Senior Engineering Manager, Billing Infrastructure

Headway • New York, NY

1d • Remote

About The Position

Headway's mission is to fix the mental healthcare system by building a new system everyone can access. They have automated the administrative work of credentialing, claims, and payment reconciliation, and are building tools for therapists to run their entire practice. Over 75,000 providers use their software, serving over 1 million patients. Headway is a Series D company with over $325M in funding, seeking exceptional people to help achieve their mission and provide the most meaningful career experience. This role will lead the platform that governs financial transactions for every appointment, driving the development of a new orchestration layer that acts as a codified financial state machine for an appointment's financial lifecycle. This includes explicit states, enforced guardrails, automated reconciliation, immutable explainability, and safe simulation of financial logic. It is a high-leverage platform role at the center of Headway's financial systems.

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.
• Track record in domains where data integrity and financial correctness were the product: billing, payments, ledgers, claims, or a similarly consequential platform.
• Experience through external audit or a financial close-cycle transition.

Nice To Haves

• Led platform work whose customers are other engineering teams — defining contracts, setting standards, and getting peers to build behind guardrails rather than around them.
• Ledger, double-entry, invoicing, or reconciliation systems experience.
• Healthcare billing or EDI exposure.
• Fintech or payments background.
• 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 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.
• 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.
• Drive development of 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 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.
• Lead platform work whose customers are other engineering teams — defining contracts, setting standards, and getting peers to build behind guardrails rather than around them.
• Partner with Finance, Accounting, or compliance functions whose work depends on what your systems produce, and make that relationship work when interests diverge.
• Sequence work across a chain of dependent migrations while managing real cross-team dependencies.

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

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed