H
Headway
Senior Engineering Manager (Billing Infrastructure)
Skills
Compliance
1 month ago
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Important information
Contract type:
Permanent
Salary:
$265,200 – $331,500 / year
Location:
New York, NY, USA
Work mode:
Onsite
Published on:
24 September 2026
What they need
- 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
- 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
- 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- You have strong prioritization and roadmap judgment and can sequence work across a chain of dependent migrations while managing real cross-team dependencies
- You have a track record in domains where data integrity and financial correctness were the product: billing, payments, ledgers, claims, or a similarly consequential platform
- You’ve partnered with Finance, Accounting, or compliance functions whose work depends on what your systems produce, and you can make that relationship work when interests diverge
- You have 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
- You’ve led platform work whose customers are other engineering teams — defining contracts, setting standards, and getting peers to build behind guardrails rather than around them
- You have 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
- 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- Initial screen: You’ll connect with someone in recruiting so you can learn more about the team, Headway’s mission and exciting growth, and we can get a better idea of your background
- First rounds: You’ll meet with an engineering leader on the team to go deeper into your team and people leadership experiences
- Final rounds: You’ll meet team members across product and engineering leadership for multiple behavioral interviews and two technical interviews (System Design & AI Coding), leaving you with a fuller picture of what it’s like to work at Headway
- References and the Offer: Our favorite part of the process! We’ll send over all of the details, including specifics on employee equity, and congratulatory messages from excited future team members!
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