SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.
Salary: USD 218,592 - 286,902 / annual
Oscar Health is seeking a Senior Director of Strategic Finance & Enterprise Planning to join its Strategic Finance team. Oscar is a technology-enabled health insurance company founded in 2012, built around a full-stack platform with a focus on member-centric service.
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 develop clear reporting and insights on plan performance, investment progress, risks, and opportunities for senior leadership, and support executive discussions by synthesizing complex financial and operational inputs into concise recommendations.
Key responsibilities include:
- Leading the annual operating plan cycle in partnership with Finance, Strategy, and business leaders
- Evaluating strategic investment opportunities and ensuring capital and operating resources are allocated to highest-priority initiatives
- 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
- Supporting executive discussions with synthesized financial and operational recommendations
- Identifying opportunities to improve planning accuracy, resource allocation, and investment discipline
You will report to the VP, FP&A. The position is based in the New York City office with a hybrid work schedule requiring 3 days in-office per week. Thursdays are mandatory in-office for team meetings and events; the other two office days are flexible.
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)
