IT System Administration

About Loggerhead Risk Management LLC Loggerhead is a property and casualty insurer that specializes in providing coverage that meets the unique needs of Florida homeowners. We’re a team of insurance professionals with customer service as our core value, and we understand the importance of providing attentive service to our policyholders. Loggerhead is powered by modern technology, guided by people who share a commitment to trust, empathy, always doing what’s right, flexibility, and teamwork. Role Overview 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 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 Remote Workforce Support 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 End-User Support 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 System Administration Administer and support Microsoft 365 (Exchange, Teams, SharePoint, Entra ID) Manage Microsoft Intune for device enrollment, compliance, and policy management Support HubSpot CRM administration (users, tickets, pipelines, workflows) Perform system configuration and user provisioning, permissions, and system configuration Perform advanced troubleshooting and remediation across supported platforms Patch, Asset & Operational Management Perform system and endpoint patching to maintain security and stability across a distributed environment Maintain accurate inventory of remote devices, hardware, and software Support audits and lifecycle tracking of IT assets Contact Center System Support (Five9) Provide support for contact center agents and operations, including login/access issues, call-handling disruptions, and system configuration Troubleshoot issues impacting call availability, routing, agent state, and performance Coordinate with internal teams and vendors when contact center issues impact business operations Prioritize and respond to contact center-related issues with urgency due to direct business impact User Lifecycle Management Execute onboarding, role changes, and offboarding processes Provision and manage user accounts across Microsoft 365, HubSpot, and Five9 Ensure new hires, especially remote and contact center users, are fully enabled on Day 1 Enforce access controls aligned with security and compliance standards Problem Solving & Solution Ownership Diagnose recurring or complex issues and implement lasting fixes Develop practical solutions to technical and operational challenges Own issues from intake through resolution with clear follow-up Identify and improve recurring remote user or contact center issues SME Development & Continuous Improvement Build deep expertise in enterprise systems over time (M365, Intune, HubSpot, and Five9) Identify opportunities for process improvement, automation, and operational efficiency Support workflow enhancements, integrations, and reporting initiatives Contribute to improving IT service delivery and remote support maturity Documentation & Knowledge Management Create and maintain SOPs, knowledge base articles, and troubleshooting guides Document common remote support scenarios and contact center workflows Share knowledge across the IT team to strengthen support capabilities 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 ADA: The above statements cover what are generally believed to be the principal and essential functions of this job. Specific circumstances may allow or require some people assigned to the job to perform a somewhat different combination of job duties. Job Type: Full-time Benefits: 401(k) Dental insurance Health insurance STD/LTD Life Insurance Paid time off Vision insurance Referral Program Tuition Reimbursement