Senior Director, Strategic Finance & Enterprise Planning
Oscar Health • New York, NY3d • $218,592 - $286,902 • Hybrid
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Senior Director, Strategic Finance & Enterprise Planning
Oscar Health•New York, NY
•$218,592 - $286,902•Hybrid
About The Position
Oscar is hiring a Senior Director of Strategic Finance & Enterprise Planning to join its Strategic Finance team. The role helps 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. It also drives the strategic investment process by developing business cases, evaluating trade-offs, and supporting resource allocation toward the company’s highest-priority initiatives. The successful candidate brings FP&A or strategic finance experience, strong financial modeling skills, and the judgment to influence senior stakeholders. The role reports to the VP, FP&A. It is based in Oscar’s New York City office and follows a hybrid schedule with three in-office days each week. Thursday is required for team meetings and events; the other two office days are flexible. The base pay range is $218,592–$286,902 per year. The position is also eligible for employee benefits, participation in Oscar’s unlimited vacation program, company equity grants, and annual performance bonuses.
Requirements
- 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.
- Ability to influence senior stakeholders and drive alignment across cross-functional teams.
- Excellent communication skills, including the ability to turn analysis into clear executive-level recommendations.
- Strong project management skills and comfort operating in complex, fast-paced environments.
- High degree of ownership and ability to balance strategic thinking with operational execution.
Nice To Haves
- Experience in similar roles in strategy consulting, financial services, or insurance industries, such as private equity, venture capital, or investment banking.
- Strong preference for healthcare industry experience and deep market knowledge.
- Advanced degree or professional designation, such as an MBA or CFA.
Responsibilities
- 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.
- Partner with business leaders to evaluate strategic investment opportunities, assess trade-offs, and ensure capital and operating resources are allocated to the company’s highest-priority initiatives.
- Build financial models, business cases, and decision frameworks to support investment prioritization, ROI assessment, and long-range value creation.
- Develop reporting and insights on plan performance, investment progress, risks, and opportunities for senior leadership.
- Support executive discussions by synthesizing complex financial and operational inputs into concise recommendations.
- Identify opportunities to improve planning accuracy, resource allocation, and investment discipline across the organization.
- Comply with all applicable laws and regulations.
- Perform other duties as assigned.
Benefits
- Unlimited vacation program
- Company equity grants
- Annual performance bonuses
- Medical benefits
- Dental benefits
- Vision benefits
- 11 paid holidays
- Paid sick time
- Paid parental leave
- 401(k) plan participation
- Life insurance
- Disability insurance
- Paid wellness time and reimbursements
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What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
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