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Director, Strategic Planning, Office of the CEO

Oscar Health

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This role on the market

5,897 open director roles across 556 companies are on ApplySarthi right now, most of them in Bengaluru (109), Hyderabad (59), Mumbai (42).

What director roles keep asking for: Stakeholder management (12%) — counted across their open postings here.

Oscar Health has 280 open roles listed here.

Counted across 14 company job boards, updated as roles open and close.

Preparing for this interview

Interviews for director roles keep coming back to Stakeholder management. Practise those questions before you sit with Oscar Health.

Questions you are likely to be asked

  1. Why do you want to join Oscar Health?
  2. What is a weakness you are working on, and how?
  3. Tell me about yourself, and why this role is the right next step.
  4. Tell me about a problem you solved at work that you are proud of.
  5. Tell me about a time you disagreed with your manager. What happened?

Prep Sarthi gives you a free mock interview: an AI interviewer asks you questions like these out loud, from your own CV and this job, and shows your score and your weakest answer.

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Hi, we're Oscar. We're hiring a Director, Strategic Planning, Office of CEO to join our Strategic Planning 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:

Oscar is seeking a Director, Strategic Planning, Office of CEO to help support the development and execution of the company's strategy. Sitting within Corporate Strategy, this leader will partner across the CEO office, executive leadership, Finance, Communications, People, and business teams to connect enterprise priorities with leadership decision-making and accountable execution. This role requires a strong strategy operator who can synthesize complex issues, create executive-ready narratives, and build the planning architecture that helps Oscar scale with clarity.

You will report into the Vice President, Corporate Strategy.

Work Location: This position is based in our New York, NY 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: $ $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

Responsibilities:

Requirements:

Bonus points

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 (accommodations@hioscar.com) 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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Listed on greenhouse · posted 2026-08-26. ApplySarthi collects openings and links to application pages; the role is advertised by Oscar Health, not by us.