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
- 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
- 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
- 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
- Summarize internal data, market intelligence, and competitive intelligence
- Develop executive ready materials and narratives to support rapid decision-making
- Contribute to a disciplined fact-based approach to market strategic efforts
- Compliance with all applicable laws and regulations
- Other duties as assigned
Requirements:
- Bachelor's Degree
- 8+ years of experience in healthcare, consulting, strategy, or ACA/IFP product roles
- Demonstrated experience in market analysis, performance evaluation, or growth strategy support
- Experience developing business cases and recommendations alongside market and product leadership
- Willingness to travel up to 25%.
Bonus points:
- Master of Business Administration or equivalent
- Direct experience within ACA, IFP, or adjacent healthcare markets
- Familiarity with market entry strategy, product portfolio optimization, or provider/network strategy development
- Experience supporting senior leadership decision-making processes
- Exposure to value-based care models, partnerships, or healthcare ecosystem strategy, focused on health insurance
This is an authentic Oscar Health job opportunity.
At Oscar, being an Equal Opportunity Employer means more than upholding discrimination-free hiring practices. It means that we cultivate an environment where people can be their most authentic selves and find both belonging and support. We're on a mission to change health care -- an experience made whole by our unique backgrounds and perspectives.
Pay Transparency: Final offer amounts, within the base pay set forth above, are determined by factors including your relevant skills, education, and experience. Full-time employees are eligible for benefits including: medical, dental, and vision benefits, 11 paid holidays, paid sick time, paid parental leave, 401(k) plan participation, life and disability insurance, and paid wellness time and reimbursements.
Artificial Intelligence (AI): Our AI Guidelines outline the acceptable use of artificial intelligence for candidates and detail how we use AI to support our recruiting efforts.
Reasonable Accommodation: Oscar applicants are considered solely based on their qualifications, without regard to applicant’s disability or need for accommodation. Any Oscar applicant who requires reasonable accommodations during the application process should contact the Oscar Benefits Team ([email protected]) to make the need for an accommodation known.
California Residents: For information about our collection, use, and disclosure of applicants’ personal information as well as applicants’ rights over their personal information, please see our Privacy Policy.
Skills Required
- Bachelor's degree
- 8+ years of experience in healthcare, consulting, strategy, or ACA/IFP product roles
- Experience in market analysis, performance evaluation, or growth strategy support
- Experience developing business cases and recommendations with market and product leadership
- Willingness to travel up to 25%
- Master of Business Administration or equivalent
- Direct experience within ACA, IFP, or adjacent healthcare markets
- Familiarity with market entry strategy, product portfolio optimization, or provider/network strategy development
- Experience supporting senior leadership decision-making processes
- Exposure to value-based care models, partnerships, or healthcare ecosystem strategy focused on health insurance
Oscar Health Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Oscar Health and has not been reviewed or approved by Oscar Health.
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Healthcare Strength — Employer-sponsored medical coverage for employees and their families with mental-health support is prominently offered. Wellness programming and digital care access add to perceived strength.
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Parental & Family Support — Paid parental leave of 10+ weeks, backup care, and family-forming support (including fertility and adoption benefits) are part of the package. Reproductive‑loss leave is also noted.
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Leave & Time Off Breadth — Multiple time‑off options, wellness days, and an unlimited vacation program for some roles are described. Paid holidays, paid sick time, and a long‑tenure sabbatical broaden time‑away choices.
Oscar Health Insights
What We Do
Oscar Health, Inc. (NYSE: OSCR) is a leading consumer health company that gives people power over their healthcare. Oscar Health serves millions of consumers, employers, brokers, and partners through Oscar Insurance, Lucie Health Marketplace, and Trove Group. Together these businesses deliver exceptional lifestyle products and technology platforms that make healthcare easy to choose, use, and experience.
