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Salary: USD 198,720 - 260,820 / annual
Oscar Health is seeking a Director of Strategic Planning to join the Office of the CEO and Corporate Strategy team. This role sits at the intersection of executive leadership and enterprise operations, supporting the development and execution of company strategy across the organization.
You will partner with the CEO office, executive leadership, Finance, Communications, People, and business teams to translate enterprise priorities into clear strategic narratives, decision frameworks, and accountable execution plans. Key responsibilities include shaping the CEO operating agenda and ensuring executive forums focus on highest-value strategic and operational priorities; developing executive-ready materials that clarify complex topics and support high-quality leadership decisions; building business cases that quantify opportunities and surface investment needs; maintaining visibility across critical company priorities and identifying where additional structure or escalation is needed; and serving as a trusted strategy partner on emerging priorities and special projects.
You will report to the Vice President of Corporate Strategy. The role requires designing or improving strategic planning processes, operating cadences, and governance frameworks as Oscar scales. You'll work with complex, cross-functional initiatives involving multiple stakeholders and competing priorities in a fast-paced, highly regulated environment.
This is a hybrid position based in New York, requiring 3 days in-office per week with Thursdays as a mandatory in-office day for team meetings and events. The other two office days are flexible.
Required qualifications include 10+ years in strategy, business operations, corporate planning, or chief of staff roles; 8+ years developing executive presentations, board materials, and strategic recommendations; 6+ years supporting executive leadership in cross-functional environments; demonstrated experience designing strategic planning processes and operating models; 6+ years leading complex cross-functional initiatives; and 4+ years partnering with senior executives on strategic initiatives and business transformation. Experience in fast-paced, high-growth, or highly regulated organizations is essential.
Bonus qualifications include an MBA or equivalent graduate business training, and experience in healthcare, insurance, technology, or regulated industries.
