Remote: Strategic Finance & Enterprise Planning Leader

Oscar Health; Dallas (TX); Remote; USD 197,000 - 258,000; Full time

Benefits offered by this job

Medical, dental, vision benefits

11 paid holidays

Paid sick time

Paid parental leave

401(k) plan participation

Life and disability insurance

Paid wellness time and reimbursements

Job summary

Oscar Health seeks a Senior Director, Strategic Finance and Enterprise Planning to lead the annual operating plan cycle and translate priorities into financial plans and executive-ready materials.

You will build business cases, evaluate trade-offs, and guide resource allocation toward top initiatives, leveraging FP&A experience and strong modeling to influence senior stakeholders. Reports to the VP, FP&A.

Qualifications

• 12+ years of experience in finance, FP&A, corporate strategy, investment banking, or related strategic finance roles.
• 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.

Responsibilities

• Lead components of the annual operating plan cycle with finance, strategy, and business leaders.
• Evaluate strategic investment opportunities and allocate resources to high-priority initiatives.
• Build financial models, business cases, and decision frameworks to support prioritization and ROI assessment.
• Develop reporting and insights on plan performance and investment progress for senior leadership.
• Synthesize complex inputs into concise recommendations for executives.

Skills

Financial modeling

Business case development

Stakeholder influence

Executive communication

Project management

Education

MBA or CFA

Job description

Oscar Health seeks a Senior Director, Strategic Finance and Enterprise Planning to lead the annual operating plan cycle and translate priorities into financial plans and executive-ready materials.

You will build business cases, evaluate trade-offs, and guide resource allocation toward top initiatives, leveraging FP&A experience and strong modeling to influence senior stakeholders. Reports to the VP, FP&A.