Top Tech Jobs & Startup Jobs in Boston, MA

The Director of Underwriting will lead and develop the underwriting team, personally handle complex cases, establish guidelines, and partner with Sales for new business growth.

This role involves scaling broker growth strategy by building relationships, meeting sales goals, and refining market strategies while representing Sidecar Health.

The Regional Sales Manager will lead broker growth strategy, build relationships, exceed sales goals, and enhance market presence within the healthcare sector.

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.