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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
Vacancy posted more than 2 months ago

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