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Salary: USD 196,733 - 258,212 / annual
Oscar Health is seeking a Senior Director of Strategic Finance & Enterprise Planning to join its Strategic Finance team. Oscar is a technology-first health insurance company founded in 2012, built on a full-stack platform with a focus on member experience.
In this role, you will lead key components of the annual operating plan cycle, partnering with Finance, Strategy, and business leaders to translate company priorities into financial plans, targets, and investment decisions. You will drive the strategic investment process by building business cases, evaluating trade-offs, and supporting resource allocation toward the company's highest-priority initiatives. You will report to the VP, FP&A.
Key responsibilities include:
- Leading the annual operating plan cycle and partnering across Finance, Strategy, and business units to develop financial plans and targets
- Evaluating strategic investment opportunities, assessing trade-offs, and ensuring capital and operating resources align with company priorities
- Building financial models, business cases, and decision frameworks to support investment prioritization and ROI assessment
- Developing reporting and insights on plan performance, investment progress, risks, and opportunities for senior leadership
- Synthesizing complex financial and operational inputs into concise executive recommendations
- Identifying opportunities to improve planning accuracy, resource allocation, and investment discipline across the organization
The role is fully remote, with Dallas, TX as the associated hub office. Future work models may evolve to include hybrid presence at the hub.
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 cross-functional alignment
- 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)
