Remote IT Systems Administrator – M365, HubSpot & Five9

Loggerhead Risk Management LLC; Tampa (FL); Hybrid; USD 65,000 - 95,000; Full time

Benefits offered by this job

401(k)

Dental insurance

Health insurance

STD/LTD

Life Insurance

Paid time off

Vision insurance

Referral Program

Tuition Reimbursement

Job summary

Loggerhead Risk Management LLC is seeking an IT Systems Administrator to support enterprise platforms and day-to-day IT services for a hybrid workforce. You will manage Microsoft 365, Intune, HubSpot CRM, and Five9, serving as a primary contact for IT requests.

The role suits an experienced IT professional who enjoys solving problems, owning outcomes, and improving systems in a remote-first, contact center environment.

Qualifications

• 3+ years of experience in IT support or system administration.
• 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.

Responsibilities

• 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, and connectivity issues.
• Troubleshoot connectivity, device compliance, authentication (MFA), and performance issues.
• Ensure users are properly configured for secure remote access across all enterprise systems.
• Troubleshoot hardware, software, access and system-related issues for both remote and in-office staff.
• Communicate clearly with users, ensuring transparency and follow-up.
• 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 patching and asset management across a distributed environment.
• Provide support for Five9 contact center operations, including login, routing, and availability issues.
• Execute onboarding, role changes, and offboarding processes across multiple systems.

Skills

IT support experience

Problem solving

Clear communication

Independent work

Remote collaboration

Tools

Microsoft 365

Intune

HubSpot CRM

Five9

Azure (optional)

Job description

Loggerhead Risk Management LLC is seeking an IT Systems Administrator to support enterprise platforms and day-to-day IT services for a hybrid workforce. You will manage Microsoft 365, Intune, HubSpot CRM, and Five9, serving as a primary contact for IT requests.

The role suits an experienced IT professional who enjoys solving problems, owning outcomes, and improving systems in a remote-first, contact center environment.