Senior Engineering Manager (Billing Infrastructure)

Join Headway as a Senior Engineering Manager for our Billing Infrastructure. In this high-leverage platform role, you will lead the technical strategy for the Billing System platform and drive its next chapter. You will work closely with Engineering Leadership, Product, Data, Finance, and Accounting to define how Headway records, moves, and stands behind its money. This is a platform-definition role, not a cleanup role, and requires strong prioritization and roadmap judgment, as well as a track record in domains where data integrity and financial correctness were the product.

• Lead the development and implementation of the new orchestration layer, a codified financial state machine for an appointment’s financial lifecycle.
• Own the technical strategy for the Billing System platform and drive its next chapter, including the design and governance of the state machine.
• Set technical direction across state-machine design, immutable snapshot and explainability guarantees, shadow-mode simulation, and a path toward durable workflow orchestration.

• 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