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HeadwayHeadwaySan Francisco, CA

Engineering Manager

Leads an engineering team responsible for Headway’s revenue and financial systems, driving technical direction, correctness, reliability, and automation. The role requires engineering management experience, backend and distributed-systems depth, and experience with high-integrity domains such as payments, billing, or claims.

223k – 223k/yr
Hybrid5+ YOEEngineering Management

About the role

Responsibilities

  • Lead an engineering team end-to-end, including hiring, developing people, and setting team culture.
  • Co-own the roadmap for a core surface of Headway's financial systems with a product partner.
  • Set technical direction across architecture, build-versus-buy decisions, reliability targets, and data modeling.
  • Define correctness and operability metrics, improve observability, lead incident response and on-call, and automate manual work.
  • Partner with Revenue Engine, platform, Finance, Accounting, Product, Data, and Operations teams.
  • Own systems supporting claims transmission and payer-response processing, or billing orchestration and immutable financial snapshots.

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.
  • Backend and distributed-systems depth, including event-driven architectures, workflow orchestration, or high-reliability data pipelines.
  • Experience leading work where correctness and data integrity were non-negotiable, such as financial systems, payments, billing, claims, or similarly consequential domains.
  • Ability to define correctness in ambiguous domains, establish metrics, instrument systems, and adapt as inputs and volume change.
  • Strong prioritization and roadmap judgment for sequencing work against clear metrics and dependencies.
  • Technical credibility in architecture and design reviews.
  • Experience partnering with non-engineering stakeholders in operations, finance, or compliance.

Nice to Have

  • Healthcare claims experience.
  • EDI or clearinghouse experience.

Compensation

  • Annual salary: $222,800

Skills

backend engineeringDistributed SystemsEvent-Driven ArchitectureWorkflow OrchestrationData Pipelinesfinancial systemsPaymentsbillinghealthcare claimsediObservabilityData ModelingIncident Responseon-call

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