Engineering Manager (Insurance)

About the Team & Role

Mental health care shouldnt come with surprise bills and it shouldnt cost providers sleep wondering whether theyll get paid for the work they did. At Headway getting insurance right reliably accurately and in real time is the single most leveraged problem we solve. Its the difference between a patient who can afford their first session and one who cant; between a provider who chooses Headway and one who doesnt.

Were hiring an Engineering Manager to lead one of the teams inside Headways insurance platform the connected set of systems that turn raw insurance data into accurate real-time answers about coverage cost and payment. Depending on background and interest this role may lead the team responsible for any of: how we communicate with payers how we determine and represent a patients benefits how we correct issues when something downstream goes wrong or the internal tooling that lets operations teams work the long tail at scale.

This is infrastructure the rest of the company runs on. Youll lead an engineering team end-to-end co-own the roadmap with your PM and report to a senior manager who will give you the autonomy to run your team while being a close thought partner. Were a technical engineering org managers here lead through credibility in design reviews not through distance from the work.

What Youll 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.

Youd Be a Great Fit If

• You have35 years of experience as a Software Engineerand came up as a builder. Youre comfortable in a design review you read PRs when it matters and your team trusts your technical read.
• Youvemanaged 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.
• Youvebuilt 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.
• Youre abuilder of intelligent systems with the right leverage comfortable evaluating where automation prediction or AI belongs and where it doesnt.
• You givedirect kind feedback. Youve told someone a hard truth and left the relationship stronger for it.
• Youreenergized by mission-driven work. You see how better insurance infrastructure is better access to mental health care.

Bonus points for:

• 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. Youll lead through doing not just directing.