Associate Director, Market Strategy Advisory

This role sits within Oscar's Insurance Product Development team, working directly with market leadership to assess market dynamics, identify strategic opportunities, and build actionable plans across growth, retention, and portfolio performance. The position operates at the intersection of Insurance Product, Finance, Network, and Sales, translating complex data into executive-ready recommendations.

The successful candidate will develop business cases for market entry and portfolio optimisation, monitor performance trends across markets and segments, and transition approved strategies to market teams for execution. Strong cross-functional alignment and clear communication are central to the role, which reports to the Vice President of Insurance Product Innovation and Development.

• Develop and advance market strategies to improve growth, retention, and performance across Oscar's portfolio
• Analyse market dynamics, competitive positioning, and regulatory factors to inform market strategy decisions
• Build and contribute to business cases for new market entry, portfolio optimisation, and segment-specific opportunities
• Partner with Finance, Network, Sales, Marketing, Product, and Clinical stakeholders to align on recommendations
• Monitor performance trends across markets and segments, identifying optimisation and remediation opportunities
• Develop executive-ready materials and narratives to support leadership decision-making

• Bachelor's degree required
• 8 or more years of experience in healthcare, consulting, strategy, or ACA/IFP product roles
• Demonstrated experience in market analysis, performance evaluation, or growth strategy
• Experience developing business cases alongside market and product leadership
• Willingness to travel up to 25%
• Bonus: MBA, direct ACA or IFP market experience, or exposure to value-based care models

Oscar is a technology-driven health insurance company founded in 2012. Built on a full-stack technology platform, Oscar focuses on delivering a member-first experience, combining insurance products with digital tools and clinical support to make health care more accessible and navigable.