Sales Executive, IT Services & Solutions

Cayman Islands

We are searching for an experienced – and highly mobile – IT Sales professional in a position to relocate and join our client, an award-winning MSP and provider of IT solutions and services in the Cayman Islands.

This will be a truly unique opportunity for the right person/at the right time to enjoy a total change of scenery while continuing their successful IT Sales career. Cayman is home to a large number of International Expats who have chosen to make the island their home away from home.

The role will be primarily focused on the acquisition of new customers within the Cayman Islands and Caribbean. The position will be well suited to an experienced hunter who enjoys developing new business relationships and has direct IT solutions and IT services sales background. 

We are looking for the following:

  • Minimum 5 years of proven success in an IT sales role with an MSP, IT Consultancy or similar
  • Knowledge of /past experience selling as many as possible of: Servers and Storage products, Networking, Microsoft 365, Backup solutions, IT security, Virtualization, Hyper converged solutions and “as a Service” models. 
  • Experience selling services (Professional and Managed Services)
  • Proven ability to engage with and effectively build customer relationships (C-level and IT decision maker levels). Experience selling to the financial services sector would be an asset
  • Proven ability to drive the entire sales cycle from initial customer engagement to closed sale
  • Industry sales training and vendor sales/technical certifications would be an advantage (e.g. Microsoft, Cisco, VMWare, HPE, Fortinet, Aruba etc.)
  • College or University education preferred


This is a full-time role based in Grand Cayman. We are therefore looking for someone able to relocate relatively easily and with the ability to adapt to this unique business market and living environment.

A TAX FREE compensation package (base salary plus uncapped commission plan, car allowance and more) will reward the post holder for successful performance.

Relevant work permit, relocation assistance, health insurance and other benefits will also be offered.

Last update: September 27, 2023

Please apply or contact:

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