Senior Technology Lead - Caribe Royale Orlando Hotel

Caribe Royale • Orlando, FL

6h

About The Position

The Senior Technology Lead is responsible for overseeing and supporting enterprise IT infrastructure, property management systems, Point of Sale (POS) platforms, Digital Signage environments, and end-user computing systems. This role requires deep expertise in Microsoft Active Directory, M365, Servers, Networking, Printers and desktop/laptop environments. Experience with Point-of-Sale systems (Toast preferred) is strongly desired. The ideal candidate is a hands-on technical leader who can architect, implement, and support complex systems while mentoring team members and ensuring operational excellence across multiple business units.

Requirements

• Professional demeanor appropriate for a resort environment.
• Minimum 6 years of progressive IT experience, with 3+ years in a senior or lead role.
• Advanced expertise in Microsoft Active Directory administration.
• Strong experience supporting Point of Sale (POS) systems (Toast preferred).
• Solid understanding of Digital Signage systems and endpoint management.
• Strong networking knowledge (TCP/IP, DNS, DHCP, firewalls, switching, wireless).
• Experience with Windows Server environments.
• Expert-level desktop/laptop troubleshooting and deployment skills.
• Strong documentation and communication skills.
• Ability to communicate effectively in English, a second language, is a plus.
• Excellent administrative, interpersonal, organizational, and communication skills.
• Strong problem-solving and analytical abilities.
• Ability to create and maintain spreadsheets.
• Ability to meet deadlines and work under pressure.
• Ability to work with minimal supervision and manage multiple tasks.
• Ability to work flexible schedules, including holidays and weekends.
• Must be physically fit to lift, pull, and push items up to 50 pounds.

Nice To Haves

• Understanding networks and hotel applications is an asset.
• High school diploma or equivalent; experience in a large hotel environment preferred.
• Minimum of 2 years' experience in information technology or a related field.

Responsibilities

• Design, manage and optimize Microsoft Active Directory environments (user provisioning, Group Policy, security policies, domain services).
• Deploy, manage, and troubleshoot Point of Sale (POS) systems (Toast preferred).
• Oversee Digital Signage systems, including content distribution, endpoint management, and display hardware support.
• Maintain Windows server environments, file services, and related infrastructure components.
• Configure and support LAN/WAN environments, including VLANs, firewalls, VPNs, and wireless infrastructure.
• Monitor network performance, ensure uptime, and troubleshoot connectivity issues.
• Collaborate with vendors and ISPs to maintain reliable connectivity across locations.
• Provide expert-level support for desktops, laptops, and mobile devices (Windows and macOS).
• Lead hardware lifecycle management, imaging, deployment, and patch management.
• Develop and maintain endpoint security standards.
• Lead technology implementations, upgrades, and migrations.
• Coordinate with third-party vendors for PMS, POS, networking, and signage solutions.
• Document processes, configurations, and system architecture.
• Ensure systems comply with security, compliance, and operational standards.
• Develop IT roadmaps aligned with business objectives.
• Maintain high service levels and continuous improvement initiatives.
• Perform any other duties as required by management.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: High school or GED