Tier 2 Systems Support Engineer (On-Site in Grand Cayman) at Cayman Solution Providers

About the position

?? Location: Grand Cayman, Cayman Islands
?? Employment Type: Full-Time, On-Site
?? Compensation: USD $[Phone Number Removed]; (experience dependent)
?? Benefits: Basic medical coverage, phone allowance, car allowance

About the Role
We're looking for a skilled Tier 2 Systems Support Engineer to join our growing Managed Services team in Grand Cayman.

This is a customer-facing, on-site position that requires relocation to the Cayman Islands. Please only apply if you are able and willing to relocate internationally.

You'll work directly with business clients across a wide range of industries, delivering high-quality technical support, managing system infrastructure, and performing on-site service visits when needed. If you enjoy problem-solving, working with cutting-edge Microsoft and virtualization technologies, and want to advance your career in a tropical setting, this role is for you.

What You'll Do
?? Microsoft 365 Administration

• Manage and secure Microsoft 365 tenants, focusing on Intune, Conditional Access, and Exchange Online
• Deploy and manage endpoint compliance and application policies
• Monitor alerts via Microsoft Defender and Security Center

?? Windows Server & Active Directory

• Maintain Active Directory, Group Policy, and DNS/DHCP
• Administer Windows Server and Hyper-V environments
• Manage domain joins, OU structure, and identity integrations

?? Virtualization & Backup

• Administer VMware ESXi and vCenter environments
• Manage backup and replication using Veeam Backup & Replication
• Conduct regular disaster recovery testing and verification

?? End-User & Desktop Support

• Provide advanced troubleshooting for Windows 10/11 systems and remote access
• Support user onboarding/offboarding and endpoint security
• Deliver professional, client-facing technical support, including on-site visits

?? MSP Operations

• Use RMM and ticketing systems to manage service requests and incidents
• Contribute to client documentation and proactive infrastructure maintenance
• Collaborate with cybersecurity and network teams to maintain service standards

What We're Looking For
? 5+ years of IT systems administration or support experience
? 2+ years working in an Outsourced or Managed Service Provider (MSP) environment
? Strong technical knowledge of:

• Microsoft 365 (Intune, Exchange, Conditional Access)
• Windows Server [Phone Number Removed];
• Active Directory, DNS, DHCP, Group Policy

? Experience with:

• Hyper-V virtualization
• VMware ESXi / vCenter
• Veeam Backup & Replication
• RMM tools, documentation systems, and ticketing platforms

? Relevant certifications (preferred):

• Microsoft Certified: Modern Desktop Administrator / Azure Administrator / M365 Certified, VMware VCP, or Veeam VMCE

Soft Skills
?? Excellent client communication and interpersonal skills
?? Strong analytical and troubleshooting ability
?? Customer-first attitude and professional presentation
?? Ability to multitask and manage competing priorities
?? Comfortable performing on-site client visits

Compensation & Benefits
?? Salary: USD $[Phone Number Removed]; (based on experience)
?? Benefits: Basic medical coverage
?? Phone allowance and ?? Car allowance included
?? Relocation required - on-site position based in Grand Cayman

If you're ready to take the next step in your IT career and work in a dynamic MSP environment surrounded by sun, sea, and cutting-edge technology, apply now and join our team in the Cayman Islands!

Desired Skills:

• Network administration
• Windows Server
• conditional access
• Intune
• Vmware
• HyperV
• Active Directory
• Micorsoft 365 Administration

Desired Work Experience:

• 5 to 10 years

Desired Qualification Level:

• Certificate

About The Employer:

Cayman Solution Providers (CSP) is a Cayman Islands-based managed I.T. services and cybersecurity firm specializing in secure, resilient, and compliant technology solutions for regulated businesses. With deep expertise across networks, Office 365 and Azure cloud environments, telecommunications, CIMA cybersecurity compliance, and 3CX hosted PBX systems, CSP delivers end-to-end support spanning infrastructure design, cybersecurity hardening, business continuity, and ongoing managed services. As a local on-island partner, CSP combines fast response times with enterprise-grade tooling-such as Fortinet and SentinelOne-to provide clients with dependable protection against modern threats while supporting their long-term operational and regulatory needs.

Employer & Job Benefits:

• basic medical
• car allowance
• phone allowance