IT Technician

JOB DESCRIPTION

Tortuga Rum Company is seeking a skilled IT Technician to support the IT Manager in delivering reliable, secure technology across the business. The role covers our corporate office, retail locations, and bonded warehouses throughout Grand Cayman and Cayman Brac.

The successful candidate will provide first-line technical support, maintain point-of-sale and network infrastructure, and contribute to IT projects. This is a hands-on, multi-site role suited to a proactive professional who takes ownership of issues through to resolution.

KEY DUTIES & RESPONSIBILITIES

Be the first point of contact for IT support by phone, email and in person, logging and resolving tickets within agreed service levels.

Diagnose and fix hardware, software, peripheral and mobile device issues.

Manage user accounts and access in Active Directory, Microsoft Entra ID and Microsoft 365, and set up IT for new starters and leavers.

Install, configure and maintain POS workstations across our retail stores, and keep item, pricing and inventory data up to date in Counterpoint.

Install, terminate, test and label structured data cabling, and keep network documentation accurate.

Apply patches and firmware updates, and support server maintenance, backups and restores.

Install and repair telephony and telecommunications equipment.

Set up and deploy laptops, workstations, POS stations and mobile devices, and keep the IT asset register up to date.

Support IT projects, system rollouts and testing, and look for ways to improve how we work

QUALIFICATION & REQUIREMENTS

At least 3 years' experience in IT support, helpdesk or a technician role.

Industry certifications such as CompTIA A+, CompTIA Network+, Fortinet FCP – Network Security or Microsoft 365 Endpoint Administrator Associate.

Strong hands-on skills with Windows, Microsoft 365, TCP/IP networking, hardware and peripherals.

Proven experience installing, terminating and testing structured data cabling.

Experience with NCR Counterpoint or a similar retail POS system, ideally in a multi-site retail or hospitality setting.

Working knowledge of Microsoft Intune or Configuration Manager (SCCM).

Experience using a service desk or ticketing system, with good documentation habits.

Excellent communication and customer service skills, including with non-technical users.

The ability to work independently, juggle priorities and meet deadlines.

Confidence using AI tools responsibly to support troubleshooting, documentation and automation.

Integrity and care with company equipment and confidential information.

A high school diploma or equivalent.

A valid driver's license and reliable transport for travel between sites.

BENEFITS: Health Insurance, Pension, Vacation & Sick leave as required by the Cayman Islands Law

We welcome suitably qualified Caymanians and Legal Residents to apply