Senior Manager, Benefits

Oscar, Arizona

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 Sr. Manager of Benefits for our Total Rewards team. In this role, you will be responsible for managing 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 collaborating with internal stakeholders … operations for Oscar. The role will report to our Head of Total Rewards.

Here at Oscar 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. 

During your first six weeks, you should have:

  • Developed an in depth understanding of our current benefit plans and offerings
  • Developed an in-depth understanding of our People team workflow and processes
  • Begun to independently respond to escalated benefits issues requiring analysis
  • Developed working relationships with key internal and external stakeholders
  • Begin to become a critical source of support for our employees for benefits
  • Developed working relationships with benefit vendors and carriers
  • Developed a collaborative partnership with People Operations and Finance to create streamlined internal operations.
  • Begin to familiarize yourself with Workday Benefits

Afterwards and on an ongoing basis, you will:

  • Benefits Design: Analyze current benefits and evaluate future potential benefits to ensure we're investing in the right areas to hire and retain diverse top talent (including NY Tech talent market and AZ operational talent market).
  • Partner with business leaders to understand efficacy of benefits package through time, as a talent retention tool and as an offering that supports our business goals
  • Prepare and manage Oscar’s internal Open Enrollment in partnership with Total Rewards leader.
  • Develop communication tools to enhance company-wide understanding of our benefits package in partnership with our Director of Internal Communications.
  • Employee Enablement & Support: Coordinate daily benefit processing by providing exemplary support to employees on benefits inquiries and escalated issues in partnership with benefit broker and vendors.
  • Partner with HRIS team to ensure Workday system data integrity by addressing system queries/issues, testing system changes, and analyzing data.
  • Generate monthly and on-demand report requests, custom reports for internal requests; assist in the development of complex reports.

About you:

  • 7+ years of benefit experience with a proven track record of success
  • Bachelor’s degree required
  • Experience with creating benefits offerings for similar companies (Tech and/or fast-growth start-ups)
  • Knowledge of the 5500 filings, 1094/95C, and NDT relative to 401K
  • You are an overachiever - you never quit, never back down from a challenge, and never satisfied with the status quo
  • You have excellent verbal and written communications with the ability to break down complicated topics into simple terms
  • You are excited by the challenges of working at a constantly evolving, high-growth start-up that will require you to build the tools and processes you need to do your job well
  • You are highly organized, diligent about prioritizing projects, and capable of managing a complex process
  • You have a strong sense of urgency, a bias for action, and thrive in fast paced environments
  • You are an eager collaborator that likes to problem solve and tackle issues systematically and head on
  • You are passionately committed to going above and beyond to deliver a great experience to employee
  • You are comfortable working in an ever-evolving environment where no two days look the same

Nice to Haves:

  • HR certifications (i.e. SPHR, PHR, SHRM-SCP)
  • Experience with Workday and Workday Benefits
  • Experience creating wellness-based programming


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.

Be a Better Oscar Candidate

Learn skills and get an insider's look at Oscar when you watch classes taught by their top employees.

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