Job Description

The Field Support Specialist is a hands-on, on-site technical lead responsible for installing, maintaining, and troubleshooting hardware, software, and networking infrastructure across supported properties. This role operates with minimal supervision, supports both staff and executives, and plays a key role in installations, upgrades, and incident resolution while meeting defined service levels.

What Will You Be Doing?

• Install, configure, troubleshoot, and maintain hardware, software, network devices, and structured cabling.
• Provide routine maintenance and basic configuration for network switches and infrastructure.
• Serve as lead support during installations, maintenance efforts, and high-impact incidents.
• Independently resolve issues; escalate critical problems appropriately to leadership.
• Build, image, deploy, and document devices and system configurations.
• Perform enterprise software deployments and updates.
• Support and administer endpoint/user management tools (Active Directory, Intune, SCCM, Tanium).
• Provide direct end-user support, including VPN and application assistance.
• Collaborate with Business Analysts, System Admins, and Project Managers on IT initiatives.
• Participate in on-call and after-hours support rotations.
• Travel up to 40% as required to support multiple locations.

Qualifications

Required Experience & Skills

• 3–5 years of hands-on field or technical support experience.
• Strong background in network switches, TCP/IP, VPNs, and basic networking infrastructure.
• Experience with Active Directory user and device management.
• Hands-on structured cabling support (identify, repair, test, document).
• Familiarity supporting POS systems or equivalent technologies.
• Experience supporting C-level executives.
• Strong troubleshooting, prioritization, and independent problem-solving skills.
• Proficiency with Windows 10/11 and a wide range of endpoint and AV devices.

Education & Certifications

• Bachelor’s degree in Computer Science or related field preferred.
• A+, Network+, or equivalent certification required.

Work Environment & Physical Requirements

• Frequent standing, walking, and on-site technical work.
• Must lift and move up to 50 pounds.
• Regular use of PCs and diagnostic tools.

Additional Information

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 WGAccommodations@wgresorts.com 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.