HybridHybrid; at least 2 onsite days per week, with additional onsite support as needed.
IT OperationsIT Service Desk & End User Support
About the job
Requirements
At least 3 years of experience in IT support or system administration.
Hands-on experience with Microsoft 365 tenant administration.
Experience with endpoint or device management using Intune or a similar mobile device management platform.
Experience with help desk or ticketing systems.
Experience supporting a remote workforce.
Ability to troubleshoot complex issues and drive them to resolution.
Strong verbal and written communication skills, including the ability to clearly explain issues and present solutions.
Ability to work independently, stay self-motivated, and manage competing priorities.
Willingness to support evenings and weekends as business needs require.
Must reside in the Tampa Bay market.
Must be able to work onsite at least 2 days per week, with additional onsite support as needed for hardware, onboarding or offboarding, or incident response.
Responsibilities
Deliver a responsive, employee-focused support experience.
Triage, categorize, and prioritize tickets, resolving issues efficiently.
Escalate requests to appropriate teams while maintaining ownership through resolution.
Provide technical support for a primarily remote user base, including VPN, identity, endpoint, collaboration, and connectivity issues.
Troubleshoot connectivity, device compliance, authentication including multi-factor authentication, and performance issues.
Ensure users are configured for secure and efficient remote access across enterprise systems.
Troubleshoot hardware, software, access, and system-related issues across business platforms.
Support remote and in-office employees with a consistent and professional experience.
Communicate with users about issue status, follow up, and ensure resolution.
Administer and support Microsoft 365, including Exchange, Teams, SharePoint, and Entra ID.
Manage Microsoft Intune for device enrollment, compliance, and policy management.
Support HubSpot CRM administration, including users, tickets, pipelines, and workflows.
Perform system configuration, user provisioning, and permissions management.
Perform advanced troubleshooting and remediation across supported platforms.
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.
Support contact center agents and operations, including login and access issues, call-handling disruptions, and system configuration.
Troubleshoot issues affecting call availability, routing, agent state, and performance.
Coordinate with internal teams and vendors when contact center issues affect business operations.
Prioritize and respond urgently to contact center issues because of their direct business impact.
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 enabled on their first day.
Enforce access controls aligned with security and compliance standards.
Diagnose recurring or complex issues and implement lasting fixes.
Develop practical solutions to technical and operational challenges.
Own issues from intake through resolution and provide clear follow-up.
Identify and improve recurring remote-user or contact-center issues.
Build deep expertise in Microsoft 365, 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.
Create and maintain standard operating procedures, 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.
Desired Qualifications
Experience with HubSpot CRM or similar platforms.
Exposure to contact center solutions such as Five9 or equivalent.
Familiarity with identity and access management concepts, including multi-factor authentication, single sign-on, and role-based access control.
Interest or experience in cloud technologies such as Azure, DevOps, or automation.
Relevant Microsoft, CompTIA, or equivalent certifications.
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.