Overview

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.

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.