Engineering Manager (Revenue Engine)

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. Revenue Engine is the group that owns it. We're the systems of record and the systems of movement for Headway's money: the billing platform that decides and commits what everyone owes, and the claims platform that exchanges that truth with every payer we work with. When we're right, providers get paid on time, patients get bills they can trust, and Headway can close its books quickly. When we're not, a person has to figure out why; today, more often than we'd like, that's exactly what happens.

Responsibilities

An engineering team: hiring to a high bar, growing the people on it, and setting the culture your team operates by; A core surface of Headway's financial systems: a platform other teams depend on, and a roadmap you co-own with your product partner; Technical direction: architecture, build-vs-buy trade-offs, reliability targets, data-model decisions, and the standard the team operates to; Correctness and operability: the metrics that define "right" for your domain, the observability to prove it, incident response and on-call, and the steady conversion of manual toil into automation; Cross-functional partnership: with the other Revenue Engine teams, with the platform teams whose inputs and outputs you depend on (benefits, payments, payouts, corrections, claims operations), and with Finance and Accounting, who consume your systems' output as the company's financial record.

Requirements

3+ years of experience as an Engineering Manager, building and leading teams that delivered business outcomes through technical investment; 3–5+ years of experience as a Software Engineer, with depth in backend and distributed systems: event-driven architectures, workflow orchestration, or high-reliability data pipelines; You've led work where correctness and data integrity were non-negotiable (financial systems, payments, billing, claims, or a similarly consequential domain), including migrations you had to de-risk rather than simply schedule; You're comfortable defining "correct" in an ambiguous domain: setting the metric, instrumenting it, and defending it as inputs, counterparties, and volume change underneath you; You have strong prioritization and roadmap judgment, and you can sequence work for a small team against a clear metric while managing real dependencies on other teams; You're technical enough to be a credible thought partner in a design review, and you'd rather be close to the architecture of a money-movement system than removed from it; You've built durable partnerships with non-engineering stakeholders (operations, finance, or compliance) whose work depends on what your systems produce.

Nice to have

healthcare claims, EDI or clearinghouse experience; fintech or payments background; experience standing up observability and SLAs on a system that didn't have them; experience growing a small team into a larger one.

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