Engineering Manager (Revenue Engine)

Headway•San Francisco, CA

4d•Remote

About The Position

Headway is building a new mental healthcare system to make therapy accessible and affordable by solving the insurance barrier. We've automated administrative tasks like credentialing, claims, and payment reconciliation. Over 75,000 providers use our software, serving over 1 million patients. We are developing tools for therapists, improving the process of finding a therapist, and investing in platform foundations for scalability. We are a Series D company with significant funding, seeking dedicated individuals to help us achieve our mission and provide the most meaningful career experience. Engineering at Headway is crucial for building this new mental healthcare system through software. Our guiding principles are focused on scale and leverage. The Revenue Engine team is responsible for the financial story of every appointment, ensuring accuracy in patient owes, provider payments, and payer billing. With millions of appointments monthly and projected growth, this team manages the systems of record and movement for Headway's finances, including billing and claims processing. The goal is to transition from systems that are largely correct to provably correct, explainable, resilient, and correct by construction. This involves tackling the complexities of inconsistent payer responses and defining system beliefs in ambiguous situations, making them auditable. Two Engineering Manager roles are available within Revenue Engine, each leading a team end-to-end with autonomy and close partnership. Managers are expected to lead through technical credibility in design reviews.

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.
Experience leading work where correctness and data integrity were non-negotiable (financial systems, payments, billing, claims, or a similarly consequential domain), including de-risking migrations.
Comfortable defining "correct" in an ambiguous domain: setting the metric, instrumenting it, and defending it as inputs, counterparties, and volume change.
Strong prioritization and roadmap judgment, with the ability to sequence work for a small team against a clear metric while managing dependencies on other teams.
Technical enough to be a credible thought partner in a design review.
Experience building durable partnerships with non-engineering stakeholders (operations, finance, or compliance) whose work depends on the systems' output.

Nice To Haves

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.

Responsibilities

Hiring to a high bar, growing the people on the team, and setting the team's culture.
Owning a core surface of Headway's financial systems, which is a platform other teams depend on, and co-owning the roadmap with a product partner.
Defining technical direction, including architecture, build-vs-buy trade-offs, reliability targets, data-model decisions, and setting the team's operational standard.
Ensuring correctness and operability by defining relevant metrics, implementing observability, managing incident response and on-call duties, and automating manual processes.
Building cross-functional partnerships with other Revenue Engine teams, platform teams (benefits, payments, payouts, corrections, claims operations), and Finance and Accounting, who rely on the systems' output as the company's financial record.

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