Benefits Representative

Westgate Resorts • Ocoee, FL

2d • $21

About The Position

As a Benefits Representative at Westgate Resorts, you’ll be a friendly and knowledgeable resource for team members navigating their benefits. Reporting to the Benefits Manager, you’ll support day-to-day benefits administration, help resolve questions, process updates, and ensure information is accurately entered across our systems (ADP, PlanSource, TransAmerica, and Lawson). This role is a great fit for someone who enjoys customer service, problem-solving, learning HR systems, and contributing to a positive team member experience. You’ll gain hands-on exposure to benefits administration, HR operations, payroll coordination, and compliance, offering a strong foundation for growing your HR career within a leading hospitality company.

Requirements

• Proficient computer and P/C skills; experience with Microsoft Word and Excel
• Strong customer service and communication skills
• Detail-oriented, self-motivated, and able to follow tasks through with limited supervision
• Ability to multitask and manage a steady workload
• High School diploma or equivalent required
• One-year certificate in Benefits or HR Administration OR 3–6 months related experience/training OR equivalent combination of education and experience
• General computer accuracy and comfort with HRIS/benefits platforms preferred

Nice To Haves

• Multilingual a plus
• Experience with ADP, PlanSource, or similar benefit systems preferred

Responsibilities

• Respond to CSD tickets, emails, and phone inquiries to resolve team member benefit questions
• Process HRIS updates and make required benefit changes (rehire, transfer, pay/status changes) in ADP and PlanSource
• Assist with benefit enrollment support, data entry, documentation review, and dependent verification.
• Conduct basic audits for premium discrepancies and submit corrections to Payroll
• Help team members understand available benefits (401(k), health, life, supplemental plans, wellness programs, etc.)
• Investigate and resolve common issues such as coverage levels, ID card problems, and billing discrepancies
• Prepare and distribute benefit letters, notifications, and reminders for eligibility, lifestyle events, and open enrollment
• Maintain organized benefit records, including scanning documents into ImageQuest
• Process monthly billing, track payments for team members on leave, and coordinate with Payroll and Cash Management
• Upload 401(k) files and assist with wellness communications and committee activities
• Support open enrollment scheduling and benefit education materials with local HR

Benefits

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level
• Education Level: High school or GED
• Number of Employees: 5,001-10,000 employees