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Associate Director, Operations Transformation & Strategy

oscar · 9 days ago
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Hi, we're Oscar. We're hiring an Associate Director to join our Operations Transformation & Strategy 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

We are looking for a high-performing Associate Director to join our Ops Transformation & Strategy team. This is a fast moving team focused on creating value in Operations: increasing efficiency, reducing costs, reducing risk, building for scale, increasing member and provider experience, driving innovation, and more. The team reports to the company COO and focuses on top priority areas of the business. On a project basis, you will collaborate with the leaders in various departments to diagnose critical issues and root causes, assess processes and capabilities end to end, propose and execute on a path towards a more optimal state.

You will report to the Senior Director, Operations Transformation & Strategy.

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 is: $158,400 - $207,900 per year. You are also eligible for employee benefits, participation in Oscar’s unlimited vacation program and annual performance bonuses.


  • Leads the end-to-end management of cross-functional implementations/projects, including project plan creation and stakeholder engagement. The goal is to drive collaboration, mitigate edge cases, ensure on-time completion, and maximize impact.
  • Collaboratively works with all relevant internal and external stakeholder to formulate implementation, communications, and program strategies for successful change management and risk mitigation
  • On a project basis, performs current state assessment of processes and performance followed by collaboration with subject matter experts to identify solutions
    • Lead the creation, gathering, analyzing and interpreting of data and metrics to enable our strategic goals and measure impact
  • Drive and execute on the department strategy to enhance program’s overall value including determining and uncovering new opportunities 
  • Compliance with all applicable laws and regulations
  • Other duties as assigned


  • 7+ years experience in healthcare strategy and operations, and or related field
  • 4+ years of experience managing individual contributors 
  • 3+ years project planning experience

Bonus points

  • MBA, MPH, MD 
  • Management Consulting experience with a focus on healthcare 
  • Experience using data analytics to improve programs
  • Experience using Excel/Sheets (charts, pivot tables, advanced formulas) and PowerPoint/Slides
  • Experience in a fast-paced operations or strategy environments, and operating with many stakeholders
  • Experience mentoring more junior colleagues
  • Experience executing enterprise-wide projects: defined project plans, coordinated resources, managed implementation activities, and developed all processes associated with program rollout and ongoing support
  • Healthcare experience (Health Insurance, Health Systems, or Healthcare Consulting)

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.

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 Notice to Job Applicants.

Last updated on Jul 9, 2024

See more

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