Engineering Manager (Revenue Engine)

HeadwaySan Francisco, CA
$222,800 - $222,800Remote

About The Position

Headway is building a new mental healthcare system to make therapy accessible and affordable by solving the insurance barrier. We have automated the administrative work like credentialing, claims, and payment reconciliation. Over 75,000 providers use our software, serving over 1 million patients. We are developing tools for therapists to manage their practices, improving the process of finding a therapist, and investing in platform foundations for scalability. We are a Series D company with over $325M in funding and are seeking exceptional individuals to help us achieve our mission and make this the most meaningful experience of their careers.

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 (e.g., financial systems, payments, billing, claims), including de-risking migrations.
  • Comfortable defining "correct" in an ambiguous domain: setting metrics, instrumenting them, and defending them 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.
  • Technical enough to be a credible thought partner in design reviews, and a preference for being close to the architecture of money-movement systems.
  • Experience building durable partnerships with non-engineering stakeholders (operations, finance, or compliance) whose work depends on system outputs.

Nice To Haves

  • Healthcare claims, EDI or clearinghouse experience.
  • Fintech or payments background.
  • Experience establishing observability and SLAs on a system that lacked 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 a 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 standards.
  • Ensuring correctness and operability by defining metrics for the domain, implementing observability to prove them, managing incident response and on-call duties, and automating manual tasks.
  • Building cross-functional partnerships with other Revenue Engine teams, platform teams (benefits, payments, payouts, corrections, claims operations), and Finance and Accounting departments.

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
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