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:
- Shape and manage the CEO operating agenda, ensuring executive forums are focused on the highest-value strategic, operational, and organizational priorities.
- Partner with senior leaders to translate CEO priorities into clear strategic narratives, decision points, ownership models, and follow-through.
- Develop executive-ready materials that clarify complex topics, elevate key tradeoffs, and support high-quality leadership decisions.
- Build business cases that quantify opportunities, surface investment needs, clarify tradeoffs, and support executive decision-making.
- Maintain visibility across critical company priorities and identify where additional structure, escalation, or executive alignment is needed.
- Serve as a trusted strategy partner to Corporate Strategy leadership and the CEO office on emerging priorities, special projects, and enterprise planning moments.
- Help strengthen Oscar's operating rhythm as the company scales, with a focus on clarity, accountability, and disciplined execution.
- Compliance with all applicable laws and regulations.
- Other duties as assigned.
Requirements:
- 10+ years of experience in strategy, business operations, corporate planning, chief of staff, or related roles.
- 8+ years of experience developing executive presentations, board materials, strategic recommendations, or business cases for senior leadership.
- 6+ years of experience supporting executive leadership, corporate strategy, business operations, or enterprise planning initiatives in a cross-functional environment.
- Demonstrated experience designing or improving strategic planning processes, operating cadences, governance frameworks, or cross-functional operating models.
- 6+ years of experience leading complex, cross-functional initiatives involving multiple stakeholders and competing priorities.
- 4+ years of experience partnering with senior executives to drive strategic initiatives, organizational planning, or business transformation efforts.
- Experience working in fast-paced, high-growth, or highly regulated organizations where priorities frequently evolve.
Bonus points
- MBA or equivalent graduate business training preferred; recent MBA graduates with relevant strategy experience are encouraged.
- Healthcare, insurance, technology, or regulated industry experience preferred.
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.
Skills Required
- 10+ years of experience in strategy, business operations, corporate planning, chief of staff, or related roles
- 8+ years of experience developing executive presentations, board materials, strategic recommendations, or business cases for senior leadership
- 6+ years of experience supporting executive leadership, corporate strategy, business operations, or enterprise planning initiatives in a cross-functional environment
- Experience designing or improving strategic planning processes, operating cadences, governance frameworks, or cross-functional operating models
- 6+ years of experience leading complex, cross-functional initiatives involving multiple stakeholders and competing priorities
- 4+ years of experience partnering with senior executives to drive strategic initiatives, organizational planning, or business transformation efforts
- Experience working in fast-paced, high-growth, or highly regulated organizations where priorities frequently evolve
- MBA or equivalent graduate business training
- Healthcare, insurance, technology, or regulated industry experience
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
Health care is broken; we're trying to fix it. The Oscar team is focused on utilizing technology, design and data to humanize health care. We're a group of technology and health care professionals who looked at the current state of the US health care system, got frustrated by the horrible consumer experience, and decided to do something big about it. Backed by a renowned set of investors and advisors, we’ve set out to revolutionize health care.
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