IT System Administration

About this position

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, Hub Spot 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.

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

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

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

Administer and support Microsoft 365 (Exchange, Teams, SharePoint, Entra )Manage Microsoft Intune for device enrollment, compliance, and policy management

Support Hub Spot CRM administration (users, tickets, pipelines, workflows)
Perform system configuration and user provisioning, permissions, and system configuration

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

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

Execute onboarding, role changes, and offboarding processes

Provision and manage user accounts across Microsoft 365, Hub Spot, 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

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

Build deep expertise in enterprise systems over time (M365, Intune, Hub Spot, 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