Head of Health Plans

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. #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

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; 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

Bachelor’s degree or commensurate 4 years of experience

5+ years experience collaborating and influencing at the executive level

Bonus points

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

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)
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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 (View email address on click.appcast.io Residents
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