Director, Strategic Planning — CEO Office

Oscar Health; New York (NY); Hybrid; USD 199,000 - 261,000; Full time

Benefits offered by this job

Medical

Dental

Vision

11 paid holidays

Paid sick time

Paid parental leave

401(k) plan participation

Life and disability insurance

Equity grants

Job summary

Oscar Health is seeking a Director, Strategic Planning, Office of CEO to help develop and execute the company’s strategy. You will partner with the CEO office, executive leadership, Finance, Communications, People, and business teams to connect enterprise priorities with leadership decision-making and execution.

You will report into the Vice President, Corporate Strategy. The role is based in New York with a hybrid schedule requiring 3 in-office days per week, including Thursdays for team

Qualifications

• 10+ years of experience in strategy, business operations, corporate planning, chief of staff, or related roles.
• 8+ years developing executive presentations, board materials, strategic recommendations or business cases for senior leadership.
• 6+ years supporting executive leadership, corporate strategy, business operations, or enterprise planning initiatives.

Responsibilities

• Shape and manage the CEO operating agenda with a focus on high-value priorities.
• Translate CEO priorities into clear strategic narratives and ownership models.
• Develop executive-ready materials that clarify complex topics and support decisions.
• Build business cases quantifying opportunities and investment needs.
• Maintain visibility across critical priorities and ensure escalation when needed.
• Serve as a trusted strategy partner to Corporate Strategy leadership and the CEO office.
• Help strengthen Oscar's operating rhythm with clarity and disciplined execution.
• Compliance with laws and regulations.
• Other duties as assigned.

Skills

Strategic planning

Cross-functional collaboration

Executive communication

Storytelling & narratives

Education

MBA

Job description

Oscar Health is seeking a Director, Strategic Planning, Office of CEO to help develop and execute the company’s strategy. You will partner with the CEO office, executive leadership, Finance, Communications, People, and business teams to connect enterprise priorities with leadership decision-making and execution.

You will report into the Vice President, Corporate Strategy. The role is based in New York with a hybrid schedule requiring 3 in-office days per week, including Thursdays for team