Senior Engineering Manager leading Headway's billing infrastructure platform, owning financial state machines and orchestration layer for 1.5M+ monthly appointments.
1 in 4 people in the US have a treatable mental health condition, but most providers don't 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. We've automated that.
But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 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. We aren't just a billing layer; we are becoming the platform where care actually happens.
We're 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.
The Role Lead the platform that owns what Headway believes about the money on every appointment, and when anyone is allowed to act on it. Help drive building our new orchestration layer, a codified financial state machine for an appointment’s financial lifecycle: explicit states, enforced guardrails, automated reconciliation, immutable explainability, and safe simulation of financial logic. A senior, high-leverage platform role at the center of every financial system at Headway, with a documented charter and a direct line to how quickly the company can close its books.
About Engineering at Headway Building a new mental healthcare system at Headway is only possible because of the scale and leverage that software can provide.
About this role Every appointment on Headway has a financial story: what the patient owes, what the provider is paid, what the payer is billed, and whether all three ever line up. At 1.5M+ appointments a month, up from 5.6M appointments in all of 2023 to 14.5M in 2025, that story has to be told correctly, automatically, and the same way every time.
As Senior Engineering Manager, you’ll own the technical strategy for the Billing System platform and drive its next chapter. Our new orchestration layer: the codified state machine that knows what state every appointment is in and what actions are allowed next is in design phases now; you’ll play a key role in building and planning from initial to full governance. Beyond orchestration: guardrail APIs that gate other systems’ writes, automated payer remittance ingestion, automatic refunds and recoups, and the non-happy-path machinery (refilings, fee-schedule corrections, settled state that has to reopen and re-settle safely) where the real engineering difficulty lives. You’ll set technical direction across state-machine design, immutable snapshot and explainability guarantees, shadow-mode simulation, and a path toward durable workflow orchestration, while partnering with Finance and Accounting, who consume your system’s output as the company’s financial record.
This is a platform-definition role, not a cleanup role. The billing system already exists and already commits real financial outcomes; the mandate is to extend it into the authority that governs when every financial action can happen, at 1.5M+ appointments a month and accelerating. Who you are We’re looking for a senior engineering leader with the technical depth to shape a complex financial platform and the organizational credibility to govern it. You’ll work closely with Engineering Leadership, Product, Data, Finance, and Accounting to define how Headway records, moves, and stands behind its money. Below are experiences we think help senior engineering managers succeed in this role:
Nice to have: ledger, double-entry, invoicing, or reconciliation systems experience; healthcare billing or EDI exposure; fintech or payments background; experience through external audit or a financial close-cycle transition; has built simulation, shadow-mode, or backtesting infrastructure for consequential financial logic.
Our interview process After you apply to Headway, here are some details of what to expect during the interview process.
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