IT System Administration
Loggerhead Insurance
IT Systems Administrator
As an IT Systems Administrator, you will support the enterprise platforms and day-to-day IT services that keep our hybrid workforce connected and productive. You will help manage Microsoft 365, Intune, HubSpot CRM, and Five9 Contact Center while serving as a key first point of contact for incoming IT requests. This role is a great fit for an experienced IT professional who enjoys solving problems, communicating clearly, taking ownership, and improving systems and support processes in a remote-first, contact center-focused environment where responsiveness and reliability matter.
Key Responsibilities
- Service Desk & Ticket Triage
- Remote Workforce Support
- End-User Support
- System Administration
- Patch, Asset & Operational Management
- Contact Center System Support (Five9)
- User Lifecycle Management
- Problem Solving & Solution Ownership
- SME Development & Continuous Improvement
- Documentation & Knowledge Management
Qualifications
Required
- 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
- Demonstrated ability to troubleshoot complex issues and drive resolution
- Strong verbal and written communication skills, including the ability to clearly explain issues and present solutions
- Self-motivated with the ability to work independently and manage competing priorities
- Willingness to support evenings and weekends as business needs require
Preferred
- Experience with HubSpot CRM or similar platforms
- Exposure to contact center solutions (Five9 or equivalent)
- Familiarity with identity and access management concepts (MFA, SSO, RBAC)
- Interest or experience in cloud technologies (Azure), DevOps, or automation
- Relevant certifications (Microsoft, CompTIA, or equivalent)
Working Conditions
- Must reside in the Tampa Bay market
- Hybrid role requiring at least 2 onsite days per week, with additional onsite support as needed for hardware, onboarding/offboarding, or incident response
- Supports a remote-first workforce and live contact center operations
- Occasional evening or weekend support may be required
- Works in a fast-paced environment with competing priorities and urgent escalations
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