Jobs at Sidecar Health

You will own enterprise sales strategy and execution, driving new business growth and managing national accounts at a pivotal moment for the company. Reporting to the CEO, you will set revenue targets, build a repeatable sales process, and strengthen relationships with brokers and enterprise clients.

You'll lead the B2B growth engine for a mission-driven health insurance company transforming healthcare affordability. You'll own **demand generation**, **ABM strategy**, and **multimillion-dollar media budgets**, reporting to the CMO.

You'll own the quality engineering foundation for member-facing products at Sidecar Health, building automation frameworks and integrating AI-powered testing to ensure reliable releases. You'll work with product engineering squads to shift quality left and pioneer **AI-assisted test generation** and **autonomous QA agents**.

You'll own **AI-powered member experiences** that transform how people shop for healthcare. You'll drive strategy from zero to one, design **human-in-the-loop workflows**, and balance user trust with technical feasibility. This role offers the chance to redefine health insurance at a mission-driven startup.

You'll accurately review and enter medical claims for a **mission-driven health insurance startup**. Your core impact is ensuring members get timely, accurate claim resolution. This role stands out for its **clear growth pathways** into data operations and analytics. You'll work in a **fast-paced, metrics-driven environment** with a supportive remote team.

You'll lead and grow our Account Management organization, balancing client relationships with building scalable processes and systems. You'll drive retention and expansion across employer groups while partnering cross-functionally. This role is ideal for someone who thrives in client-facing environments and is equally energized by operational infrastructure.

You'll lead **quality strategy** and **AI-powered quality tools** at a health insurance startup. Your work will directly impact **member experience** and **operational excellence**.

You'll own complex backend systems that power Sidecar Health's platform, designing and building scalable services and APIs. Your work directly impacts healthcare affordability and accessibility. You'll integrate **AI tools** into your daily workflow and make **architectural decisions** that ensure reliability at scale.

You'll own the full product experience at a mission-driven health insurance startup, building APIs and member-facing UIs. Your work will make **healthcare more accessible** for a growing user base. You'll integrate **AI tools daily** as a core part of how you build.

You'll own the **full training lifecycle** for Sidecar Health's operations teams, from program design to delivery. Your work directly shapes team readiness and confidence to deliver an **outstanding member experience**. This role offers hands-on ownership across content creation, facilitation, and continuous improvement.

You'll support members on their healthcare journeys by answering questions and solving problems as part of a mission-driven team. You'll act as in-person support for client groups in Ohio, building relationships and ensuring excellent service. This high-visibility role offers opportunities for professional development and collaboration across teams.

You'll own and scale claims operations for a **tech-enabled health insurance company** redefining healthcare access. You'll lead a multidisciplinary team, shape the **AI automation roadmap**, and drive operational excellence at a high-growth inflection point. This role offers the chance to transform a broken system and make healthcare affordable.