The Head of Enterprise Sales will lead the sales strategy, drive growth, secure national client accounts, and collaborate with internal teams at Sidecar Health.

As Lead Product Manager, you will drive product strategy and execution for member-facing healthcare solutions, collaborating with cross-functional teams to enhance user experience and promote growth.

The Director of Account Management leads the team, manages client relationships, drives operational efficiency, and oversees growth targets in health insurance.

Lead and own actuarial and financial analytics for pricing, forecasting, product development, and experience studies. Build and maintain financial models, perform deep-dive cost and risk analyses, present recommendations to leadership, mentor junior analysts, and implement AI-driven approaches to improve actuarial processes.

Design, build, and operate production-grade LLM systems and multi-agent AI workflows. Own prompt architecture, RAG pipelines, cloud-native AI infrastructure, monitoring, and reliability to deliver scalable member-facing and operational solutions.

As the Lead Product Designer, you will define and execute the member and provider experience strategy, leading cross-functional initiatives and creating scalable, user-friendly design solutions across mobile and web platforms.