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IT Manager - Cayman Islands

Job in Ottawa, Ontario, Canada
Listing for: Squires Partners Inc.
Full Time position
Listed on 2026-10-30
Job specializations:
  • IT/Tech
    Systems Administrator, Windows Server, IT Infrastructure, Network Administrator
Salary/Wage Range or Industry Benchmark: 154000 - 224000 CAD Yearly CAD 154000.00 224000.00 YEAR
Job Description & How to Apply Below
Position: IT Manager - work in the Cayman Islands!
Information Technology Manager – Cayman Islands

Relocate to live and work in beautiful Grand Cayman!

Grand Cayman is home to a large international community, including many expatriates from Canada and around the world.

Competitive TAX-FREE Salary | Relocation Assistance | Caribbean Lifestyle

An established Cayman Islands organization is seeking an experienced, hands-on IT Manager to oversee the technology environment supporting its primary retail operation and related businesses.

Key Qualifications
  • VMware: VCP-DCV (or equivalent VMware certification)
  • Microsoft:
    Windows Server administration (AZ-800/AZ-801 or equivalent)
  • Microsoft Exchange:
    Additional certification or specialized training would be an asset

The ideal candidate is expected to have at least 10 years of hands-on systems administration and IT infrastructure experience, including strong practical experience with VMware, Windows Server, Microsoft 365 and Exchange.

The Role

Reporting to the CFO, this is a hands-on technical position focused on managing and supporting the organization's IT environment rather than managing a team.

The technology environment includes Windows Server, Active Directory, Microsoft 365, hybrid Exchange, VMware ESXi/vSphere, Veeam backup and disaster recovery, Ubiquiti Uni Fi and Cisco networking, Synology NAS, and various retail and business systems across several sites.

Responsibilities include day-to-day systems administration, troubleshooting, infrastructure upgrades, IT projects, security, backups, disaster recovery and coordination with external service providers. Some after-hours and on-call availability will be required.

Relocating to the Cayman Islands

This is a permanent, full-time position based on-site in George Town, Grand Cayman. Applicants should be genuinely interested in a move and in a position to relocate to the Cayman Islands with relative ease.

Our client offers a competitive TAX-FREE salary, health insurance, pension and other benefits, ongoing training and certification support, relocation assistance and an employer-arranged work permit.

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