About the Insurance Team

We’re looking for a passionate product leader to own and scale Headway’s Platform — the core engine of our business and the infrastructure that the rest of Headway is built on. You’ll lead an org with 10+ teams across core insurance and the broader platform and be a key member of the product leadership team guiding the broader company strategy. You’ll be responsible for key drivers of the provider, patient and payer experience as well as driving key financial outcomes for the company.

Insurance is at the crux of Headway’s mission to make quality mental health care affordable and accessible. Our ability to process benefits and claims efficiently and reliably determines whether patients and providers experience Headway as seamless — or frustrating. As the product leader at the helm of our platform, you will execute against the 12-month strategy already in motion, while setting a bold vision for how next-generation technology can reinvent the archaic systems our industry still depends on. You’ll also lead other core areas of the Headway platform, including payments, billing infra, customer support and trust.

The opportunity is massive: U.S. healthcare infrastructure is outdated, often requiring manual processes and interactions with systems that pre-date modern APIs. At Headway, we don’t just want to evolve incrementally — we want to fundamentally rethink how insurance works, reshaping cost structures and creating a magical experience for patients and providers. If you aspire to build platform products at scale, in one of the most complex and impactful industries, this is the role for you.

What you’ll do at Headway

Shape the next chapter of how Headway’s insurance platform evolves, leveraging cutting-edge technology. Lead, grow, and inspire a team of 10+ PMs, with future headcount expansion expected. Build core infrastructure for claims processing, eligibility, payments, and risk that power Headway’s business and customer experience. Tackle complex integrations with legacy insurance systems while designing future-facing solutions that reimagine how insurance should work. Provide scalable infrastructure that enables other product and engineering teams to build quickly and with confidence. Partner with cross-functional teams (engineering, design, data, compliance, and business stakeholders) to deliver measurable business impact.

You’ll be great for this role if you:

Platform Product Leader: You have 10+ years of experience in platform or infrastructure product roles (e.g., risk, credit, underwriting, payments), with 6+ years of people management experience. Systems Thinker: You love solving complex, interconnected problems and building systems that scale across a business. Growth-Stage Operator: You have experience operating at growth-stage startups, balancing execution with long-term strategy. Ambiguity Ready: You thrive in environments where the problems are messy, the systems are archaic, and the opportunity is wide open. Motivated by Impact: You care deeply about building products that meaningfully impact patients, providers, and the healthcare system at large. Empathetic Leader: You can inspire, coach, and grow teams while serving as a strong cross-functional partner. Healthcare Curious (bonus): Direct healthcare or insurtech experience is a plus, but not required.

The expected base pay range for this position is $297,500 - $350,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for performance-based variable compensation and an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

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