Benefits Representative

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.

Westgate Resorts is hiring a full-time Benefits Representative for our corporate office in Ocoee, FL. As a Benefits Representative, you will be responsible for benefits administration, data entry, problem resolution, and team member support across multiple systems including ADP, PlanSource, Lawson, and TransAmerica. You will help ensure team members understand their benefits, resolve issues quickly, and receive accurate and timely service.

In this role, you will partner with HRIS, Payroll, Field HR, and external benefits providers to verify eligibility, audit updates, correct discrepancies, and maintain compliance with federal and state regulations. Your daily work will include reviewing CSD tickets, processing HRIS-driven changes, preparing benefit letters, communicating with team members, and completing enrollment updates. You will also support open enrollment coordination, wellness initiatives, and reporting responsibilities. Because this is an on-site role in Ocoee, Florida, you will collaborate closely with your team in a corporate office environment.

• Review CSD tickets and incoming emails daily to ensure timely resolution.
• Process HRIS updates and adjust benefit records in ADP and PlanSource.
• Conduct benefit audits, verify premiums due, correct discrepancies, and submit payroll adjustments.
• Prepare dependent eligibility and verification letters for team members via local HR.
• Complete data entry in PlanSource and maintain accurate records.
• Explain benefit programs including health, dental, life, 401k, Accident & Critical Illness, and disability plans.
• Prepare written responses to team members, HR, and outside agencies.
• Assist with creating internal processes and procedures for HR and benefits teams.
• Research and resolve provider issues related to coverage, billing, and ID cards.
• Review benefit provider reports to verify accuracy.
• Remind team members of eligibility deadlines, open enrollment periods, and wellness program requirements.
• Process benefits enrollment and required documentation.
• Resolve team member billing or overcharge issues.
• Research and adjust time accrual discrepancies.
• Process QDROs and prepare written responses to courts.
• Gather documents for subpoenas related to benefits.
• Review Evidence of Insurability submissions for accuracy.
• Maintain tracking systems for follow-ups.
• Prepare billing for team members on leave and forward payments to Cash Management.
• Process monthly benefits billing and ensure scans into ImageQuest.
• Answer Benefits Service Center calls, create CSD tickets, and resolve issues.
• Coordinate coverage questionnaires from agencies to verification providers.
• Assist with open enrollment scheduling, communication materials, and 401k meetings.
• Use intermediate Excel skills (pivot tables, VLOOKUP).
• Upload 401k deferrals and coordinate files with the Las Vegas team.
• Support Wellness Committee communications and challenges.

• High School diploma or equivalent required.
• Certificate in Benefits or HR Administration preferred.
• 3–6 months of HR, benefits, or administrative experience required; benefits experience preferred.
• Strong customer service and communication skills.
• Ability to manage multiple tasks, heavy workloads, and deadlines.
• Proficiency in Microsoft Excel and Word; intermediate Excel required.
• Experience with ADP, PlanSource, or similar HRIS/benefits systems preferred.
• Detail-oriented, self-motivated, and able to work independently.
• Multilingual abilities a plus.

Why Westgate?

• Comprehensive health benefits – medical, dental and vision
• Paid Time Off (PTO) – vacation, sick, and personal
• Paid Holidays
• 401K with generous company match
• Get access to your pay as you need it with our Daily Pay benefit
• Family benefits including pregnancy, and parental leave and adoption assistance
• Wellness Programs
• Flexible Spending Accounts
• Tuition Assistance
• Military Leave
• Employee Assistance Program (EAP)
• Life, Disability, Accident, Critical Illness & Hospital Insurance
• Pet Insurance
• Exclusive discounts for Team Member (i.e., hotels, cruise, resorts, restaurants, entertainment, etc.) 
• Advancement & development opportunities
• Community Involvement Programs

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.