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Headway

Engineering Manager (Insurance)

Headway
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hybrid mid full-time $190,000 - $237,500 New York, New York, United States; San Francisco, California, United States; Seattle, Washington, United States

First indexed 4 Jun 2026

Description

We're hiring an Engineering Manager to lead one of the teams inside Headway's insurance platform. The successful candidate will lead an engineering team end-to-end, co-own the roadmap with their PM, and report to a senior manager. They will be responsible for technical direction, cross-functional partnership, and operational health.

The ideal candidate will have 3–5+ years of experience as a Software Engineer and have managed engineers for 2+ years. They should be comfortable in a design review, have built systems other teams depended on, and think clearly about failure modes and treat reliability as a feature.

The expected base pay range for this position is $190,000 - $237,500, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

Benefits offered include equity compensation, medical, dental, and vision coverage, HSA/FSA, 401K, work-from-home stipend, therapy reimbursement, 16-week parental leave for eligible employees, carrot fertility annual reimbursement and membership, 13 paid holidays each year as well as a holiday break during the week between December 25th and December 31st, flexible PTO, employee assistance program (EAP), training and professional development.

This listing is enriched and indexed by YubHub. To apply, use the employer's original posting: https://job-boards.greenhouse.io/headway/jobs/6013576004