Remote IT Systems Administrator: M365, Intune & Five9

Loggerhead Insurance; Tampa (FL); Hybrid; USD 65,000 - 95,000; Full time

Job summary

Loggerhead Insurance in the Tampa area is seeking an IT Systems Administrator to support enterprise platforms and day-to-day IT services for a hybrid workforce.

You will manage Microsoft 365, Intune, HubSpot CRM, and Five9, serving as the first point of contact for IT requests and helping improve system and support processes in a remote-first, contact center-focused environment where responsiveness and reliability matter.

Qualifications

• 3+ years of experience in IT support or system administration.
• Hands-on experience with Microsoft 365 tenant administration.
• Experience with endpoint/device management (Intune or similar MDM).
• Experience with Help Desk or ticketing systems.
• Experience supporting a remote workforce.

Responsibilities

• Deliver a high-quality, employee-focused support experience with strong responsiveness expectations.
• Triage, categorize, and prioritize tickets; resolve issues efficiently.
• Escalate requests to appropriate teams while maintaining ownership through resolution.
• Provide technical support for a primarily remote user base, including VPN, identity, endpoint, collaboration and connectivity issues.
• Troubleshoot connectivity, device compliance, authentication (MFA), and performance issues.
• Ensure users are properly configured for secure and efficient remote access across all enterprise systems.
• Troubleshoot hardware, software, access, and system-related issues across business platforms.
• Support both remote and in-office employees with consistent and professional experience.
• Communicate clearly with users, ensuring transparency, follow-up, and issue resolution.
• Administer and support Microsoft 365 (Exchange, Teams, SharePoint, Entra ID)
• Manage Microsoft Intune for device enrollment, compliance, and policy management
• Perform system configuration and user provisioning, permissions, and system configuration
• Perform advanced troubleshooting and remediation across supported platforms

Skills

IT support

System administration

Microsoft 365

Intune management

Help Desk software

Remote support

Troubleshooting

Communication skills

Time management

Independence

Tools

Microsoft 365

Intune

HubSpot CRM

Five9

Job description

Loggerhead Insurance in the Tampa area is seeking an IT Systems Administrator to support enterprise platforms and day-to-day IT services for a hybrid workforce.

You will manage Microsoft 365, Intune, HubSpot CRM, and Five9, serving as the first point of contact for IT requests and helping improve system and support processes in a remote-first, contact center-focused environment where responsiveness and reliability matter.