Executive Strategy Director, CEO Office

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

Benefits offered by this job

Unlimited vacation

Equity grants

Annual performance bonuses

Benefits package

Job summary

Oscar Health is seeking a Director of Strategic Planning in the Office of the CEO to drive the company strategy across Corporate Strategy, Finance, Communications, and business teams. This leader will synthesize complex issues into executive-ready narratives and build planning architecture to scale with clarity.

You will report to the Vice President of Corporate Strategy and influence enterprise priorities with rigorous planning and accountable execution.

Qualifications

• 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 in fast-paced, high-growth, or highly regulated organizations.

Responsibilities

• Shape and manage the CEO operating agenda, ensuring executive forums focus on high-value 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 and support leadership decisions.
• Build business cases that quantify opportunities, surface investment needs, and clarify tradeoffs.
• Maintain visibility across critical priorities and escalate where needed.
• Serve as a trusted strategy partner to Corporate Strategy leadership and the CEO office on emerging priorities.
• Help strengthen Oscar's operating rhythm as the company scales with clarity and accountability.
• Comply with all applicable laws and regulations.
• Other duties as assigned.

Skills

Strategic planning

Executive storytelling

Cross-functional collaboration

Executive presentation

Operating cadence design

Education

MBA preferred

Job description

Oscar Health is seeking a Director of Strategic Planning in the Office of the CEO to drive the company strategy across Corporate Strategy, Finance, Communications, and business teams. This leader will synthesize complex issues into executive-ready narratives and build planning architecture to scale with clarity.

You will report to the Vice President of Corporate Strategy and influence enterprise priorities with rigorous planning and accountable execution.