IT System Administration

About the Company

Loggerhead Risk Management LLC is a property and casualty insurer specializing in coverage that meets the unique needs of Florida homeowners. We are a team of insurance professionals with customer service as our core value, committed to providing attentive service to our policyholders. Loggerhead is powered by modern technology and guided by a shared commitment to trust, empathy, flexibility, and teamwork.

About the Role

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 ideal for an experienced IT professional who enjoys problem-solving, clear communication, taking ownership, and improving systems and support processes in a remote-first, contact-center-focused environment where responsiveness and reliability matter.

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 a 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, user provisioning, permissions, and advanced troubleshooting 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

Requirements

• 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 Qualifications

• 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

Benefits

• 401(k)
• Dental insurance
• Health insurance
• Short-Term Disability (STD) / Long-Term Disability (LTD)
• Life Insurance
• Paid time off
• Vision insurance
• Referral Program
• Tuition Reimbursement