Strategic Finance & Enterprise Planning Leader

Oscar Health; Phoenix (AZ); Hybrid; USD 197,000 - 258,000; Full time

Job summary

Oscar Health is seeking a Senior Director of Strategic Finance and Enterprise Planning to lead the annual operating plan cycle, partnering with Finance, Strategy, and business leaders to translate priorities into financial plans and executive-ready materials.

You will report to the VP, FP&A and drive the strategic investment process by building business cases, evaluating trade-offs, and guiding capital allocation for top initiatives.

Qualifications

• 12+ years of experience in finance, FP&A, corporate strategy or 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, with the ability to translate analysis into executive-level recommendations.
• Strong project management skills and comfort operating in complex, fast-paced environments.
• High degree of ownership, balancing strategic thinking with operational execution.

Responsibilities

• Lead components of the annual operating plan cycle with Finance, Strategy, and business leaders to translate priorities into financial plans, targets, and investment decisions.
• Partner with business leaders to evaluate strategic investment opportunities, assess trade-offs, and ensure resources are allocated to top priorities.
• Build financial models, business cases, and decision frameworks to support investment prioritization and ROI assessment.
• Develop clear reporting and insights on plan performance, investment progress, risks and opportunities for senior leadership.
• Support executive discussions by synthesizing complex 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.

Skills

Financial modeling

Analytical skills

Business case development

Stakeholder influence

Communication skills

Project management

Ownership mindset

Job description

Oscar Health is seeking a Senior Director of Strategic Finance and Enterprise Planning to lead the annual operating plan cycle, partnering with Finance, Strategy, and business leaders to translate priorities into financial plans and executive-ready materials.

You will report to the VP, FP&A and drive the strategic investment process by building business cases, evaluating trade-offs, and guiding capital allocation for top initiatives.