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Director of Medicare Sales

| Greater NYC Area


  • Build scalable Medicare distribution model for multiple markets across country
  • The Director of Sales is responsible for achieving assigned sales/membership growth targets through Medicare Certified agents
  • Supervise, cultivate and train External Channel (Agents) who sell the portfolio of products offered to Medicare beneficiaries
  • Recruit, Manage, and Distribute Leads to a network of Captive Agents who can only sell MA products
  • Ability to develop internal call center to work with Medicare eligible beneficiaries


  • identify and develop relationships with individuals and organizations that influence the buying behavior of our target consumer (e.g.; Providers, Regulators, Faith Based Organizations, and Associations)
  • Organize involvement in formal and on-the-job training to ensure an accurate understanding of our products, compliance/policy requirements, sales processes, brand and value proposition messages and sales systems
  • Facilitate engagement of EDCs in executing these plans and ensure that EDCs appropriately build and advance our brand and value proposition and represent our product portfolio and service offerings
  • Compliance: Ensure external agents adhere to sales and marketing guidelines associated with Medicare regulations, partner expectations , and company policies & procedures
  • Organize activities, leads and territories to ensure effective and efficient coordination across the territory
  • Ensure Compliance: Ensure agents adhere to sales and marketing guidelines associated with Medicare regulations, and company policies and procedures
  • Monitor sales results, trends and hold representatives accountable for achieving targets
  • Provide a structured certification process, training processes and the available systems tools
  • Demonstrate excellent communications skills both verbal and written
  • Effectively communicate complex information via in person presentations, phone conversations and emails
  • Organize and coordinate specific trainings, expos and boot camps for agents to drive sales
  • Provide agent support at a local level to assist agents in finding marketing opportunities to build their book of business
  • Ensures proper completion of contracts, marketing agreements, and documentation of sales targets. May administer programs and monitoring to ensure compliance with external agent credentialing and training requirements.
  • Acts as internal liaison and customer service resource for external producers relative to enrollment and policy questions, systems issues, and coordination of materials fulfillment

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.

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