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

📍 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!