Engineering Manager – Revenue Engine

Jobtailor; California (MO); On-site; USD 140,000 - 180,000; Full time

Job summary

Headway is seeking an Engineering Manager to lead and grow a team, own a core surface of financial systems, and co-own the product roadmap with a partner. Define architecture, reliability targets, observability, and data models while converting toil into automation.

Build durable partnerships with operations, finance, and compliance to deliver reliable, scalable systems. This role requires a product-minded, data-informed leader with strong prioritization, and experience in payments or

Qualifications

• 3+ years leading engineering teams delivering business outcomes through technical investment.
• 3–5+ years as a Software Engineer.
• Experience with backend, distributed systems, event-driven architectures, or high-reliability data pipelines.
• Experience de-risking migrations.

Responsibilities

• Lead and grow an engineering team, including hiring, development, and culture-setting.
• Own a core surface of Headway's financial systems and co-own its roadmap with a product partner.
• Set technical direction across architecture, build-vs-buy decisions, reliability targets, and data models.
• Define correctness metrics, observability, incident response and on-call, and convert manual toil into automation.
• Partner with Revenue Engine teams, platform teams, Finance, Accounting, and other stakeholders.
• For Claims Platform: oversee claims transmission, payer-response interpretation, and faithful recording of claims outcomes.
• For Billing Infrastructure: oversee orchestration and immutable commitment of patient responsibility, payer responsibility, and provider payout.
• Lead technical design reviews while remaining close to system architecture and implementation.

Skills

Team leadership

Software engineering

Backend systems

Data integrity

Observability

Automation

Cross-functional partnerships

Job description

• Lead and grow an engineering team, including hiring, development, and culture-setting
• Own a core surface of Headway's financial systems and co-own its roadmap with a product partner
• Set technical direction across architecture, build-vs-buy decisions, reliability targets, and data models
• Define correctness metrics, establish observability, support incident response and on-call, and convert manual toil into automation
• Partner with Revenue Engine teams, platform teams, Finance, Accounting, and other stakeholders
• For Claims Platform: oversee claims transmission, payer-response interpretation, and faithful recording of claims outcomes
• For Billing Infrastructure: oversee orchestration and immutable commitment of patient responsibility, payer responsibility, and provider payout
• Lead technical design reviews while remaining close to system architecture and implementation

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
• Depth in backend and distributed systems, 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
• Experience de-risking migrations
• Ability to define correctness in ambiguous domains, set metrics, instrument systems, and defend standards as inputs and volume change
• Strong prioritization and roadmap judgment
• Technical credibility in architecture and design reviews
• Experience building durable partnerships with operations, finance, or compliance stakeholders
• Product-minded and data-informed approach
• Nice to have: healthcare claims, EDI, or clearinghouse experience
• Nice to have: fintech or payments background
• Nice to have: experience establishing observability and SLAs
• Nice to have: experience growing a small team into a larger one
• Authorization to work in the United States

Core Competencies

Demonstrates expertise in leading engineering teams and driving technical direction in financial systems, with a strong focus on data integrity, observability, and automation. Proven ability to build partnerships across operations, finance, and compliance while delivering business outcomes through strategic technical investments.