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.
This is an authentic Oscar Health job opportunity.
At Oscar, being an Equal Opportunity Employer means more than upholding discrimination-free hiring practices. It means that we cultivate an environment where people can be their most authentic selves and find both belonging and support. We're on a mission to change health care -- an experience made whole by our unique backgrounds and perspectives.
Pay Transparency: Final offer amounts, within the base pay set forth above, are determined by factors including your relevant skills, education, and experience. Full-time employees are eligible for benefits including: medical, dental, and vision benefits, 11 paid holidays, paid sick time, paid parental leave, 401(k) plan participation, life and disability insurance, and paid wellness time and reimbursements.
Artificial Intelligence (AI): Our AI Guidelines outline the acceptable use of artificial intelligence for candidates and detail how we use AI to support our recruiting efforts.
Reasonable Accommodation: Oscar applicants are considered solely based on their qualifications, without regard to applicant’s disability or need for accommodation. Any Oscar applicant who requires reasonable accommodations during the application process should contact the Oscar Benefits Team ([email protected]) to make the need for an accommodation known.
California Residents: For information about our collection, use, and disclosure of applicants’ personal information as well as applicants’ rights over their personal information, please see our Privacy Policy.
Skills Required
- 10+ years of relevant accounting experience
- Bachelor's degree in Accounting, Finance, or a related field
- 2+ years 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 preparing or reviewing flux and variance analysis
- 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 collaborating across accounting, finance, technology, and business teams
Oscar Health Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Oscar Health and has not been reviewed or approved by Oscar Health.
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Healthcare Strength — Employer-sponsored medical coverage for employees and their families with mental-health support is prominently offered. Wellness programming and digital care access add to perceived strength.
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Parental & Family Support — Paid parental leave of 10+ weeks, backup care, and family-forming support (including fertility and adoption benefits) are part of the package. Reproductive‑loss leave is also noted.
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Leave & Time Off Breadth — Multiple time‑off options, wellness days, and an unlimited vacation program for some roles are described. Paid holidays, paid sick time, and a long‑tenure sabbatical broaden time‑away choices.
Oscar Health Insights
What We Do
Oscar Health, Inc. (NYSE: OSCR) is a leading consumer health company that gives people power over their healthcare. Oscar Health serves millions of consumers, employers, brokers, and partners through Oscar Insurance, Lucie Health Marketplace, and Trove Group. Together these businesses deliver exceptional lifestyle products and technology platforms that make healthcare easy to choose, use, and experience.
