Engineering Manager

What You'll Own

• An engineering team — hiring to a high bar, growing the people on it, and setting the culture your team operates by.
• A meaningful surface of the insurance platform — a system other Headway teams depend on, and a roadmap you co-own with your product partner.
• Technical direction — architectural decisions, build-vs-buy trade-offs, reliability targets, and the standard the team operates to.
• Cross-functional partnership — working with leaders across the insurance group (benefits, eligibility, claims, corrections) and adjacent groups (patient billing, payer partnerships, data platform) to keep the whole system coherent.
• Operational health — incident response, on-call sustainability, and the planning rhythm that lets your team ship predictably through high-stakes moments like annual plan resets.

Requirements

• 3–5+ years of experience as a Software Engineer; comfortable in design reviews, read PRs, and team trusts technical judgment.
• Managed engineers for 2+ years — whether as a tech lead stepping into bigger scope or as a manager who has run an engineering team through a scaling moment.
• Built systems other teams depended on — services, APIs, pipelines, or third-party integrations — at meaningful scale.
• Think clearly about failure modes and treat reliability as a feature.
• Builder of intelligent systems with the right leverage — comfortable evaluating where automation, prediction, or AI belongs.
• Give direct, kind feedback; told someone a hard truth and left the relationship stronger.
• Energized by mission-driven work.

Nice-to-Haves

• 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.
• Scaleup experience, Series B through D.

Engineering managers are expected to remain active technical contributors — pairing with engineers, driving key design decisions, and personally owning select deliverables.