RemoteFull timeMid level$199k – $261kPosted today
Apply with JobAssistAbout 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
- 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- 6+ years of experience supporting executive leadership, corporate strategy, business operations, or enterprise planning initiatives in a cross-functional environment
- 4+ years of experience partnering with senior executives to drive strategic initiatives, organizational planning, or business transformation efforts
- 6+ years of experience leading complex, cross-functional initiatives involving multiple stakeholders and competing priorities
- 10+ years of experience in strategy, business operations, corporate planning, chief of staff, or related roles
- Demonstrated experience designing or improving strategic planning processes, operating cadences, governance frameworks, or cross-functional operating models
- 8+ years of experience developing executive presentations, board materials, strategic recommendations, or business cases for senior leadership
- 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
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