Director, Commercial Strategy

Our healthcare system is the leading cause of personal bankruptcy in the U.S. Every year, over 50 million Americans suffer adverse financial consequences as a result of seeking care, from lower credit scores to garnished wages. The challenge is only getting worse, as high deductible health plans are the fastest growing plan design in the U.S. Cedar’s mission is to leverage data science, smart product design and personalization to make healthcare more affordable and accessible. Today, healthcare providers still engage with its consumers in a “one-size-fits-all” approach; and Cedar is excited to leverage consumer best practices to deliver a superior experience.The Role  Cedar is looking for a Director, Commercial Strategy to help strengthen how we evaluate, prioritize, and scale our product investments across Cedar’s portfolio. This role will sit within Cedar’s Commercial Strategy & GTM team and partner closely with Product, Finance, Sales, Client Management, Delivery, and Product Marketing. The role will bring structure and analytical rigor to Cedar’s product investment decisions, helping connect market signals, product strategy, business cases, unit economics, and commercial outcomes around new and emerging products. This is a high-impact role for someone who enjoys turning ambiguity into clear recommendations, building executive-ready business cases, and helping a company make sharper decisions about where to invest, scale, pause, or deprioritize. Responsibilities Commercial Strategy & Portfolio Planning Support Cedar’s product and commercial strategy across core products and emerging growth bets, including AI offerings. Build and maintain frameworks for evaluating product investments across market opportunity, customer need, revenue potential, margin impact, strategic fit, and feasibility. Partner with Product on portfolio prioritization, roadmap tradeoffs with commercial implications, and investment recommendations. Synthesize customer, market, sales, competitive, and product performance signals into clear recommendations for Commercial and Product leadership. Identify where Cedar may be over- or under-investing across products, segments, or growth opportunities. Business Cases & Product Economics Build and pressure-test business cases for new product bets, product extensions, and strategic initiatives. Develop financial and operating models to evaluate revenue opportunity, gross margin, implementation effort, cost to serve, unit economics, and ROI. Partner with Finance to align on assumptions, reporting, and product-level business performance. Support pricing, packaging, and monetization analysis in partnership with Commercial Strategy, Finance, Product, and Sales. Help define success metrics and stage gates for product investments, pilots, and commercialization efforts. Executive Decision Support Prepare investment memos, portfolio reviews, and executive-ready materials for Commercial leadership, Product leadership, ELT, ...