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Helping you save time and money, by providing high quality, affordable health plans

Manager, Benefits

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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 (accommodations@hioscar.com) 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.

Health insurance

Of course. Oscar employees get great health insurance for themselves and their families.


We want you to be able to save for a long retirement.

Unlimited pto

There's no limit to the number of vacation days you can take as a salaried employee. We work hard and encourage employees to recharge.

Fully stocked kitchens

Great coffee, healthy snacks, and catered lunches make it easy to stay energized at work.

Company social events

Monthly happy hours, outings, and an annual retreat create fun opportunities to connect with coworkers.

Volunteer with us

Join us for a variety of volunteer opportunities throughout the year.

Oscar Health at a glance

Helping you save time and money, by providing high quality, affordable health plans

Oscar Health focuses on Healthcare, Information Technology, Insurance, Technology, and Health and Insurance. Their company has offices in Los Angeles, New York City, New York, Dallas, and Tempe. They have a very large team that's between 1001-5000 employees. To date, Oscar Health has raised $1.268B of funding; their latest round was closed on August 2018 at a valuation of $3.6B.

You can view their website at http://hioscar.com or find them on Twitter, Facebook, and LinkedIn.