Director, Commercial Strategy

About this role

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, and board-facing discussions.

• Track product impact against agreed business outcomes, including revenue, retention, adoption, margin, implementation readiness, and customer value.

• Support build / buy / partner analysis, including strategic rationale, partnership economics, and commercial implications.

• Help create a repeatable operating model for product investment tracking and ROI review.

Requirements

• 6-10+ years of experience in strategy, business operations, strategic finance, consulting, product strategy, GTM strategy, or a related role.

• Experience in B2B SaaS, healthcare technology, fintech, revenue cycle, or another complex enterprise software environment strongly preferred.

• Strong financial modeling and analytical skills, with the ability to translate data into clear business recommendations.

• Experience building business cases, investment recommendations, market analyses, or product / segment prioritization frameworks.

• Strong executive communication skills and comfort preparing materials for senior leadership.

• Ability to work cross-functionally with Product, Finance, Sales, Product Marketing, Client Management, Delivery, and Operations.

• Comfort operating in ambiguity and creating structure around complex, early-stage product and market questions.

• Strong judgment, intellectual honesty, and ability to recommend when Cedar should invest, pause, pivot, or deprioritize.

What Success Looks like

• Cedar has clearer business cases and investment criteria for major product bets.

• Commercial, Product, Finance, and PS&O are aligned on how product investments are evaluated and tracked.

• ELT has better visibility into product-level business performance and ROI.

• Cedar makes sharper decisions about where to invest, scale, pause, or deprioritize.

• The Commercial Strategy & GTM team has strong…