Senior Director, Strategic Finance & Enterprise Planning

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.

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. 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 for team meetings and events, while your other two office days are flexible to suit your schedule.

Pay Transparency: The base pay for this role is: $218,592 - $286,902 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and annual performance bonuses.

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 against 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 clear 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.
• Compliance with all applicable laws and regulations
• Other duties as assigned

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.
• 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.
• High degree of ownership, and ability to balance strategic thinking with operational execution.

Bonus points:

• Experience in similar roles in strategy consulting, financial services, or insurance industries (ex: private equity, venture capital, investment banking)
• Strong preference for healthcare industry experience and deep market knowledge.
• Advanced degrees or professional designations, such as an MBA or CFA.

This is an authentic Oscar Health job opportunity.

At Oscar, being an Equal Opportunity Employer means more than upholding discrimination-free hiring practices. It means that we cultivate an environment where people can be their most authentic selves and find both belonging and support. We're on a mission to change health care -- an experience made whole by our unique backgrounds and perspectives.

Pay Transparency: Final offer amounts, within the base pay set forth above, are determined by factors including your relevant skills, education, and experience. Full-time employees are eligible for benefits including: medical, dental, and vision benefits, 11 paid holidays, paid sick time, paid parental leave, 401(k) plan participation, life and disability insurance, and paid wellness time and reimbursements.

Artificial Intelligence (AI): Our AI Guidelines outline the acceptable use of artificial intelligence for candidates and detail how we use AI to support our recruiting efforts.

Reasonable Accommodation: Oscar applicants are considered solely based on their qualifications, without regard to applicant’s disability or need for accommodation. Any Oscar applicant who requires reasonable accommodations during the application process should contact the Oscar Benefits Team (accommodations@hioscar.com) to make the need for an accommodation known.

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