Engineering Manager (Insurance)

Headway•San Francisco, NY

17h•Remote

About The Position

Headway's mission is to build a new mental healthcare system that everyone can access 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 experience of finding a therapist, and building scalable platform foundations. 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. This role is within the insurance platform team, focusing on the systems that provide real-time answers about coverage, cost, and payment. Depending on background, the role could lead teams responsible for payer communication, patient benefits determination, issue correction, or internal tooling for operations. This is a critical infrastructure role. The Engineering Manager will lead an engineering team end-to-end, co-own the roadmap with a Product Manager, and report to a senior manager. Managers are expected to lead through technical credibility in design reviews and be close to the work.

Requirements

3-5+ years of experience as a Software Engineer, with a background as a builder.
Comfortable participating in design reviews, reading PRs when important, and having a technical read that the team trusts.
2+ years of experience managing engineers (either as a tech lead with direct reports or as a manager who has led a team through scaling).
Experience building systems (services, APIs, pipelines, or third-party integrations) at meaningful scale that other teams depended on.
Ability to think clearly about failure modes and treat reliability as a feature.
Experience building intelligent systems with leverage, evaluating where automation, prediction, or AI is appropriate.
Ability to give direct, kind feedback and strengthen relationships through difficult conversations.
Energized by mission-driven work and understanding how better insurance infrastructure leads to better access to mental health care.

Nice To Haves

Experience in healthcare, insurance, claims, or payments platforms.
Experience partnering closely with operations or support teams to build scaling tooling for human work.
Production ML or data-platform fluency sufficient to evaluate, challenge, and partner credibly.
Scaleup experience, specifically Series B through D.

Responsibilities

Lead an engineering team, including hiring to a high bar, growing team members, and setting the team's culture.
Own a significant part of the insurance platform, which is depended upon by other Headway teams.
Co-own the roadmap for your team's surface area with your product partner.
Drive technical direction, including architectural decisions, build-vs-buy trade-offs, reliability targets, and setting team standards.
Partner cross-functionally with leaders across the insurance group (benefits, eligibility, claims, corrections) and adjacent groups (patient billing, payer partnerships, data platform) to ensure system coherence.
Ensure operational health, including incident response, on-call sustainability, and establishing a predictable planning rhythm for predictable shipping, especially during high-stakes periods like annual plan resets.
Remain an active technical contributor by pairing with engineers, driving key design decisions, and personally owning select deliverables.