Director, People Strategy

Oscar, New York

A better kind of health insurance company

The People team is the linchpin of Oscar’s values and culture--we bring, we build, we maintain, we strengthen. You will be responsible for aligning business objectives with employees and management in designated business units and will accelerate the effectiveness of our super-talented team by owning and/or supporting the following areas: benefits administration, compensation, employee relations, policy design and implementation, compliance with federal and state requirements, People analytics and ad hoc special projects and initiatives. This Director will support some of our most critical businesses.



  • Partner with the leaders in our New York office on business and HR issues
  • Provide exemplary HR leadership and strategic guidance to the business, helping this business grow and scale
  • Develop, recommend and implement personnel policies and procedures in partnership with Chief People Officer, VP of People Strategy, Legal, Compliance and Finance
  • Administer components of Oscar’s compensation and benefit programs
  • Maintain in-depth knowledge of legal requirements as well as compliance with federal and state employment law regulations
  • Manage and resolve employee relation matters in collaboration with the VP of People, including problem solving team, manager and individual challenges
  • Support Oscar’s leadership by providing solution-oriented human resources advice and counsel as well as driving and implementing decisions
  • Oversee talent management initiatives locally, including performance management and compensation processes
  • Drive and contribute to People analytics with the goal of optimizing Oscar programs and culture
  • Serve as one of the main points of contact for HR-related questions
  • Provide support and assistance to other People functions, as needed


About you:

  • BA/BS degree
  • Minimum of seven to ten years of human resource experience
  • Strong familiarity with government compliance regulations
  • Working knowledge of best practices and protocols
  • Strong attention to detail and the ability to deliver results in a timely manner
  • Ability to manage competing deadlines and work well under pressure
  • Exceptional interpersonal, problem-solving and organizational skills
  • Familiarity and interest in analytics and metrics
  • Experience at a rapidly scaling organization
  • A “no job too big or small” ownership attitude


Nice to Haves:

  • HR certifications (i.e. SPHR, PHR, SHRM-SCP)
  • Supported tech companies

At Oscar, being an Equal Opportunity Employer means more than upholding discrimination-free hiring practices. It means that we work to cultivate an environment where exceptional people can be their most authentic selves and find both belonging and support. We're on a mission to change healthcare -- an experience made whole by your unique background and perspectives.

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. 

Pay Transparency Policy: Oscar's Pay Transparency Policy ensures that you won't be discharged or discriminated against based on whether you've inquired about, discussed, or disclosed your pay. Read the full policy here.

About Oscar

Founded in 2012, Oscar is probably the last thing you would expect from a technology startup – a seemingly old-fashioned healthcare insurance provider. The company provides clients with the kind of clarity and simplicity we have come to expect from an e-commerce site. And, of course, they're hiring.

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