Director of Strategic Planning

Who you are

• 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
• MBA or equivalent graduate business training preferred; recent MBA graduates with relevant strategy experience are encouraged
• Healthcare, insurance, technology, or regulated industry experience preferred

What the job involves

• 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
• 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