Demo

Medicare Outside Sales Representative

Healthfirst
York, NY Full Time
POSTED ON 4/22/2026
AVAILABLE BEFORE 5/22/2026
The Medicare Outside Sales Representative is a top performing membership growth agent responsible for identifying, educating, and enrolling prospective Medicare Advantage (MA) beneficiaries in the appropriate MA plan based on prospect’s needs and qualifications. The Outside Sales Rep explains program benefits in a manner that is compliant with the Center for Medicaid and Medicare Services (CMS) and company policies and regulations. This role will come with challenging goals and targets as part of a competitive sales incentive plan designed to reward top performers. This individual must be goal oriented and an expert at grassroots marketing to create new sales locations and penetrate geographies and markets where HF holds lower market penetration. The Outside Sales Rep must be able to generate their owns leads through myriad marketing activities. They must possess a deep understanding of and extensive experience in organizing sales activities to engage prospective members in distinct communities. The Outside Sales Rep will collaborate closely with the Delivery Services Engagement (DSE) team that works with in-network clinical providers to promote Healthfirst and ensure visibility, ultimately increasing market share. The Outside Sales Rep will also be responsible for driving retention efforts, so that Healthfirst members maintain consistent health insurance coverage to avoid gaps or disruptions in care.

Duties & Responsibilities


  • Drive membership growth by acquiring new members while also meeting aggressive retention targets.
  • Work directly with community-based organizations, providers, sales locations, and other sources to develop self-generated referral channels resulting in increased enrollments.
  • Identify potential members and design plans to educate them on the available benefits plans and features that are tailored to the member’s needs and eligibility.
  • Live Healthfirst’s mission of “Members are our North Star” to ensure that our goal and activities are guided by member needs and preferences.
  • Ensure a superior customer experience through consistent and timely service, follow-up, and plan benefit reviews.
  • Ensure the right member is in the right plan.
  • Deliver effective sales presentation to consumer groups, individual prospects and community or provider partners.
  • Determine and recommend (and/or partner on) to Community Engagement to organize events within the territory including but not limited to health fairs, holiday-themed events,provider sponsored events as well as health-related theme events.
  • Partner with DSE for scheduling face to face meetings with Hospitals, IPA’s, and community providers to engage, education and identify related issues. Inform DSE of related issues andappropriately follow up with updates when needed.
  • Strictly adhere to all CMS regulations and Healthfirst marketing guidelines.
  • Ensure all documentation is complete, comprehensive, clear, appropriately filled out including Application, Application Confirmation Form, Scope of Appointment and Application Submission Form, and Salesforce.
  • Provide competitive intelligence to management on any activities Healthfirst’s market competitors are engaging in: e.g. marketing approach, branding campaign, new designs or benefit changes.
  • Develop and present strategic and tactical business acquisition plans for implementation throughout the year.
  • Assist with corporate initiatives related to Medicare quality or STAR ratings- i.e. HRAs/FPL/MSP.
  • Successfully pass audit (educational and marketing) exams.
  • Additional duties as assigned.

Work Location

The Outside Sales Rep will work at locations they develop within their designated territory, or they may need to visit prospects’ homes.

Minimum Qualifications & Experience


  • High School Diploma or GED from an accredited institution
  • Experience in a health plan sales role in the New York City market with a record of consistently producing maximum results in a compliant manner
  • Ability to manage travel, time, and territory efficiently, including simultaneously monitoring multiple marketing locations
  • Ability to collaborate with internal stakeholders and support teams for cross-referral and joint promotions
  • Ability to use technology and tools including Salesforce and Tableau for prospect/member record keeping and lead management
  • Active participation in continued professional development activities
  • Ability to travel throughout the New York City area
  • Ability to work majority of time outside of HF offices with little direct supervision
  • Strong interpersonal and collaboration skills
  • Must have good organizational skills
  • Ability to communicate effectively orally and in writing
  • Must have a valid and unexpired NY Health & Accident License

Preferred Qualifications


  • Proof of valid driver’s license and insurance
  • Associates or Bachelor’s degree from an accredited institution
  • Bi-lingual a plus



Hiring Range*:



  • Greater New York City Area (NY, NJ, CT residents): $68,900 - $99,620
  • All Other Locations (within approved locations): $61,300 - $91,120

As a candidate for this position, your salary and related elements of compensation will be contingent upon your work experience, education, licenses and certifications, and any other factors Healthfirst deems pertinent to the hiring decision.

In addition to your salary, Healthfirst offers employees a full range of benefits such as, medical, dental and vision coverage, incentive and recognition programs, life insurance, and 401k contributions (all benefits are subject to eligibility requirements). Healthfirst believes in providing a competitive compensation and benefits package wherever its employees work and live.

  • The hiring range is defined as the lowest and highest salaries that Healthfirst in “good faith” would pay to a new hire, or for a job promotion, or transfer into this role.

Salary : $61,300 - $91,120

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