IT Systems Administrator — Remote-First Enterprise Support

Loggerhead Insurance; Tampa (FL); Hybrid; USD 70,000 - 95,000; Full time

Job summary

Loggerhead Insurance is seeking an IT Systems Administrator to support enterprise platforms and day-to-day IT services for a hybrid, remote-first workforce. You will manage Microsoft 365, Intune, HubSpot CRM, and Five9, acting as a first point of contact for IT requests.

The role emphasizes problem solving, clear communication, ownership, and process improvement in a fast-paced environment. The position focuses on delivering reliable end-user support for both remote and in-office staff, with

Qualifications

• 3+ years of 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.
• Strong verbal and written communication skills.
• Willingness to support evenings and weekends as business needs require.

Responsibilities

• Deliver high-quality, employee-focused support 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 remote user base, including VPN, identity, endpoint, collaboration and connectivity issues.
• Troubleshoot connectivity, device compliance, authentication (MFA), and performance issues.
• Administer and support Microsoft 365 (Exchange, Teams, SharePoint, Entra ID) and Intune.

Skills

IT support

Remote work

Communication skills

Independent work

Evening/weekend availability

Tools

Microsoft 365

Intune

HubSpot CRM

Five9

VPN

MFA

Entra ID

Job description

Loggerhead Insurance is seeking an IT Systems Administrator to support enterprise platforms and day-to-day IT services for a hybrid, remote-first workforce. You will manage Microsoft 365, Intune, HubSpot CRM, and Five9, acting as a first point of contact for IT requests.

The role emphasizes problem solving, clear communication, ownership, and process improvement in a fast-paced environment. The position focuses on delivering reliable end-user support for both remote and in-office staff, with