Senior Director, Markets Strategic Advisory & Intelligence

About this role

Hi, we're Oscar. We're hiring a Senior Director, Markets Strategic Advisory & Intelligence 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 Senior Director, Markets Strategic Advisory & Intelligence leads market-specific strategy development across Oscar's service areas. You will own the enterprise market intelligence and strategic insight function that serves as the single source of truth for product strategy, portfolio design, market expansion, and investment decisions. You will own the development of integrated intelligence capabilities spanning consumer research, competitor intelligence, market analytics and performance insights to ensure data-driven decision-making across our product portfolio.

Working cross-functionally across product, network, clinical, sales, growth, and market leadership, this leader develops actionable strategies related to market expansion (MSA and new geography), product positioning, portfolio optimization, and segment-specific opportunities. You will serve as a strategic advisor to executive and market level leadership, translating market insights and performance data into clear recommendations that support market-level decision-making.

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: $218,592.00- $286,902.00 per year. The base pay for this role in all other locations is:: $196,732- $258,211 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program company equity grants and annual performance bonuses.

Responsibilities:

• Market Strategy & Intelligence

• Lead market-specific strategic advisory functions across our service areas

• Oversee market research, competitive intelligence, and performance analytics of product portfolio specific dynamics to clarify growth and optimization opportunities

• Develop market and product specific right to win strategies informed by competitive, regulatory, and consumer trends

• Translate complex analyses into executive-ready recommendations and strategic insights

Portfolio Strategy & Market Expansion

• Lead portfolio performance assessments and identify remediation and growth opportunities

• Support recommendations related to product positioning, market alignment, and portfolio investments (vendors, network, partnerships)

• Oversee analyses supporting market expansion, strategic partnerships, and new product or growth opportunities

Strategic Leadership & Execution

• Be a strategic advisor to executive and market leadership teams

• Lead cross-functional strategic programs and planning efforts

• Facilitate strategic planning sessions alongside corporate strategy and finance, overseeing development of executive presentations and strategic materials

Team Leadership

• Lead strategy, intelligence, and analytics team members

• Build partnerships with product, finance, sales, clinical, network, actuarial, and market leadership

• Foster analytical rigor, collaboration, and disciplined decision-making

• Compliance with all applicable laws and regulations

• Other duties as assigned

Requirements:

• Bachelor's degree.

• 12+ years experience in healthcare strategy, insurance product strategy, consulting, or strategic planning

• 6+ years people leadership experience managing multi-level teams

• Expertise in ACA individual and small group QHP markets

• Background in market analytics, competitor intelligence, and business case development

Bonus points:

• MBA, MHA, MPH or related advanced degree

• Experience in internal strategy or consulting functions

• Familiarity with ACA market dynamics and healthcare competitive landscapes

• Experience supporting market expansion and healthcare partnership strategies

• Willingness to drive to outcomes, work with large datasets and distill analyses into actionable business insights with a structured and systematic thought process

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