System Administrator

Windward Risk Managers • Boca Raton, FL

10d • Onsite

About The Position

We are seeking a motivated System Administrator to join our IT team. This role combines hands-on systems administration with technical mentorship responsibilities, offering an excellent opportunity for professional growth. The ideal candidate will maintain and improve our technology infrastructure while helping develop the technical capabilities of our support staff.

Requirements

• 3-5 years of experience in IT support, desktop support, or junior systems administration
• Working knowledge of Windows Server environments, Active Directory, and Office 365 administration
• Understanding of networking fundamentals (TCP/IP, DNS, DHCP, VLANs) and basic network troubleshooting
• Experience with virtualization technologies (VMware preferred) and cloud services (Azure preferred)
• Basic scripting abilities in PowerShell with demonstrated interest in automation
• Strong problem-solving skills with ability to work independently and prioritize multiple tasks
• Excellent communication skills with proven ability to explain technical concepts to non-technical users
• Candidates must be authorized to work for any employer in the U.S. without requiring visa sponsorship now or in the future.

Nice To Haves

• Associate degree in Information Technology or related field (or equivalent experience/certifications)
• Industry certifications such as CompTIA A+, Network+, or Microsoft certifications
• Experience with backup solutions, monitoring tools, and ticketing systems
• Familiarity with ITIL framework and best practices
• Knowledge of security principles and compliance requirements

Responsibilities

• Install, configure, and maintain Windows/Linux servers, VMware virtual environments, and Azure cloud resources while ensuring optimal performance and security
• Administer Active Directory infrastructure including user accounts, security groups, Group Policy, and organizational units; manage Office 365 ecosystem including Exchange Online, OneDrive, Teams, and Intune
• Develop PowerShell scripts and automation tools to streamline IT operations, reduce manual tasks, and improve service delivery across departments
• Monitor system performance, troubleshoot complex issues, and implement preventive maintenance procedures to minimize downtime and ensure business continuity
• Serve as technical escalation point and mentor for Help Desk team, providing guidance on troubleshooting methodologies and conducting regular knowledge transfer sessions
• Create and maintain comprehensive documentation including system configurations, standard operating procedures, runbooks, and knowledge base articles
• Coordinate with vendors for technical support and oversee software licensing management.
• Support backup and disaster recovery operations, perform regular system updates and patches, and participate in on-call rotation as needed

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: Associate degree