About the role:

We're looking for a Staff Product Manager to own our benefits platform and drive insurance accuracy for Headway.

As the product manager for our Benefits Platform, you'll be responsible for building the engine that determines patient eligibility, benefits, and cost estimates. You'll own the strategy to make insurance "wildly predictable" for patients and providers by evolving our platform from rules-based logic to ML-powered decision making. Working with Engineering, Data, Ops and Payer teams, you'll tackle complex healthcare data interpretation challenges and build systems that process millions of eligibility determinations with high accuracy.

What you'll do at Headway:

Own the benefits determination platform strategy and roadmap to achieve company goals for billing accuracy and collections loss reduction. Build ML-powered systems that interpret complex insurance data and handle thousands of payer-specific edge cases. Drive technical decisions on platform architecture, model deployment, and system scalability with engineering leadership. Collaborate with Engineering and Data Science on developing models that improve benefits interpretation accuracy and confidence scoring. Partner with Insurance Operations and Customer Care to understand manual intervention patterns and automate high-volume workflows.

You'll be great for this role if you:

Platform and ML experience: You have 6+ years building platforms that leverage ML for automated decision-making, preferably in healthcare, insurance, or adjacent risk domains. Healthcare or insurance background: You understand the complexities of health insurance - from claims processing to benefits determination - and have built systems that improve billing accuracy or clean claims rates. Technical depth: You're comfortable diving deep with engineering and data science teams on complex technical problems and can drive architectural decisions for scalable platforms. Cross-functional leadership: You've led initiatives requiring difficult tradeoffs between accuracy, speed, and user experience, and can influence stakeholders across multiple teams. Data-driven problem solving: You excel at analyzing complex datasets to identify root causes and drive systematic improvements to platform performance.

Compensation & Benefits:

The expected base pay range for this position is $215,900 - $254,000 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

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