Engineering Manager, Benefits

Headway•San Francisco, NY

2d•Remote

About The Position

Headway is building a new mental healthcare system that is accessible to everyone by solving the insurance barrier. They have automated the administrative work involved in insurance, such as credentialing, claims, and payment reconciliation. Over 70,000 providers use their software, serving over 1 million patients. Headway is developing tools for therapists to manage their practices, improving the process of finding a therapist, and investing in platform foundations for scalability. They are a Series D company with over $325M in funding and are seeking exceptional individuals to help achieve their mission of transforming mental healthcare.

Requirements

5+ years of experience as an engineer, with a significant portion at a senior or staff level, maintaining technical credibility.
Early-stage management experience, such as leading a small team or a tech lead with direct reports.
Proven ability to build robust systems and understand complex system interdependencies.
Experience owning critical systems that other teams depend on.
Ability to identify deep problems and build intelligent, leveraged systems (e.g., using agents, predictive algorithms, rules, and infrastructure).
Experience using AI as a tool for solving business problems.
Energized by mission-driven work and the impact of improved mental health care infrastructure.
Experience giving direct, kind feedback.
Deeper machine learning fluency, including hands-on experience with eval loops, model rollout, or production ML systems (bonus points).
Experience in healthcare, insurance, or claims (bonus points).
Scaleup experience, particularly from Series B through D (bonus points).

Nice To Haves

Deeper machine learning fluency — hands-on experience with eval loops, model rollout, or production ML systems.
Healthcare, insurance, or claims experience.
Scaleup experience, Series B through D.

Responsibilities

Lead a team of 4-5 engineers, focusing on hiring, growth, and coaching.
Own the platform that is core to Headway's business, impacting patient bookings, provider payouts, and claims.
Co-own the roadmap with product, setting pace, priorities, and strategic bets for a key engineering team.
Establish technical standards and team culture, including work scoping, architectural decisions, incident response, and on-call practices.
Partner with leaders of claims, eligibility, billing, and payer partnerships to ensure system integrity.