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# Senior Engineering Manager, Billing Infrastructure

- **Company:** Headway, LLC
- **Location:** New York, NY, United States
- **Experience:** Expert
- **Salary:** $265,200.0 - $331,500.0
- **Contract:** Permanent contract
- **Skills:** Adobe InDesign, Application Programming Interfaces (APIs), Data Integrity, Distributed Systems, Workflow Management Systems, State Machines, Backend, Event Driven Architecture, Data Pipelines
- **Published:** September 9, 2026
- **Apply:** https://www.indeed.com/viewjob?jk=a251a50a08e00eea

## About the Role

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 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.

 * 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 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 strong prioritization and roadmap judgment and can sequence work across a chain of dependent migrations while managing real cross-team dependencies.

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.

## Description

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., 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., Below are experiences we think help senior engineering managers succeed in this role