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Loggerhead

Florida reciprocal homeowners insurer

IT Systems Administrator

System Administration +1Confirmed live in the last 24 hours
Full-timeTampa, FL, USANo salary listed

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 the Company

Loggerhead

Florida reciprocal homeowners insurer

Loggerhead is a Florida homeowners insurer that uses a reciprocal structure where policyholders are owners, managed by an Attorney in Fact to underwrite and administer property coverage. It offers Essential, Enhanced, and Elite homeowners plans with coverage for property, liability, belongings, and living expenses, plus add-ons like Loggerhead Shield, with an online portal and a network of independent agents to manage policies and claims. The company differentiates itself through its owner-focused reciprocal model, deep Florida P&C leadership, strong Demotech A rating, and its role as a major capacity provider after absorbing about 115,000 Progressive Home policies in late 2023/early 2024. Its goal is to deliver comprehensive, affordable Florida-specific coverage while leveraging technology and agent channels to streamline service and focus on catastrophe resilience.

Company size
51-200
Company stage
Not listed
Total funding
Not listed
Headquarters
Tampa, FL
Founded
2022

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