to tell which half of a build is which.
• Comfortable owning outcomes with no spec and no backlog.
• Guardrails by instinct, and precise in communication with people who dont write code.

Experience were seeking:

• 5+ years shipping production software end to end.
• Has built and shipped LLM/agent-powered products to real users.
• Experience as a forward deployed engineer, solutions engineer, internal platform engineer, or founder is a plus, as is work on agent frameworks or developer platforms. Healthcare experience is not required, but you should be able to dive into an exception-heavy domain and build a working mental model fast, several times a year.

Youll love this role if you want to:

• See a real business problem through to a shipped product your colleagues depend on.
• Shape an AI platform from the outside in.
• Have the most cross-functional engineering role at Headway.

Comprehensive benefits:

Medical, dental, vision, HSA/FSA, 401(k) including match for 2027!, Carrot Fertility reimbursement, and paid parental, medical and caregiver leave.

We believe a teams strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem - across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.

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