The Medicare Sales Trainer will develop and deliver sales specific training programs to new and existing Medicare sales agents in an effort to increase call center sales production and efficiency. The Medicare Sales Trainer is responsible for creating and presenting effective Medicare sales trainings and sales techniques to agents in a classroom setting and in one-on-one/small group trainings.

Our ideal candidate is a "Sales Guru" with past Medicare sales experience, a fun and magnetic personality and the ability to motivate call center sales teams to top performance. The Medicare Sales Trainer will work closely with the call center sales teams to identify opportunities for continued sales trainings, curriculum training, product trainings and sales process trainings. Responsibilities will include revising current sales training materials, creating original sales training content and curriculum, and providing reports and summaries to back up training techniques.  In addition, the Medicare Sales Trainer will be responsible for ensuring all agents are following current Quality Monitoring guidelines and standards that CMS and Insurance carriers require. 

Essential Duties and Responsibilities:

  • Executing creative, interactive and exciting medicare sales training programs to reinforce education related to sales and retention
  • Build rapport quickly and motivate individuals to meet specific goals
  • Effectively deliver Medicare Sales training to new managers and new agents in the classroom and on the sales floor
  • Coach and provide feedback to agents to increase sales performance
  • Effectively drive agent development via classroom training sessions, mentorship/coaching, floor supervision, etc.
  • Assess agent effectiveness through reporting, call monitoring, sales metrics, and initiatives, and deliver training sessions to maximize sales production.
  • Processing and reviewing team member performance, identifying knowledge gaps and organizing subsequent training appropriate to close those gaps
  • Motivating and encouraging sales team members to think creatively and collaborate to success
  • Assess agent effectiveness by ensuring they are following all compliance standards set forth by CMS and Insurance carriers
  • Manage the training and license process to unlicensed sales agents


  • Sales training experience and deep understanding of the sales process and tactics REQUIRED
  • Must be energetic, work well under pressure and be able to manage shifting priorities
  • Prior experience in Medicare sales highly desired
  • Demonstrated ability to drive and lead company sales programs/initiatives.
  • Demonstrated ability to mentor and develop Sales Managers and sales teams
  • Proficiency in coaching and facilitator skills
  • Strong work ethic and ability to work effectively with little direct supervision.
  • Solid presentation and written/verbal communication skills
  • Working knowledge of Microsoft Office software. Ability to instruct on computer enrollment technology, CRM database system and Internet applications

What You’ll Love About Our Company

  • Medical, dental and vision coverage, starting your first day of employment.
  • 401k plan with company match.
  • All employees are awarded Restricted Stock Units
  • Wellness Programs
  • Paid training, including licensing course.
  • PTO accrual starting day one.


QuoteWizard, a LendingTree company, is a dynamic insurance lead generation agency based in Seattle. We have been ranked by the INC 500 as one of the fastest growing private companies in the nation. We have also been listed by the Puget Sound Business Journal as a top company in Seattle.

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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