Head of Engineering (Insurance) - Remote

Overview

Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance.

In Short

• Lead and scale the Insurance Engineering group at Headway.
• Ensure critical systems behind benefits, eligibility services, claims, and billing infrastructure.
• Guide and mentor engineering teams for high performance.
• Collaborate with product, design, and data teams for strategic alignment.
• Shape the engineering culture and processes as the team grows.
• Build a roadmap for the future of the Insurance Engineering group.
• Recruit and develop diverse engineering talent.
• Contribute to the company’s technical strategy.
• Drive company-level objectives with high-impact solutions.
• Facilitate cross-functional partnerships to enhance user experiences.

Requirements

• 8+ years of experience in engineering leadership.
• Strong technical foundation as a former Software Engineer.
• Ability to manage both high-level strategy and detailed technical challenges.
• Experience in building resilient and scalable platforms.
• Background in health tech or complex domains (insurance, payments).
• BS, MS in Computer Science or related field.

Benefits

• Equity Compensation.
• Medical, Dental, and Vision coverage.
• HSA / FSA.
• 401K.
• Work-from-Home Stipend.
• Therapy Reimbursement.
• 16-week parental leave.
• Flexible PTO.
• Training and professional development.