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 is a remote position, open to candidates who reside in: Dallas, TX. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $196,733 - $258,212 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.