The Medicare Sales Supervisor is responsible for achieving results by providing frontline leadership, management and coaching to a team of telesales agents who are responsible for enrolling consumer prospect into Medicare Senior plans. Responsibilities include motivation, resource management, coaching and training of staff. This position reports to the Director of Medicare Sales.


  • Mentor and motivate agents to achieve or exceed sales targets with a focus on quality and compliance
  • Supervise the daily activities of the team by reviewing and analyzing calls/reports, assessing areas of opportunity, managing work assignments and assuring agents are providing a positive consumer experience
  • Develop staff by providing one-on-one coaching, conducting role plays and team meetings
  • Partner to deliver training and other opportunities of professional development for agents
  • Partner with peer leaders to build and maintain a positive culture within the organization.
  • Provide and receive constructive feedback from/to peer leadership team
  • Coordinate department activities to ensure agents can sell with accuracy and efficiency
  • Partner with other leaders in the organization to evaluate, coordinate and communicate changes with your team.
  • Identify compliance and quality improvements and initiate corrective actions
  • Partner on projects related to systems, processes or inter-department initiatives
  • Participate in staff recruiting, selection, orientation and training
  • Identify issues, training needs and develop and maintain processes within the department
  • Perform other related duties as required to achieve the goals and objectives of the company and department
  • Abide by the Centers for Medicare and Medicaid Services (CMS) Medicare Marketing Guidelines and company policies and procedures.
  • Other duties and projects will be assigned as needed.


  • Leadership experience in a production or call center environment
  • Will ideally possess 2+ years industry experience in: a broker or insurance company, Medicare and/or individual sales environment, with a successful track record of goal achievement.
  • Knowledgeable in CMS and Health Care reform rules and regulations.
  • Experience selling senior insurance products via the telephone a plus.
  • Inside sales experience.
  • Excellent computer software skills, i.e. Word, Excel, Internet skills.
  • Excellent oral and written communication skills.
  • Health Insurance license preferred.
  • Prefer BA/BS; High School Diploma required.
  • Selling via Internet channel background a plus.
  • Call center experience a plus.
  • Must be flexible in hours you are able to work (possible nights and/or weekends).

NOTE: As a licensed position working within a regulated industry, all Medicare Representatives must undergo extensive background checks that will include criminal background and credit history reports. QuoteWizard may deny employment to or terminate the employment of any applicant or employee for whom the results of the background checks prevent or adversely affect licensing or certification.


QuoteWizard, a LendingTree company, provides end-to-end solutions for insurance shoppers and agents alike. That’s why over 40 million people have used QuoteWizard to lower their rates. When you think of insurance, think of QuoteWizard.

What you should know about LendingTree, our parent company:

  • We’re a publicly-traded company (TREE).
  • We’ve welcomed several other companies into the LendingTree family to augment our efforts at helping borrowers make their most sensible financial choices.
  • We’ve built the LendingTree app and My LendingTree dashboard to give consumers tools to manage and monitor their financial health.
  • We still make funny commercials.


We’re a fast-paced company with an entrepreneurial bend. We work hard and test our products often. We’re collaborative, ambitious, candid and high-energy. Our teammates are some of the brightest, most talented people you’ll ever work with. We care more about your smarts than we do about the kinds of clothes you wear (but please, do wear clothes to work!), and we’re pretty good about rewarding innovation, creativity and the knack for just getting stuff done (we even have an award for employees called the GSD, “Get Stuff Done”).

Come work with us!

QuoteWizard by LendingTree is the kind of company that not only promotes diversity and inclusion; we thrive because of these values. We do not discriminate based on race, color, religion (or creed), gender, gender expression, age, national origin, disability, marital status, sexual orientation or military status.


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