📍 Location: Grand Cayman, Cayman Islands
💼 Employment Type: Full-Time, On-Site
💰 Compensation: USD $60,000 – $80,000 (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.
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 Outsoured or Managed Service Provider (MSP) environment
✅ Strong technical knowledge of:
* Microsoft 365 (Intune, Exchange, Conditional Access)
* Windows Server 2016/2019/2022
* 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 $60,000 – $80,000 (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!