Associate Director, Market Strategy Advisory

Hi, we're Oscar. We're hiring an Associate Director, Market Strategy Advisory to join our Insurance Product Development team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Associate Director, Market Strategy Advisory develops and advances market strategies that improve growth, performance, and expansion across Oscar's portfolio. You will work directly with market leadership and partners to assess market dynamics, identify opportunities, and build relevant strategies to improve performance and unlock new growth. You will lead analyses and support development of business cases for market expansion, portfolio optimization, strategic partnerships, and segment-specific opportunities.

Operating at the center of Insurance Product, Finance, Network, and Sales, you will translate complex data into clear recommendations and help shape decisions on where and how the business competes and grows. The person in this role develops strategies and transitions them to market teams for execution, requiring strong alignment, clarity, and follow-through.

You will report into the Vice President, Insurance Product Innovation and Development.

Work Location: This is a remote / work-from-home role. You must reside in one of the following states: Arizona, California, Colorado, Florida, Georgia, Illinois, Massachusetts, Michigan, Nevada, New Jersey, New York, North Carolina, Ohio, Pennsylvania, Texas, or Virginia. Note, this list of states is subject to change. #LI-Remote

Pay Transparency: The base pay for this role in the states of California, Connecticut, New Jersey, New York, and Washington is: $163,944- $215,177 per year. The base pay for this role in all other locations is: $147,550- $193,659 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, and annual performance bonuses.

Responsibilities:

Market Strategy Advisory

• Support development of market strategies to achieve growth, retention, and performance improvement

• Analyze market dynamics, competitive positioning, and regulatory factors to inform right to win strategies (product, network, market share)

• Partner with market leaders to prioritize opportunities and refine local strategic plans, as part of our multi-year strategy development effort

Market Expansion & Entry

• Conduct analysis to support new market entry and expansion opportunities based on product receptivity, market sizing, competitor landscape, and regulatory considerations

• Contribute to development of business cases in partnership with corporate finance, sales, growth, network, and market leadership

• Support leadership decision-making with clear, data-driven insights

Portfolio Optimization & Performance

• Analyze product and market performance to identify optimization and remediation opportunities related to product offerings

• Support recommendations on portfolio changes, including plan positioning and market or demographic specific adjustments

• Monitor important performance trends across markets and segments served, alongside market leadership

Strategic Partnership & Innovation Support

• Analyze opportunities across important member segments, while supporting development of segment- strategies and growth opportunities

• Partner with finance, network, sales, marketing, product, and clinical to agree on opportunities and recommendations

• Translate complex analyses into clear, relevant insights for partners, while supporting transition of approved strategies for market leadership to implement

Insight Generation & Decision Support

• Summarize internal data, market intelligence, and competitive intelligence

• Develop executive ready materials and narratives to...