IT Manager (relocate to the Cayman Islands!)

Information Technology Manager – Cayman Islands

Approx. $CAD 140,000 - $170,000 equivalent, with no income tax deductions.

Local salary range: CI$ 80,000 - 100,000 (Cayman Islands dollars)

If you’re an experienced and currently hands‑on IT infrastructure professional who is open to exploring a move to the Caribbean, we’d love to speak with you about a full‑time opportunity with an established organization in the sunny, tax‑free Cayman Islands, supporting its primary retail operation and related businesses.

This is very much a hands‑on technical role , with the focus on technology, not staff management. Reporting to the CFO and serving as the organization’s primary internal IT resource, the IT Manager will be responsible for the overall performance, security and resiliency of the company’s technology environment.

The ideal candidate will be someone who enjoys remaining technically hands‑on – administering systems, troubleshooting problems, planning and delivering projects and upgrades, and taking ownership when something needs attention – while also coordinating with third‑party IT service providers when required. There is no dedicated internal IT support team, reflecting the hands‑on nature of the position.

The technology environment is primarily Microsoft and VMware based and includes Windows Server, Microsoft 365, hybrid Exchange, VMware ESXi/vSphere, Veeam backup and disaster recovery, Ubiquiti UniFi and Cisco networking, and Synology NAS, along with various systems and technologies required to support a large retail operation.

The role covers everything from core server and IT infrastructure through to networking, business applications, retail POS, end‑user systems and IP‑based security technologies. Some after‑hours and on‑call availability will also be required.

What we’re looking for

We’re looking for someone with a strong background in current, hands‑on systems administration and support across as much of the environment above as possible.

Strong practical experience with Windows Server, Microsoft 365, VMware and Exchange administration will be particularly important, ideally including experience supporting a hybrid Exchange/Microsoft 365 environment.

A relevant degree and current industry certifications are an important part of the requirement. We are particularly interested in candidates who hold current Microsoft certifications covering Windows Server and Microsoft 365, together with a current VMware certification. Microsoft Exchange certification would be an additional asset.

Relocating to the Cayman Islands

This is a permanent, full‑time position based on‑site in George Town, Grand Cayman. Beyond the role itself, this opportunity would suit someone genuinely interested in relocating to the Cayman Islands and who would enjoy the unique lifestyle, climate and quality of life Cayman has to offer.

Our client offers a competitive compensation package including a TAX-FREE salary , health insurance and pension benefits, along with ongoing training and certification support. Relocation assistance and an employer‑arranged work permit are also provided.

If the technical requirements sound like a good match and a move to the Cayman Islands is a practical consideration, we’d be very pleased to hear from you.