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I.T. Support Specialist – POS Systems

Job in Orlando, Orange County, Florida, 32885, USA
Listing for: Jobtailor
Full Time position
Listed on 2026-07-20
Job specializations:
  • IT/Tech
    IT Support, Systems Administrator, HelpDesk/Support, Network Administrator
Salary/Wage Range or Industry Benchmark: 45000 - 60000 USD Yearly USD 45000.00 60000.00 YEAR
Job Description & How to Apply Below
  • Support and maintain the parks point‑of‑sale (POS) and guest transaction technology to keep daily operations running smoothly.
  • Troubleshoot POS hardware, software, and payment devices.
  • Support Windows endpoints and Microsoft 365.
  • Assist with basic network issues in a fast‑paced, live operational environment.
  • Opportunity to grow into systems administration/infrastructure paths.
  • Install, configure, and support POS terminals and peripherals (PIN pads, receipt printers, barcode scanners, cash drawers, tablets/mobile devices).
  • Troubleshoot POS software, payment processing issues, and device connectivity; perform firmware updates and maintenance.
  • Provide Tier 12 onsite and remote support for staff.
  • Respond to high‑priority outages and participate in weekend/on‑call rotation.
  • Administer and troubleshoot Windows environments, including basic Active Directory user/group support.
  • Support Microsoft 365 (mailboxes, licensing, Teams/SharePoint basics) and endpoint patching/AV updates.
  • Assist with basic network troubleshooting affecting POS (Wi‑Fi, VLANs, switches); support Meraki environments as needed.
  • Document incidents, procedures, and maintain asset/configuration records; support technology rollouts and upgrades.
Requirements
  • 4 years of IT support experience (retail/hospitality/POS experience strongly preferred)
  • Hands‑on experience supporting POS systems and payment devices; familiarity with PCI concepts a plus
  • Working knowledge of Windows, Active Directory, and Microsoft 365
  • Basic networking fundamentals (LAN/Wi‑Fi, DHCP, TCP/IP);
    Meraki experience a plus
  • Experience with ticketing and/or RMM tools (e.g., Ninja One or similar preferred)
  • Scripting/reporting exposure (Power Shell/batch/JavaScript and/or basic SQL) is a plus
  • Strong troubleshooting, customer service, and communication skills
  • Ability to work weekends/holidays and be part of an on‑call rotation; able to lift up to 40 lbs.
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