Oscar is an AI operations analyst that watches every location 24/7, catching revenue leaks, labor inefficiencies, and compliance risks, then delivering the alerts, reports, and action plans your team needs to fix them fast. Backed by Techstars.
About the role
The Senior Director of Strategic Finance & Enterprise role will help lead the annual operating plan cycle, partnering with Finance, Strategy, and business leaders to translate company priorities into financial plans, targets, and executive-ready materials. You will also drive the strategic investment process by building business cases, evaluating trade-offs, and supporting resource allocation toward the company's highest-priority initiatives.
What they're looking for
- 12+ years of experience in finance, FP&A, corporate strategy, investment banking, consulting, or a related strategic finance role
- Experience leading or supporting annual planning, budgeting, forecasting, long-range planning, or capital allocation processes
- Strong financial modeling, analytical, and business case development skills
- Influence senior stakeholders and drive alignment across cross-functional teams
- Excellent communication skills, with the ability to turn analysis into clear executive-level recommendations
- Strong project management skills and comfort operating in complex, fast-paced environments
More about this role
Hi, we're Oscar. We're hiring a Senior Director, Strategic Finance and Enterprise Planning to join our Strategic Finance team.
Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.
The Senior Director of Strategic Finance & Enterprise role will help lead the annual operating plan cycle, partnering with Finance, Strategy, and business leaders to translate company priorities into financial plans, targets, and executive-ready materials. You will also drive the strategic investment process by building business cases, evaluating trade-offs, and supporting resource allocation toward the company's highest-priority initiatives. You bring FP&A or strategic finance experience, excellent financial modeling and the judgment to influence senior stakeholders.
You will report into the VP, FP&A.
Work Location: This position is based in our New York City office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day...
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