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Oscar Health // health insurance
Los Angeles, California, United States    Posted: Thursday, September 03, 2020
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Hi, we're Oscar. Were hiring a Cigna + Oscar Sales leader to join our Growth team in our California office. 

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:

The Cigna + Oscar Sales leader will be responsible for growth & distribution for the entire Cigna + Oscar product line in your region. You will be heavily focused on growth & will be responsible for making investment decisions to incentivize distribution partners & managing distribution budgets. You will also be a stakeholder on expansion planning, plan design, & pricing within the respective region. Youll be responsible for developing & managing key distribution relationships & driving strategic decisions for the line of business. 

Your areas of focus will be:

  • Oscars Cigna + Oscar product & sales: building & maintaining key relationships/partnerships, maximizing production & ensuring productivity, organization & effectiveness across the Regional C+O Sales Teams 
  • Reaching small group targets & facilitating strategic distribution partnerships for this line of business 

You will report to Oscars Senior Vice President of Growth, Louis DeStefano. 


  • Meet or exceed regional sales goals while opening doors to additional distribution channels & providing excellent service to existing distribution partners
    • Identify distribution partners, develop relationships with key partners, & manage ongoing production & expectations with agencies
    • Track & manage distribution partner KPIs
    • Manage CAC/LTV & the impact of distribution decisions on contribution margin
  • Represent market dynamics & traction with Small Group leadership team
    • Partner with Small Group leadership to identify distribution opportunities, including bonus programs, commissions, eligibility rules, etc.
  • Ensure regional Cigna + Oscar sales teams are operationally effective
    • Build, develop & manage best in class regional sales organization
    • Build performance management framework to measure team KPIs 


  • 10+ years of experience in employer-based health insurance sales
  • Experience building, developing & managing health insurance sales teams
  • Experience leading cross-functional initiatives

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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