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Licensed Medicare Sales Representative

$26 per hour

Tailored Management

Sales (IC) Senior Associate

Fully remote in any state except CA, NY, AK, or HI

Monday-Friday, standard shifts are anywhere between 7am 10pm CST, 7 days a week, and are subject to change based on staffing needs.

08/31/2026, pending completion of new hire onboarding

3 months (opportunity for extension or conversion to FTE, depending on performance, attendance, and business needs).

Health, Dental, Vision

$26.00/hr (paid weekly)

Responsibilities:

  • Achieve and exceed assigned sales targets by consistently delivering high-quality sales presentations, positioning and closing sales.
  • Handle inbound calls, outbound calls and chat leads to support business needs as necessary.
  • Leverage artificial intelligence to guide conversations and conduct needs analysis using consultative selling skills.
  • Adhere to CMS and company compliance quality standards.
  • Responsible for positioning all Medicare solutions based on the needs assessment to include Medicare Advantage, Medicare Supplement, Prescription Drug Plan, Dental and Ancillary products.
  • Flexible, ability to pivot to support business needs as necessary.
  • Develop and maintain a robust sales pipeline by actively prospecting for all Medicare products and following up on leads.
  • Participate in special projects as required for the business.
  • Adhere to a rotating schedule of inbound and outbound times to maximize sales conversion.

Skills:

  • Proficiency in using CRM systems (e.g. Salesforce) and navigate other sales and telephony tools.
  • Experience with Microsoft Office products such as Excel and Outlook and ability to type 50-60 WPM.
  • Experience with technology to include high level use of laptops, camera and desk phones.
  • Exceptional communication and interpersonal skills, with the ability to build rapport quickly and effectively with customers.
  • Open to receiving constructive feedback and coaching.
  • Self-motivated, goal oriented, and capable of working independently or as part of a team.
  • Excellent organizational skills and ability to manage multiple tasks and priorities effectively.
  • Ability to adapt in a fast-paced environment.

Qualifications:

  • Maintain an active Health, Accident & (Life preferred) resident license.
  • Bachelors preferred.
  • Minimum of 2 years of direct-to-consumer sales experience.
  • Proven track record of achieving and exceeding sales targets.
  • Cable broadband or Fiber Optic with internet speeds of at least 10 Mbps download and 5 Mbps upload.
  • Must be able to attend the entire duration of training.
  • Able to work weekends, holidays, evenings, and rotating shifts. Standard shifts are anywhere between 7am 10pm CST, 7 days a week, and are subject to change based on staffing needs.
  • Ability to work OT as business requires.
  • Bilingual candidates are encouraged to apply.
Tailored Management
Vacancy posted 4 days ago
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