We are currently seeking entry level and/or experienced Inside Sales Representatives to join our team. Sales Agents will assist customers in making Medicare healthcare decisions by carefully matching customers with the optimal products and services. This person will be responsible for maintaining the highest level of professionalism and providing a great customer experience to all customers, while consistently meeting and/or exceeding monthly sales goals. This position will report to Medicare Sales management.


  • Drive sales and revenue by assisting customers in making healthcare decisions over the phone.
  • Meet monthly sales and performance goals.
  • Ability to close transactional sales.
  • Successfully completing our comprehensive sales representative training which includes product knowledge, salesmanship, and our software systems
  • Basic phone sales skills.
  • Remain current on products and processes in a multi-product environment.
  • Abide by the Centers for Medicare and Medicaid Services (CMS) Medicare Marketing Guidelines and company policies and procedures.
  • Consistently attain monthly sales goals.
  • Make outbound telephone calls to follow up on and close business.
  • Other duties and projects will be assigned as needed.


  • 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.
  • Flexible in hours you are able to work (possible nights and/or weekends).


LendingTree is the nation’s largest online lending marketplace. That means we connect customers with multiple lenders so they find the best deals on loans, credit cards, savings accounts and insurance. Our goal is to help people save money, and we believe the best way to do that is by giving them a way to shop for loans and compare lenders so they make their best financial choices.
Our CEO Doug Lebda founded the company in 1996 after a frustrating house-hunting experience. In those days, we mostly helped people find good mortgage deals. Now, we help consumers find their best in personal loans, auto loans, business loans, student loans, credit cards, savings accounts, home equity loans and more.
What else you should know: 
  • 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!

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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