IT Solutions Sales Professional

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 provider of IT solutions in the Cayman Islands, we are searching for a proven IT Sales Professional to relocate and join their staff team in Grand Cayman.

This will be well-suited to a motivated, self-sufficient sales professional eager to grow relationships and close new business opportunities while being rewarded with uncapped earnings potential in this uniquely lucrative, TAX FREE environment.

The post holder will be responsible for prospecting, proposing and developing new business in areas including enterprise infrastructure solutions (such as servers, storage, networking, virtualization, IP networks, IP telephony and more), managed services, IT security, projects, professional services, support contracts and more. This will involve calling on and building relationships with a group of sophisticated corporate entities in the Cayman Islands and Caribbean region in verticals including investment, banking, accounting, legal, government, hospitality and more.


  • Minimum of 5 years of proven 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 (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.)

This is a full-time role based in Grand Cayman. We are 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 and uncapped commission heavy compensation model will be offered to the successful candidate. Package includes base salary plus commission, vehicle allowance and benefits including pension and health insurance contributions. 
Relevant work permit application, relocation cost assistance, initial temporary housing and car rental will also be provided.

Last update: February 1, 2021

Please apply or contact:

Jason Squires