Engineering Manager (Insurance)

About the Team & Role

Mental health care shouldn't come with surprise bills, and it shouldn't cost providers sleep wondering whether they'll 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. It's the difference between a patient who can afford their first session and one who can't; between a provider who chooses Headway and one who doesn't.

We're hiring an Engineering Manager to lead one of the teams inside Headway's 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 patient's 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. You'll 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. We're a technical engineering org — managers here lead through credibility in design reviews, not through distance from the work.

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.

You'd Be a Great Fit If…

• 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'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'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.
• 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 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.

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. You'll lead through doing, not just directing.