Senior Engineering Manager, Billing Infrastructure

Headway•Seattle, WA

2d•$265,200 - $331,500•Remote

About The Position

Headway's mission is to fix the mental healthcare system by building a new system everyone can access, starting with solving the biggest barrier to care: insurance. The company has automated the administrative work of credentialing, claims, and payment reconciliation. Over 75,000 providers across all 50 states run their practice on Headway's software, serving over 1 million patients. Headway is building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in platform foundations to enable this at scale. Headway is a Series D company with over $325M in funding from investors like a16z, Accel, and Spark Capital.

Requirements

5+ years of experience as an Engineering Manager, including experience leading platform or infrastructure teams at scope beyond a single team (multiple teams, a broad cross-org platform mandate, or both).
5–7+ years of experience as a Software Engineer with depth in backend and distributed systems: financial state machines, event-driven architectures, workflow orchestration, or high-reliability data pipelines in domains where correctness is non-negotiable.
Led platform work whose customers are other engineering teams — defining contracts, setting standards, and getting peers to build behind guardrails rather than around them.
Track record in domains where data integrity and financial correctness were the product: billing, payments, ledgers, claims, or a similarly consequential platform.
Partnered with Finance, Accounting, or compliance functions whose work depends on what your systems produce, and can make that relationship work when interests diverge.
Strong prioritization and roadmap judgment and can sequence work across a chain of dependent migrations while managing real cross-team dependencies.

Nice To Haves

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.

Responsibilities

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 Headway's new orchestration layer, a codified financial state machine for an appointment’s financial lifecycle, including explicit states, enforced guardrails, automated reconciliation, immutable explainability, and safe simulation of financial logic.
Own the technical strategy for the Billing System platform and drive its next chapter.
Play a key role in building and planning the new orchestration layer from initial to full governance.
Manage guardrail APIs that gate other systems’ writes, automated payer remittance ingestion, automatic refunds and recoups, and non-happy-path machinery (refilings, fee-schedule corrections, settled state that has to reopen and re-settle safely).
Set technical direction across state-machine design, immutable snapshot and explainability guarantees, shadow-mode simulation, and a path toward durable workflow orchestration.
Partner with Finance and Accounting, who consume the system’s output as the company’s financial record.
Extend the existing billing system into the authority that governs when every financial action can happen, at 1.5M+ appointments a month and accelerating.
Work closely with Engineering Leadership, Product, Data, Finance, and Accounting to define how Headway records, moves, and stands behind its money.

Benefits

Equity compensation
Medical, Dental, and Vision coverage
HSA / FSA
401K
Work-from-Home Stipend
Therapy Reimbursement
16-week parental leave for eligible employees
Carrot Fertility annual reimbursement and membership
13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
Flexible PTO
Employee Assistance Program (EAP)
Training and professional development