Medical Telesales Representative Jobs (NOW HIRING)

Westgate Resorts is the largest privately held timeshare company in the world, with 60+ resorts in top destinations like Orlando, Las Vegas, Gatlinburg, Park City, and Myrtle Beach. Recognized by U.S. News & World Report as one of the Best Companies to Work For, we're committed to creating a supportive, rewarding workplace where our 9,000 Team Members can grow and thrive. Since 1982, we've delivered unforgettable vacations through exceptional service, innovation, and community engagement. With the recent addition of VI Resorts by Westgate, our footprint now includes the Pacific Northwest, Hawaii, Canada, and Mexico. Join us and be part of a team that values passion, integrity, and excellence, where your work helps create memories that last a lifetime.

Pay: $14.00 vs. commission whichever one is greater - Access your earned income instantly and manage your money with free financial wellness tools through DailyPay.

As a Telesales Representative, you'll help former owners rediscover the value of vacation ownership. You'll guide them through a sales process, listen with empathy, and match them with the right product at the right price. This role offers a steady income, biweekly pay, benefits, and the chance to build lasting relationships while driving revenue for Westgate.

What You'll Do:

• Make outbound/receive inbound calls to past owners to generate new sales, and upgrades to restructure their accounts.
• Re-engage canceled owners by understanding concerns, overcoming objections, and offering tailored product solutions.
• Manage leads over a 45-day sales cycle with consistent follow-up (calls, emails, texts).
• Present the full Westgate product portfolio (cross-trained across all inventory).
• Ensure customer satisfaction by confirming products sold meet needs and expectations.
• Achieve department standards:
  • 50+ calls daily
  • $40,000+ average net volume
• Accurately document all interactions and follow company/regulatory policies.
• Partner effectively with Telesales Team lead who is organizing and assigning leads.

To perform this job successfully, an individual must be able to perform each essential duty satisfactorily. The requirements listed below represent the knowledge, skills, and abilities required for the position. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

What You'll Bring:

• Active Florida Real Estate License (required).
• 6+ months timeshare sales experience preferred.
• High school diploma or GED.
• Strong communication and objection-handling skills.
• Organized, self-motivated, and goal oriented.
• Basic computer and CRM proficiency.

Why Westgate?  

• Comprehensive Health Benefits - Medical, Dental, and Vision Coverage
• Paid Time Off - Vacation, Sick, and Personal Time to Recharge
• Paid Holidays
• 401(k) with Generous Company Match to Support Your Future
• Daily Pay - Access Your Earnings When You Need Them
• Family-Focused Benefits - Pregnancy, Parental Leave, and Adoption Assistance
• Wellness Programs to Support Your Well-Being
• Flexible Spending Accounts (FSA)
• Tuition Assistance to Help You Grow Your Career
• Military Leave
• Employee Assistance Program (EAP) - Support When You Need It Most
• Life, Disability, Accident, Critical Illness, and Hospital Insurance
• Pet Insurance for Your Furry Family Members
• Loyalty Program - Exclusive Discounts on Hotels, Cruises, Resorts, Restaurants, Entertainment, and More
• Low-Cost Gym Membership
• NEW! David A. Siegel Legacy Scholarship - Up to $40,000 for Team Members' Dependents
• Career Growth and Advancement Opportunities
• Community Involvement - Give Back and Make an Impact

Westgate Resorts is an Equal Employment Opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, protected veteran status, disability status or any other protected status under federal, state or local law. If you have a disability and believe you need a reasonable accommodation in order to complete your application or any part of the recruiting process, please email [email protected] with the job title and the location of the position for which you are applying.

This job posting is intended to provide a general overview of the position and may not include every responsibility, duty, or qualification required. Duties, responsibilities, and activities may change at any time with or without notice.