Engineering Manager (Claims)

Join Headway, a mission-driven company focused on improving mental health care access. As an Engineering Manager, you'll lead a team within our insurance platform, responsible for turning raw insurance data into accurate, real-time answers about coverage, cost, and payment. You'll co-own the roadmap with your product partner, make architectural decisions, and ensure operational health. Ideal candidates have 3-5+ years of software engineering experience, a passion for mission-driven work, and experience in healthcare, insurance, claims, or payments platforms.

• Lead an engineering team responsible for the development and maintenance of systems that turn raw insurance data into accurate, real-time answers about coverage, cost, and payment.
• Co-own the roadmap with your product manager, making architectural decisions, build-vs-buy trade-offs, and setting the standard the team operates to.
• Manage engineers, providing direct, kind feedback, and fostering a culture of growth and high performance within the team.
• You've managed engineers for 2+ years — whether as a tech lead with a handful of reports stepping into a bigger scope, or as a manager who has already run an engineering team through a scaling moment
• You give direct, kind feedback. You've told someone a hard truth and left the relationship stronger for it
• You're energized by mission-driven work. You see how better insurance infrastructure is better access to mental health care
• You have 3–5+ years of experience as a Software Engineer and came up as a builder. You're comfortable in a design review, you read PRs when it matters, and your team trusts your technical read
• You're a builder of intelligent systems with the right leverage — comfortable evaluating where automation, prediction, or AI belongs, and where it doesn't
• You've built systems other teams depended on — services, APIs, pipelines, or third-party integrations — at meaningful scale. You think clearly about failure modes and treat reliability as a feature, not an afterthought
• Healthcare, insurance, claims, or payments platform experience
• Experience partnering closely with operations or support teams to build tooling that scales human work
• Production ML or data-platform fluency — enough to evaluate, challenge, and partner credibly
• Scaleup experience, Series B through D
• We expect our engineering managers to remain active technical contributors — pairing with engineers, driving key design decisions, and personally owning select deliverables. You'll lead through doing, not just directing