Manager, Benefits

Oscar, Tempe, Arizona, United States

A better kind of health insurance company

Hi, we're Oscar. We’re hiring a Benefits Manager to join our Total Rewards team in our Arizona office. 

Oscar is a technology-driven, consumer-focused health insurance startup founded in 2012 and headquartered in New York City. Our goal is to make health insurance simple, transparent, and human. We need your help to do so.

About the Role:

The People Team is the linchpin of Oscar’s values and culture--we bring, we build, we maintain, we strengthen. We move quickly and are perpetually introducing new ideas. We need you not only to be able to think analytically and strategically, but, just as important, to execute on those ideas. 

We are hiring a Benefits Manager to manage the day-to-day operations of Oscar’s benefits programs (health, dental, vision, short-term and long-term disability, life insurance, flexible spending plans, 401(k) plan, and voluntary benefits), vendor relationships, and advise internal stakeholders. You will report into the Director of Total Rewards.


  • Develop an in depth understanding of our current benefit plans and offerings, and the Workday Benefits module
  • Develop an in-depth understanding of our People team workflow and processes
  • Respond to escalated benefits issues 
  • Build working relationships with key internal and external stakeholders, including benefits vendors and carriers
  • Partner with People Operations and Finance to create streamlined internal operations
  • Prepare and manage Oscar’s internal Open Enrollment in partnership with your Total Rewards team
  • Develop communication tools to enhance company-wide understanding of our benefits package in partnership with our communications team
  • Partner with People Operations team to ensure Workday system data integrity by addressing system queries/issues, testing system changes, and analyzing data
  • Generate and analyze monthly and on-demand reporting requests


  • Bachelor’s degree
  • 5+ years of benefits experience 
  • Experience creating benefits offerings for tech and/or fast-growth start-ups
  • Experience managing 5500 filings, 1094/95C, and NDT relative to 401K

Bonus points:

  • HR certifications (i.e. SPHR, PHR, SHRM-SCP)
  • Experience with Workday and Workday Benefits
  • Experience creating wellness-based programming
  • Experience presenting complex information across varying levels of seniority
  • Project management experience


Life at Oscar: 

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.

We aim to make health care affordable and accessible for all, and apply this same vision to our perks and benefits, including: medical benefits, unlimited paid-time off, paid parental leave, retirement plans, company social events, stocked kitchens, wellness programs, and volunteer opportunities.

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 ([email protected]) to make the need for an accommodation known.

Pay Transparency Policy:

Oscar 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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Want to learn more about Oscar? Visit Oscar's website.