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Oscar Health // health insurance
Sales, Full Time    Dallas, Texas, United States    Posted: Wednesday, September 30, 2020
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Hi, we're Oscar. Were hiring a Sales Director to join our Sales team, in the Central Region. 

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

About the role:

As a key member of Oscars sales team, you will lead the companys sales efforts in the Central Region. Youll be responsible for growing membership in Oscars individual & family (IFP) & Medicare Advantage (MA) health insurance products through the implementation of traditional insurance sales channels as well as the pursuit of innovative sales strategies. You will drive Oscars broker strategy in the state, ensuring that insurance brokers across our coverage area have the information & tools to effectively sell Oscar. On the creative side, youll test & iterate on ideas to drive buzz at a local level & create efficient pathways for individuals to enroll with Oscar. Examples could include building relationships with influential organizations & individuals in the local market, or conceiving & planning large-scale enrollment events. This is a unique opportunity to have a significant impact on the trajectory of a rapidly growing startup in a region holding more than 25% of our membership base.

You will report to Oscars SVP of Growth, Louis DeStefano. 


  • Meet or exceed regional sales goals while opening doors to additional distribution channels & providing excellent service to existing distribution partners
    • Drive our Central Regions broker/distribution partner strategy to bolster their ability to sell Oscar
    • Identify distribution partners, develop relationships with key partners, & manage ongoing production & expectations with agencies
    • Track & manage distribution partner KPIs & develop innovative ways to incent increased sales productivity & brand loyalty
    • Manage CAC/LTV & the impact of distribution decisions on contribution margin
  • Represent market dynamics & traction with IFP & MA leadership team
    • Partner with IFP & Medicare Advantage leadership to identify distribution opportunities, including bonus programs, commissions, eligibility rules, etc.
    • Provide local competitive intelligence & market research for internal Oscar teams
    • Support Oscar HQ Business team & Regional Market Leader efforts to evaluate geographic expansion, new product lines, insurance plans & pricing
  • Ensure regional IFP & Medicare Advantage sales teams are operationally effective
    • Build, develop & manage best in class regional sales organization
    • Build performance management framework to measure team KPIs 


  • 7+ years of experience in health insurance sales
  • Experience building, developing & managing health insurance sales teams
  • Cross-functional leadership experience 
  • Experience driving revenue growth 
  • Experience developing innovative ways to reach prospective members

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 & find both belonging & support. We're on a mission to change health care -- an experience made whole by our unique backgrounds & perspectives.

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

Reasonable Accommodation:

Oscar applicants are considered solely based on their qualifications, without regard to applicants 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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