Senior System Engineer - work in the Cayman Islands! TAX FREE!

JR United Kingdom; London; On-site; USD 70,000 - 100,000; Full time

Job summary

A leading company is seeking a Senior Systems Engineer to manage IT operations in Grand Cayman. This hands-on role involves overseeing IT infrastructure performance and security while offering the unique opportunity to enjoy a Caribbean lifestyle. Ideal candidates will have extensive experience with Microsoft, VMware, and Cisco, and hold relevant certifications.

Benefits

TAX-FREE compensation

Relocation cost assistance

Work permit application support

Qualifications

• 10+ years of professional IT experience.
• Expertise in Windows Server, Cisco, VMware.
• Experience in retail POS systems preferred.

Responsibilities

• Manage IT performance, security, and support.
• Lead role in systems planning, configuration, and maintenance.
• Supervise support staff and third-party services.

Skills

Microsoft 365

VMware

Cisco networking

Cyber Security

End-user support

Education

Microsoft certifications

VMware VCP certification

Cisco CCNA certification

ITIL or CISSP certifications

Job description

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Senior System Engineer - work in the Cayman Islands! TAX FREE!, london

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Client:

Squires Partners Inc.

Location:

london, United Kingdom

Job Category:

Other

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EU work permit required:

Yes

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Job Views:

2

Posted:

24.06.2025

Expiry Date:

08.08.2025

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Job Description:

Senior Systems Engineer (IT Manager) - relocate to work in the Cayman Islands!

Have you considered putting your IT systems management and support background to use internationally?

We are seeking a motivated IT professional with current industry certifications across Microsoft, VMware, and Cisco (at minimum), who would enjoy relocating to join our client’s retail-focused business in sunny, tax-free Grand Cayman!

Role overview:

Reporting to the organization's CFO, and acting in a fully hands-on capacity as the lead/primary internal IT resource, the IT Manager/Senior Systems Engineer will be responsible for the overall performance, security and resiliency of all infrastructure, hardware and software applications utilized by a large retail location and a related entity on island.

The post holder will assume a lead role in systems planning, design, procurement, installation, configuration, monitoring, maintenance, security, documentation and support of the full IT environment.

This is an entirely hands-on role, managing everything IT for the organization in a hands-on capacity while supervising the work of one support analyst and a 3rd party MSP when needed.

We are looking for someone who is highly mobile and motivated by the opportunity to enjoy the unique lifestyle change that living and working in the Cayman Islands will afford.

Required experience and qualifications:

• A minimum of 10 years professional experience covering a diverse range of areas including (as many as possible of) Windows Server, M365, VMware, Cisco networking, Connectivity and Telephony, Firewalls, Storage, Backup/DR systems, Cyber Security, Desktop/workstations, and End-user support.
• Additional experience supporting retail POS systems, Financial Accounting software, Timekeeping devices, multi-function IP Printers, Building Management and Security (IP CCTV, Fire/Security Systems, Lighting controls etc.) would be an advantage.

Current industry certifications are required and highly valued:

• Microsoft certification(s) are required: Windows Server (Server 2016 or newer), Microsoft 365, Exchange, Windows 10/11
• VMware certification is required: VCP 2023 or newer
• Cisco certification is required: CCNA at minimum, CCNP is preferred
• ITIL and/or CISSP or similar would be a strong advantage - or willingness to pursue (employer supported)

This is a full-time/employee position based onsite in George Town, Grand Cayman. Due to the international move and immigration process involved, our client is looking for a highly mobile candidate, who will be able to relocate easily/relatively quickly with few complications.

Our client offers the rare chance to enjoy a Caribbean lifestyle while continuing in your professional career and earning competitive, TAX-FREE compensation. Relevant work permit application, relocation cost assistance and a range of additional benefits will be offered.

If you have relevant experience and valid certifications in the above areas and are interested in the prospect of living and working in Grand Cayman, please apply and/or contact Jason Squires for a casual and confidential conversation.