Head of People Operations at Oscar

We are Oscar

Headquartered in New York City, Oscar is aiming to revolutionize health insurance. The Oscar team is focused on utilizing technology, design and data to humanize healthcare.

We are changing how health insurance works. We want to create a healthcare experience that’s intuitive and puts people, not cost or workflows, first. We’re using a consumer-focused and tech-driven approach to do so. This positions us uniquely in the space - and creates one of the biggest opportunities in healthcare.

We brought together leaders from top technology, service and healthcare companies to deliver on our promise and seize this opportunity. We all work side by side in a collaborative, energetic, and creative environment. The result: better people, better ideas, and better healthcare.

The role:

The Head of People Operations will direct the design and operations of the organization's employee focused technology platforms (including Oscar’s HCM Platform), as well as direct and administer the implementation of a new HCM Platform. You will manage prioritization of the HCM projects and build and delivery of HR analytics, metrics, and custom tools.


  • Create and implement a common methodology and tools for project management, data management and testing
  • Be a primary leader for the coordination of testing and migration approval for HR technology changes
  • Serve as the point of contact to Technology for HR platforms and systems and partner with them to ensure successful integration with other corporate systems.
  • Identify and execute opportunities for improving the effectiveness of processes, systems, and reports. Drive system enhancements using project management methodology. Continually review processes to identify and optimize systems solutions and the potential for automation.
  • Build and deliver HR analytics, metrics, and scorecard utilizing reporting tools. Consult with and present to senior management teams as required.
  • Ensure HR system data security, integrity, and accuracy. Oversee maintenance of data and assure that data is available in a timely manner.
  • Provide guidance on complex or escalated HR system issues. Act as resource to troubleshoot all HR system related discrepancies and provide problem resolution.
  • Manage HCM Platform system steady state including monitoring of system and employee issues. Suggest system and process improvements.
  • Lead the development, delivery, and maintenance of Oscar’s new HCM Platform system end-user training and education as well as other relevant platforms

Who are you?

This person should be passionate about data and technology with a background in HR. In addition, this person should have:

Qualifications and expertise include:

  • Bachelor’s degree in human resources, information systems, or related field, or equivalent experience
  • 8+ years experience and prior experience in the implementation, development, and functional support of an enterprise level HR system.
  • Experience in managing medium size projects
  • Experience with Workday a plus
  • Knowledge of integrated systems reporting

Above all else:

  • Friendly, thoughtful, and kind.
  • Humility, maturity, and lack of ego.
  • Always a point of view and an open mind.



Oscar is an equal opportunity employer. Should you be a fit for this role, one of our recruiters will contact you from a hioscar.com e-mail address. Oscar recruiters do not request your sensitive personal information by email. 

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