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.
1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice.
Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 60,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation.
We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.
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The opportunity is massive: U.S. healthcare infrastructure is outdated, often requiring manual processes and interactions with systems that pre-date modern APIs.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
We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience.
Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.
Headway employees work remotely across the US, with the option to work from offices in New York City, San Francisco and Seattle. Headway participates in E-Verify. To learn more, click here.
