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Senior Director, Corporate Strategy - job 1 of 2

Hi, we're Oscar. We're hiring a Senior Director, Corporate Strategy 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.

 

About the role:

As a Senior Director, Corporate Strategy, you will play a critical role 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. As a high-performing leader, you will shape the long-term strategy of the company by leading and executing large-scale cross-functional strategic initiatives critical to Oscar’s strategic and operational plans. You will work closely with senior executives across the organization to enhance Oscar’s competitive position and drive growth.

You will report into the Vice President, Corporate Strategy.

Work Location: 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

Pay Transparency: The base pay for this role is: $232,000 - $304,500 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and annual performance bonuses.

 

Responsibilities:

  • Shape the corporate strategy of Oscar in partnership with the executive team.
  • Evaluate and execute strategic projects, deriving insights from external and internal research, and develop recommendations and scenarios for Oscar’s executive team.
  • Develop thorough and analytical business cases, including economic modeling, scenario development, risks, trade-off evaluation, and prioritization decisions.
  • Develop key performance indicators and metrics to evaluate the success of strategic initiatives and projects.
  • Serve as the dedicated corporate strategy lead for Oscar’s shared services functions.
  • Collaborate deeply 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.
  • 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. 

Requirements:

  • A bachelor's degree or commensurate 4 years of experience.
  • 12+ years experience, with 10+ of those years in healthcare consulting or a strategic role in the healthcare industry.
  • 7+ years experience collaborating and influencing at the executive level.
  • 5+ years experience defining and deploying strategies for organizations at the company level.

Bonus points:

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

This is an authentic Oscar Health job opportunity. Learn more about how you can safeguard yourself from recruitment fraud here

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.

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CEO of Oscar Health
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Mark Bertolini
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Average salary estimate

$268250 / YEARLY (est.)
min
max
$232000K
$304500K

If an employer mentions a salary or salary range on their job, we display it as an "Employer Estimate". If a job has no salary data, Rise displays an estimate if available.

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Oscar Health is an American health insurance company headquartered in New York City. Through telemedicine, healthcare-focused technology interfaces, and clear claims pricing systems, the company focuses on the health insurance market.

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Full-time, hybrid
DATE POSTED
November 27, 2025
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