Systems Support Engineer

Cayman Islands

Here’s your chance to join a strong team of local and international expatriate staff blending the best of career and lifestyle in this sophisticated, offshore financial environment. When your workday is finished, take advantage of all that Grand Cayman has to offer including beautiful beaches, scuba diving, snorkeling, boating, fishing, high quality dining and much more!

We are searching for an experienced and highly mobile IT professional to join our client, an award winning provider of IT solutions and managed services in the Cayman Islands.

The successful candidate will be a part of a customer-facing team working to deliver and support the information technology needs of a cross section of client organizations in Grand Cayman and the Caribbean region.

Day to day workload will vary depending on client needs but expected to include a mix of implementation tasks and support of existing solutions involving on-site, remote and service desk support in response to incoming support tickets.

We are looking for the following background in an ideal candidate:

  • Minimum of 3 years of professional experience providing customer-facing IT support services with an IT consultancy, MSP, VAR or similar service provider organization
  • Proven ability to successfully troubleshoot and solve customer issues taking ownership of support tickets and seeing through to resolution
  • Broad general support experience that covers (as many as possible of): Windows Server, Active Directory, Exchange, Windows Desktop, Azure, Office 365, Cisco, Fortinet, HPE Hardware, Veeam
  • Prior service desk experience would be an asset
  • A customer service oriented approach with strong communication and interpersonal skills


Qualifications required:

  • Current industry certification(s) from Microsoft and complimentary technical areas above are required and will be highly valued
  • Post secondary degree or diploma in a relevant field preferred


This is a full-time, employee position based in Grand Cayman. Due to the relocation involved, candidates should be highly mobile, adaptable and able to make a long-term move to Grand Cayman.

What’s on offer?

The chance to pursue a life changing move, gain international experience in an offshore financial setting and enjoy the idyllic Island lifestyle offered … while taking advantage of the TAX FREE status!

Compensation will be competitive, commensurate with qualifications and experience. Work permit application, health insurance, pension, relocation cost assistance and other benefits will also be offered.

Last update: February 14, 2020

Please apply or contact:

Jason Squires
1-705-725-7663
jason@squiresresources.com