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Associate Director, Technology Finance Operations

Oscar Health

Oscar Health

IT, Accounting & Finance, Operations
New York, NY, USA
Posted on Tuesday, October 24, 2023

Hi, we're Oscar. We're hiring an Associate Director, Technology Finance Operations to join our Technical Operations team.

Oscar is the first health insurance company built around a full stack technology platform and a 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 Associate Director, Technology Finance Operations works with aligned leadership to scale and run the organization as we drive to meet our strategic goals. The role also works with leaders across the company, including Financial Planning & Analysis (FP&A) colleagues, IT and external vendor contacts to solve complex problems, drive solutions, and orchestrate operational initiatives.

As the Associate Director, Technology Finance Operations, you will be responsible for establishing processes to track the aligned organization’s financial position and vendor relationships, including direct management of offshore/nearshore contracting partners. In addition, you will be responsible for supporting strategic planning processes through establishing and managing administrative expense budgets for the organization.

Demonstrating strong business acumen and strategic thinking abilities, you will act as a thought partner for the aligned businesses and drive them to act as cohesive budget owners that make business decisions in a unified way. Monitor the organization's day to day financial position and provide executive-level updates.

You will report to the Senior Director, Tech Operations.

Work Location:

Oscar is a blended work culture where everyone, regardless of work type or location, feels connected to their teammates, our culture and our mission. This is a hybrid role in our New York City office. You will work part of the time in the office and part of the time remote / work-from-home. #LI-Hybrid

Pay Transparency:

The base pay for this role in the states of California, Connecticut, New Jersey, New York, and Washington is: $144,000 - $189,000 per year. The base pay for this role in all other locations is: $129,600 - $162,000 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, and annual performance bonuses.


  • Responsible for creating and delivering reports that support budget management, including monthly budget vs. actual analysis, headcount reports, expense forecast updates, ensuring their quality, timeliness, and accuracy.
  • Communicate regularly with technology leaders to understand variances and facilitate conversations to manage these variances. Provide executive level summaries of overall budget position.
  • Work with FP&A to identify expense trends and analyze key drivers of costs; participate in the strategic planning processes including measuring progress towards short-term and long-term administrative expense targets.
  • Directly manage vendor relationships for our offshore/nearshore contracting partners. Perform as a bridge between contracting vendors and internal stakeholders. Troubleshoot any problems and present to management as required. Collaborate with IT and hiring managers to ensure contractors are onboarded efficiently and effectively.
  • Work with procurement and other leaders to indirectly manage software vendors, ensuring new vendors follow our enterprise-wide processes and established vendors are monitored and renewed as needed.
  • Establish processes and metrics to track, measure, report and evaluate vendor performance.
  • Implement process improvements to complete work efficiently and effectively.
  • Compliance with all applicable laws and regulations.
  • Other duties as assigned.


  • 7+ years of professional experience, BA/BS Degree or equivalent experience required
  • 6+ years of work experience in finance and/or accounting
  • 5+ years of vendor management experience (negotiating contracts, managing renewals, tracking spend)

Bonus Points

  • Experience working with outsourcing vendors
  • Experience negotiating with with SaaS vendors
  • Headcount / Position management experience
  • Experience using Workday Adaptive Planning and/or other Workday modules
  • Business financial acumen; familiarity with budgets and financial reports.

  • Highly skilled in spreadsheet tools, including Excel/Google Sheets.
  • Comfortable synthesize information for an executive audience
  • Executive presence and ability to communicate with, influence, and manage stakeholders, including VP-level executives

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.

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 ( to make the need for an accommodation known.