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Financial Transformation Director

Oscar

New York, New York, United States (New York, NY) Hybrid permanent

Posted: March 19, 2026

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Quick Summary

We're looking for a highly skilled Financial Systems Director to join our team and lead financial system development, process analysis, and project management. The ideal candidate will have experience in financial systems and a strong background in healthcare, IT, and finance.

Job Description

Hi, we're Oscar. We're hiring a Director, Financial Systems 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, Financial Systems leads a team focused on maintaining and developing Oscar’s financial systems, analyzing existing processes, creating new processes and systems for scale, and managing various projects simultaneously to support Oscar’s fast growing business.

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:

• Lead a high-performing team of finance professionals, providing guidance, mentorship, and development opportunities.

• Continually evolve and manage a strategic roadmap for finance transformation aligned with the organization's overall objectives and goals.

• Collaborate with cross-functional teams, including IT, operations, and business units, to drive alignment and integration of finance transformation efforts with broader organizational objectives.

• Lead change management efforts to ensure smooth adoption of new processes, systems, and ways of working within the finance team and across the organization.

• Identify inefficiencies in existing financial processes and workflows and lead efforts to streamline and optimize them.

• Evaluate, select, and implement new financial technologies and systems to improve efficiency, accuracy, and decision-making within the finance function.

• Manage critical business strategies by maintaining and further developing the finance ecosystem (technology and process) collaborating cross-functionally with FP&A, Accounting, People, and other system stakeholders.

• Lead deployment of home grown and cloud-based tools released for our financial system; including requirements, testing and communication to key stakeholders.

• Develop, document, and implement policies, procedures, guidelines, and best practices to ensure data integrity, standardized end-user processes and minimize manual intervention.

• Design business solutions to allow for integration between finance systems; foster a culture of continuous improvements.

• Compliance with all applicable laws and regulations.

• Other duties as assigned.

Requirements:

• Bachelor’s degree in Accounting, Finance, or related field; or 4 years of relevant experience.

• 10+ years experience in finance, accounting, or related roles, with a track record of leading successful finance transformation initiatives.

Bonus points:

• Experience in a similar position at a health insurance company.

• Experience leading people and working collaboratively across the organization.

• Experience managing large scale system implementations.

• Workday Financial training certifications.

• Workday Financials implementation experience.

• NetSuite experience.

• Google BigQuery experience.

• Adaptive Planning implementation experience.

This is an authentic Oscar Health job opportunity. Learn more about how you can safeguard yourself from recruitment fraud here.

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.

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