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Salary: USD 196,733 - 258,212 / annual
Oscar Health is seeking a Senior Director of Strategic Finance & Enterprise Planning to lead key components of the annual operating plan cycle and drive strategic investment processes. You will partner with Finance, Strategy, and business leaders to translate company priorities into financial plans, targets, and executive-ready materials. This role reports to the VP, FP&A.
Key responsibilities include:
- Lead the annual operating plan cycle, partnering across Finance, Strategy, and business units to develop financial plans, targets, and investment decisions
- Evaluate strategic investment opportunities, assess trade-offs, and ensure capital and operating resources align with the company's highest-priority initiatives
- Build financial models, business cases, and decision frameworks to support investment prioritization and ROI assessment
- Develop clear reporting and insights on plan performance, investment progress, risks, and opportunities for senior leadership
- Synthesize complex financial and operational inputs into concise executive recommendations
- Identify opportunities to improve planning accuracy, resource allocation, and investment discipline across the organization
Oscar is the first health insurance company built around a full-stack technology platform with a relentless focus on serving members. Founded in 2012, Oscar combines healthcare delivery with technology innovation.
Requirements:
- 12+ years of experience in finance, FP&A, corporate strategy, investment banking, consulting, or related strategic finance roles
- Experience leading or supporting annual planning, budgeting, forecasting, long-range planning, or capital allocation processes
- Strong financial modeling, analytical, and business case development skills
- Ability to influence senior stakeholders and drive alignment across cross-functional teams
- Excellent communication skills with ability to translate analysis into clear executive-level recommendations
- Strong project management skills and comfort in complex, fast-paced environments
- High degree of ownership and ability to balance strategic thinking with operational execution
Bonus qualifications:
- Experience in strategy consulting, financial services, or insurance industries (private equity, venture capital, investment banking)
- Healthcare industry experience and deep market knowledge
- Advanced degrees or professional designations (MBA, CFA)
