Director, Corporate Strategy

Hi, we’re Oscar. We’re hiring a Director to join our Corporate Strategy 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.

The Director, Corporate Strategy supports the company in shaping Oscar’s corporate strategy, determining the course the company will take to maximize enterprise value and growth in a way that is aligned with the mission of the company. This leader supports the development of the company’s long‑term strategy by evaluating and executing strategic projects, deriving insights from external and internal research, and developing recommendations and scenarios for our executive team.

You will report into the Senior Director, Corporate Strategy.

This position is based in our New York City office, requiring a hybrid work schedule with 3 days of in‑office work per week. Thursdays are a required in‑office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

The base pay for this role is: $198,720 – $260,820 per year. You are also eligible for employee benefits, participation in Oscar’s unlimited vacation program, company equity grants, and annual performance bonuses.

• In partnership with the Senior Director of Corporate Strategy and Oscar’s executive team, shape the corporate strategy of Oscar
• Manage the day‑to‑day partnership strategies with internal and external stakeholders
• Support the execution of multiple simultaneous strategy projects, which will be surfaced to the executive team and the board
• Collaborate with SMEs and leaders across the organization
• Maintain a strong external orientation, leveraging deep healthcare industry and market knowledge, a pulse on healthcare investments and innovation, as well as insights into our competition and our customers’ needs to bring together research and strategic decisions in key areas
• Develop thorough and analytical business cases, including economic modeling, scenario development, risks, trade‑off evaluation, and prioritization decisions – tying opportunities back to Oscar and our differentiation to ensure we appropriately assess our right to win
• Communicate the established corporate strategy to the organization in partnership with our Communications and leadership team; drive change management as needed
• Assemble and maintain a foundation of intelligence – e.g., business financials / competitive data – that can serve as a fact base for projects and discussions
• Compliance with all applicable laws and regulations
• Other duties as assigned

• Bachelor’s degree or commensurate 4 years of experience
• 10+ years experience, with 7+ of those years in healthcare consulting or a strategic role with a health payer
• 5+ years experience collaborating and influencing at the executive level

• Master’s degree from top‑tier program in business, health administration, or related field

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.

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.

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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 () to make the need for an accommodation known.

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