Senior Director, Strategic Finance & Enterprise Planning

The role

The Senior Director will lead the annual operating plan cycle and partner with leaders to translate priorities into financial plans. You will drive the strategic investment process by building business cases and supporting resource allocation.

What you will do

• Lead key components of the annual operating plan cycle
• Partner with business leaders to evaluate strategic investment opportunities
• Build financial models, business cases, and decision frameworks
• Develop clear reporting and insights on plan performance and investment progress
• Support executive discussions by synthesizing complex financial and operational inputs
• Identify opportunities to improve planning accuracy and resource allocation
• Compliance with all applicable laws and regulations
• Other duties as assigned

Required qualifications

• 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
• Strong project management skills
• High degree of ownership, and ability to balance strategic thinking with operational execution

Nice to have

• 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

Benefits

• medical, dental, and vision benefits
• 11 paid holidays
• paid sick time
• paid parental leave
• 401(k) plan participation
• life and disability insurance
• paid wellness time and reimbursements
• unlimited vacation program
• company equity grants

About the company

Oscar is a health insurance company built around a full stack technology platform. It was started in 2012 to create a health insurance company that behaves like a doctor in the family.