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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 TriageDeliver a high-quality, employee-focused support experience with strong responsiveness expectationsTriage, categorize, and prioritize tickets; resolve issues efficientlyEscalate requests to appropriate teams while maintaining ownership through resolution

Remote Workforce SupportProvide technical support for a primarily remote user base, including VPN, identity, endpoint, collaboration and connectivity issuesTroubleshoot connectivity, device compliance, authentication (MFA), and performance issuesEnsure users are properly configured for secure and efficient remote access across all enterprise systems

End-User SupportTroubleshoot hardware, software, access, and system-related issues across business platformsSupport both remote and in-office employees with consistent and professional experienceCommunicate clearly with users, ensuring transparency, follow-up, and issue resolution

System AdministrationAdminister and support Microsoft 365 (Exchange, Teams, SharePoint, Entra ID)Manage Microsoft Intune for device enrollment, compliance, and policy managementSupport HubSpot CRM administration (users, tickets, pipelines, workflows)Perform system configuration and user provisioning, permissions, and system configurationPerform advanced troubleshooting and remediation across supported platforms

Patch, Asset & Operational ManagementPerform system and endpoint patching to maintain security and stability across a distributed environmentMaintain accurate inventory of remote devices, hardware, and softwareSupport 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 configurationTroubleshoot issues impacting call availability, routing, agent state, and performanceCoordinate with internal teams and vendors when contact center issues impact business operationsPrioritize and respond to contact center-related issues with urgency due to direct business impact

User Lifecycle ManagementExecute onboarding, role changes, and offboarding processesProvision and manage user accounts across Microsoft 365, HubSpot, and Five9Ensure new hires, especially remote and contact center users, are fully enabled on Day 1Enforce access controls aligned with security and compliance standards

Problem Solving & Solution OwnershipDiagnose recurring or complex issues and implement lasting fixesDevelop practical solutions to technical and operational challengesOwn issues from intake through resolution with clear follow-upIdentify and improve recurring remote user or contact center issues

SME Development & Continuous ImprovementBuild deep expertise in enterprise systems over time (M365, Intune, HubSpot, and Five9)Identify opportunities for process improvement, automation, and operational efficiencySupport workflow enhancements, integrations, and reporting initiativesContribute to improving IT service delivery and remote support maturity

Documentation & Knowledge ManagementCreate and maintain SOPs, knowledge base articles, and troubleshooting guidesDocument common remote support scenarios and contact center workflowsShare knowledge across the IT team to strengthen support capabilities

Qualifications

Required

3+ years of experience in IT support or system administrationHands-on experience with Microsoft 365 tenant administrationExperience with endpoint/device management (Intune or similar MDM)Experience with Help Desk or ticketing systemsExperience supporting a remote workforceDemonstrated ability to troubleshoot complex issues and drive resolutionStrong verbal and written communication skills, including the ability to clearly explain issues and present solutionsSelf-motivated with the ability to work independently and manage competing prioritiesWillingness to support evenings and weekends as business needs require

Preferred

Experience with HubSpot CRM or similar platformsExposure 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 automationRelevant certifications (Microsoft, CompTIA, or equivalent)Working ConditionsMust reside in the Tampa Bay marketHybrid role requiring at least 2 onsite days per week, with additional onsite support as needed for hardware, onboarding/offboarding, or incident responseSupports a remote-first workforce and live contact center operationsOccasional evening or weekend support may be requiredWorks 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.

Job Type: Full-time

Benefits:

401(k)Dental insuranceHealth insuranceSTD/LTDLife InsurancePaid time offVision insuranceReferral ProgramTuition Reimbursement

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