Senior IT Sales / Account Manager

Cayman Islands

Grand Cayman is one the world’s most recognized offshore financial centers and home to thousands of expat workers taking advantage of unique career opportunities within a TAX FREE jurisdiction… all while enjoying a Caribbean Island lifestyle!

On behalf of our client, a premier MSP and provider of IT solutions and professional services in the Cayman Islands, we are searching for proven and highly mobile IT Sales Professional who would have interest in relocating to join their well established staff team in Grand Cayman.

The role is anticipated to include a mix of new business development and account management/growth of existing client accounts both within Cayman and the surrounding English speaking Caribbean region. Industry verticals include Financial Services (Offshore Banking, Investment, Accounting), Legal, Government, Hospitality and more.

We’re looking for the following:

  • Proven success and experience in an IT solutions sales role with a VAR, MSP or IT Consultancy
  • Proven success in proposing and selling IT services and contracts (including Professional Services, Managed Services, IT Security Services, Projects, Cloud Services, Office 365 etc.) and Enterprise Infrastructure Solutions (such as Servers, Storage, Microsoft Technologies, VMware, Backup, Wireless and Wired Networking etc.)
  • Proven ability to engage with and effectively manage relationships at the C-level, business and IT decision maker levels – preferably with experience selling to the financial services sector
  • Industry sales training and vendor sales/technical certifications would be an advantage (e.g. Microsoft, Cisco, VMWare, HPE, DELL, EMC, 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 with the ability to adapt well to this unique business market and island living environment.

A tax-free compensation package (base plus uncapped commission plan) will be offered to the successful candidate. Relevant work permit, relocation cost assistance, initial temporary housing and other benefits will be available.

Last update: December 1, 2021

Please apply or contact:

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