Financial Transformation Director

Hi, we're Oscar. We're hiring a Financial Transformation Director to join our 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 Director, Finance Transformation is a senior leadership role responsible for defining and spearheading the long-term strategic roadmap for finance processes, systems, and performance across the organization. This role will be accountable for the overall vision, governance, and successful integration of transformation efforts into the company's broader financial health. This role involves high-level strategic planning, senior stakeholder influence, and building a high-performing team to deliver scalable financial infrastructure.

You will report into the VP, Financial Systems.

Work Location: This position is based in our New York office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency: The base pay for this role is: $180,504 - $236,911 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and annual performance bonuses.

Responsibilities:

• Define and own the multi-year Finance Transformation roadmap, ensuring it scales with organizational growth and aligns with enterprise-level financial objectives.
• Act as a key advisor to the CFO and senior leadership, driving alignment across IT, Operations, and Business Units to ensure transformation efforts support overall company strategy.
• Lead the design and implementation of global Target Operating Models (TOM) to optimize large-scale operations and drive long-term performance improvements.
• Oversee comprehensive, organization-wide change management strategies, ensuring the Finance function and broader business units adapt successfully to new systems and processes.
• Accountable for the successful delivery of a portfolio of transformation projects, including budget approval, resource allocation, and ROI tracking.
• Establish and enforce standards for financial process optimization and efficiency, ensuring all improvements meet regulatory and internal policy requirements.
• Maintain ultimate accountability for compliance with all applicable laws, regulations, and internal audit requirements within the transformation scope.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• 10+ years of professional experience in finance, accounting, or business strategy
• Bachelor's degree in finance, accounting, or business administration
• 8+ years of experience in project and portfolio management, specifically leading large-scale finance transformation programs.
• 5+ years of experience leading complex financial systems implementations (e.g., Workday Financials) and applying advanced change management principles.

Bonus points:

• Master's degree in finance, accounting or business strategy; or MBA strongly preferred
• Extensive experience leading and developing high-performing teams and working collaboratively across an executive suite.
• Proven track record in a senior position within a health insurance or highly regulated environment.
• Workday Financial training certifications and experience with global, multi-entity implementations