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Agent guide: [/agents.md](https://www.wearedevelopers.com/agents.md). --- # IT System Administration - **Company:** LOGGERHEAD BUSINESS & INSURANCE MANAGEMENT, LLC - **Location:** Tampa, FL, United States (Remote available) - **Experience:** Experienced - **Contract:** Permanent contract - **Skills:** Microsoft Access, Microsoft Windows, Microsoft Azure, Cloud Computing, System Configuration, DevOps, Distributed Computing Environment, Identity and Access Management, Issue Tracking Systems, Virtual Private Networks (VPN), Knowledge Management, Role-Based Access Control, Remote Access Technology, Microsoft SharePoint, User Provisioning Software, Office365, Microsoft InTune, Information Technology, Hubspot, User Accounts - **Published:** June 29, 2026 - **Apply:** https://www.indeed.com/viewjob?jk=627fba7e87559d6b ## About the Role Do you have experience in Ticketing system technical support?, * 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) ## Description 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., 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 ## Related Videos - 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