Medicare Advantage Sales Agent

Meet The Team

Job Description

Job Description

Hi, we're Oscar. We’re hiring a Medicare Advantage Sales Agent to join our team in New York.

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: 

Oscar Regional Sales is a small, nimble team focused on driving growth in each of our markets. We want strong and passionate Medicare Advantage Sales Agents with established provider and community relationships to help launch and grow Oscar in assigned territories. 

Representing Oscar to the market, you will be responsible for driving membership growth through  traditional insurance sales channels, as well as the pursuit of innovative sales strategies. On the traditional side, you will be out in the field building relationships with providers and community organizations, and making presentations to potential qualified Medicare participants where they are -- virtually, in-home, doctor’s offices, and/or community / sales events -- using approved governmental guidelines. On the creative side, you’ll test and iterate on ideas to drive buzz at a local level and nurture partnerships with local organizations to enroll individuals in these plans. 

If you enjoy impacting others’ lives and want a role where you can have an immediate impact on the trajectory of a rapidly growing healthcare startup in a massive and important market, then this role is for you.


  • Develop strong and lasting relationships with prospects, providers and community partners to secure self-generated leads
  • Become the “owner” of your assigned territory to maximize sales and marketing efforts in attaining new enrollments
  • Prospect for leads and convert leads into appointments, into enrollments 
  • Meet or exceed sales goals while providing great service 
  • Be the voice of consumers within Oscar
  • Maintain enrollment rate that is deemed acceptable by the company and conduct member retention activities as assigned
  • Coordinate and conduct approved marketing and sales events with providers and community partners
  • Ensure market adherence to Medicare guidelines and compliance regulations
  • Achieve corporate enrollment goals
  • Work cross functionally as needed to deliver upon the Oscar mission and goals


  • 2+ years of sales experience in a managed health care setting
  • Active New York Health & Life Insurance Licenses with valid state driver’s license
  • High School Diploma
  • Bilingual (English and Spanish)
  • Experience communicating with and presenting to a wide range of audiences from potential members and community organizations to internal leadership
  • Upon offer acceptance you must be able to complete and pass the AHIP certification (paid for by Oscar Health)

Bonus points: 

  • Bachelor’s degree
  • Experience working in a fast-paced environment

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 (************** 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.

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