Director – Accounting

Hi, we're Oscar. We're hiring a Director of Accounting to join our Accounting 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, Accounting will be the accounting lead for Oscar's recently acquired businesses and related platform operations, guiding their integration into Oscar's accounting and financial operations environment. You will oversee close processes, accounting and FinOps integrations, subledger activity, AR/AP commission accounting, and variance analytics in partnership with the business and FP&A. You will also help lead accounting integration for future M&A activity, including systems, data, controls, and reporting design.

This role will report to the Deputy Controller.

Work Location: This position is based in our New York City 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 - $236,912 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and annual performance bonuses.

Responsibilities:

• Direct end-to-end accounting for recently acquired businesses and related platform operations, including monthly and quarterly close, reconciliations, journal entries, supporting schedules, accounting conclusions, and control documentation.
• Manage accounting and financial operations integrations for acquired businesses, including process design, systems and data mapping, subledger flows, cross-functional handoffs, and transition readiness.
• Lead accounting operations for insurance-adjacent acquired businesses, including AR/AP accounting, insurance AMS accounting structure, data design, subledger journals, and reporting outputs needed by the business and FP&A.
• Provide accounting leadership for SaaS and technology-enabled insurance platforms, including revenue, receivables, partner activity, and related platform accounting processes.
• Prepare and review flux and variance analytics for acquired businesses, platform operations, and related integration activity; communicate key drivers and risks to Finance leadership and business stakeholders.
• Support accounting for future M&A activity, including diligence input, close-readiness, policy and control alignment, systems and data integration, and post-close accounting operations.
• Develop scalable policies, close calendars, reconciliations, controls, and process documentation; partner with Finance Operations, FP&A, Product/Engineering, Legal, Tax, and external auditors as needed.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• 10+ years of relevant accounting experience.
• Bachelor's degree in Accounting, Finance, or related field
• 2+ years of experience leading accounting close processes, reconciliations, journal entries, or financial reporting for a business line, subsidiary, platform, or acquired business.
• 2+ years of experience with accounting systems, subledgers, AR/AP accounting, revenue or receivables accounting, financial operations integrations, or data/process design.
• 2+ years of experience preparing or reviewing flux and variance analysis.

Bonus points:

• Experience in a similar accounting leadership role at a health insurance, Insurtech, SaaS, or platform business.
• Experience with M&A accounting, purchase accounting support, acquired-company integration, or post-close finance operations integration.
• Experience designing or managing insurance AMS, ERP, billing, receivables, payables, or subledger accounting processes.
• 4+ years of experience with US-based insurance companies or insurance-adjacent businesses.
• Experience leading people and working collaboratively across accounting, finance, technology, and business teams.