Sidecar Health jobs

Sidecar Health is hiring a Field Support Manager for its Member Care team in Georgia/Ohio to oversee a team of approximately 10 field support agents. Responsibilities include managing team productivity and performance, acting as escalation point for complex member issues, ensuring team morale, coordinating agent movements and field activities, and working with training and workforce teams. The posting states candidates must be located in Ohio. This is a supervisory/management role in customer care, not software engineering.

Sidecar Health, a mission-driven health insurance startup, is hiring a Senior SDET to join its Member Experience engineering team, where you'll own the quality engineering foundation for member-facing products including care navigation, benefits understanding, claims submission, and plan management. You'll design and maintain scalable test automation frameworks across web and mobile platforms, develop comprehensive regression suites, shift quality left by embedding with product teams, build CI/CD-integrated pipelines, and pioneer AI-powered quality engineering through LLM-assisted test generation and autonomous QA agents. Required experience includes significant hands-on SDET or test automation work with deep expertise building frameworks from scratch, strong programming skills (Java, Python, TypeScript), modern web testing (React/Next.js), API/integration testing, CI/CD integration, AWS cloud infrastructure knowledge, and excellent debugging abilities. The role offers competitive salary, bonus, equity, and comprehensive benefits at a fast-moving startup solving a meaningful healthcare problem. **Must be based in California**—this is a non-negotiable geographic requirement for the position.

A Vice President of Marketing role at Sidecar Health (health insurance, US-remote) leading B2B demand generation, ABM, paid media, content strategy, and marketing technology across broker, consultant, and employer segments. Requires proven experience building demand gen infrastructure from scratch, managing multimillion-dollar budgets, and running ABM at scale. This is a business/marketing function, not software engineering.

A Lead Product Manager, AI role at Sidecar Health (health insurance) owning AI-powered member experiences, agentic systems, intelligent assistants, and LLM-driven features to help members search for care and make informed healthcare decisions. Requires 5+ years product management, 2+ years AI product experience, and Bachelor's in CS/related field. **Must reside in California.** This is a product management function, not software engineering, and has a geographic restriction.

Head of Claim Operations at Sidecar Health leading multidisciplinary claims team across adjudication, quality, operations, and clinical programs. Focuses on AI/automation-driven claims transformation, operational scaling, and compliance rigor for growing membership. Fully remote role; requires health insurance claims leadership experience and proven track record with AI/automation implementation.