Head of Compensation

Oscar, New York

A better kind of health insurance company

Hi, we’re Oscar.

We are changing how health insurance works. Our goal is to make health insurance simple, transparent and human. We need your help to do so. We brought together leaders from top technology, service and healthcare companies to work side by side to disrupt health insurance. The result? Better people, better ideas, and better healthcare.


About the Role:

The People team is the linchpin of Oscar’s values and culture--we bring, we build, we maintain, we strengthen. We are hiring a Head of Compensation to strengthen and lead our compensation and equity programs. This person will be responsible for maintaining internal consistency and external competitiveness through the design, development, and implementation of a strategic compensation philosophy and plan. The Head of Compensation will work with leaders across the organization to ensure alignment with Oscar’s goals and business objectives.

Here at Oscar we move quickly, are continuously iterating on our processes, and driving change through innovation. We’re looking for an analytical thinker who can not only develop a strategic vision for our compensation program, but effectively operationalize and drive engagement along the way.



During your first six weeks, you should have:

  • Developed an in-depth understanding of our People team workflows and processes.
  • Developed an in-depth understanding of our current compensation philosophy and practices.
  • Built effective working relationships with key stakeholders, both internal and external .
  • Become familiar with Workday compensation modules.
  • Become familiar with Shareworks, our equity management system.


Afterwards and on an ongoing basis, you will:


  • Manage the administration of direct compensation (executive, exempt & non exempt and cash compensation programs-- both merit and incentive-based).
  • Manage the merit and bonus/incentive processes and make program design recommendations based on relevant market data as defined by company compensation philosophy.
  • Ensure internal equity through the analysis of existing compensation policies, guidelines and procedures.
  • Manage equity planning, administration, monitoring and reporting in partnership with Legal and Finance.
  • Participate in market-relevant surveys and frequently benchmark best practices in order to maintain competitive positioning and recommend new plans and revisions that are cost effective and consistent with compensation trends and corporate objectives.
  • Guide People Team Leadership through pay decisions, policy and guideline interpretation, job evaluation, and pay equity; including the development of creative, compensation-related programs.
  • Partner with People Team Leadership and Finance Leadership on headcount planning and budget forecasting.
  • Recommend and implement enhancements to Compensation modules in Workday and integration with Shareworks, while maintaining data integrity across all compensation-related platforms.
  • Partner with our internal communications team to drive employee engagement and understanding regarding employee performance, incentives and compensation
  • Ensure that all aspects of plan design and administration remain in compliance with applicable laws.


Winning factors: What leads to success

  • Bachelor’s Degree
  • 7+ years of relevant experience in compensation analysis and equity administration
  • 5+ years of management experience
  • Expertise in policy design and understanding of relevant regulations
  • Deep expertise in equity administration, including accounting, tax and legal implications
  • Strong business acumen with the ability to learn and understand financials, and relay learnings to the business
  • Familiarity with Workday and Shareworks, preferred
  • Exceptional analytical, prioritization, and problem-solving skills
  • Ability to thrive in an ambiguous, fast-paced environment
  • Ability to work autonomously, but take direction as needed
  • Strong project management skills: good follow-through on cross-functional plans, projects and goals
  • Excellent written and verbal communication skills and presentation skills; with the ability to tailor communication to a variety of stakeholders
  • Results- oriented and able to balance multiple priorities, working quickly and nimbly
  • Strong collaborator and influencer; able to build strong partnerships with internal and external partners
  • You are a self-starter who loves taking initiative and proactively provide suggestions to streamline and improve processes



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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