Senior Director of Claims Operations

The Opportunity

As Director of Claims Operations for Sidecar Health, you will own and scale the engine that delivers our core promise to members. This team is responsible for all member-facing and provider-facing claims operations, clinical programs, and claims automation strategy – powering a consumer-driven major medical insurance model that's redefining how Americans access and pay for care.

This is a high-stakes, high-opportunity role at an inflection point: we're expanding into new markets, deepening our AI-enabled automation stack, and building the claims infrastructure to support a rapidly growing membership base. You will lead a multidisciplinary team, shape the technology roadmap alongside Product and Engineering, and drive the operational excellence and compliance rigor that our members and the business depend on.

If you have a proven track record in health insurance claims leadership and a history of using AI and automation to transform operations — not just optimize them — we want to talk.

What You'll Do

• Build & Lead a High-Performance Claims Operation (50%)
• Lead and scale a multidisciplinary Claims Operations team — spanning claims adjudication, quality, operations, and clinical — to drive accurate, timely claims processing and an exceptional member experience
• Foster a culture of metrics-driven continuous improvement, accountability, and high performance across all Claims functions
• Develop future leaders within the team and build the bench for a growing, complex operation
• Drive AI, Automation & Technology Strategy (30%)
• Own and execute the claims automation roadmap in close partnership with Product, Engineering, and Data Science teams
• Identify and prioritize opportunities to apply AI, machine learning, and workflow automation to reduce manual touchpoints, accelerate adjudication, and improve accuracy
• Champion a test-and-learn culture to validate automation hypotheses and scale what works
• Ensure Regulatory Compliance & Quality Assurance (20%)
• Ensure claims operations comply with all applicable state and federal regulations, including ACA, ERISA, and market-specific requirements
• Partner with Legal and Compliance to design and implement controls, audits, and governance structures
• Own quality assurance programs, including clinical review protocols, fraud detection, and claims accuracy standards