Senior Director, Strategic Finance & Enterprise Planning

Oscar Health•Dallas, TX

4d•$196,733 - $258,212•Remote

About The Position

Oscar is hiring a Senior Director of Strategic Finance & Enterprise Planning to join its Strategic Finance team. The role helps 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. It also drives the strategic investment process through business cases, evaluation of trade-offs, and support for resource allocation toward high-priority initiatives. The position calls for FP&A or strategic finance experience, strong financial modeling, and judgment to influence senior stakeholders. This is a fully remote position open to candidates who reside in Dallas, Texas. Oscar notes that its approach to work may adapt over time, potentially involving a hybrid presence at the hub office associated with the candidate’s metro area. The role reports to the VP, FP&A. Base pay is $196,733–$258,212 per year, with eligibility for employee benefits, unlimited vacation, company equity grants, and annual performance bonuses.

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.
Ability to influence senior stakeholders and drive alignment across cross-functional teams.
Excellent communication skills and 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.

Nice To Haves

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

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 to 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 reporting and insights on plan performance, investment progress, risks, and opportunities for senior leadership.
Synthesize complex financial and operational inputs into concise recommendations for executive discussions.
Identify opportunities to improve planning accuracy, resource allocation, and investment discipline across the organization.
Comply with all applicable laws and regulations.
Perform other duties as assigned.