Senior Help Desk Administrator

Senior Help Desk Administrator

• Hybrid
• Seffner, FL Guardian Fleet Services is seeking a Senior Help Desk Administrator to provide advanced technical support, oversee day-to-day help desk operations, and serve as a mentor to support team members. This role is responsible for supporting employee equipment, business applications, user accounts, and IT service requests across multiple locations. The ideal candidate combines strong technical troubleshooting skills with a customer-focused approach and the ability to guide less experienced technicians. This is a hands-on position that plays a key role in ensuring employees can effectively utilize technology to support business operations.

Compensation

$60,000 - $75,000 annually, based on experience and qualifications Essential Responsibilities: End User Support & Device Management Provide technical support for Windows computers, mobile devices, printers, and related hardware. Troubleshoot and resolve hardware, operating system, and performance issues. Configure and deploy company-issued equipment.

Coordinate equipment setup, recovery, and logistics during employee onboarding, offboarding, and role changes. Maintain accurate hardware inventory and asset records. Coordinate repairs, replacements, and vendor support as needed. Application & Account Administration Support Microsoft 365 applications, including Outlook, Teams, OneDrive, and SharePoint.

Assist users with business-critical applications, including TOPS, Towbook, and Samsara. Provision, modify, and remove user access across approved systems. Troubleshoot authentication, password, multifactor authentication, and account access issues. Perform routine Microsoft 365 and Microsoft Entra ID administration. Network & Connectivity Support Troubleshoot wired and wireless connectivity issues impacting employees and locations.

Perform initial network diagnostics and identify service-impacting issues. Utilize Cisco Meraki tools to assist with connectivity troubleshooting. Escalate advanced network and infrastructure issues to appropriate technical teams. Help Desk Leadership & Service Delivery Serve as an escalation point for complex support requests.

Mentor and support help desk technicians through technical troubleshooting and issue resolution. Assist with ticket prioritization and workload coordination to ensure timely service. Maintain knowledge base articles, standard operating procedures, and support documentation. Identify recurring issues and recommend improvements to support processes and user experience.

Follow established security practices, approval workflows, and incident escalation procedures.

Qualifications

Required Minimum of three (3) years of progressive experience in Help Desk, Desktop Support, or IT Support roles. Strong troubleshooting skills involving Windows operating systems, Microsoft 365, mobile devices, and computer hardware. Experience administering Microsoft 365 and Microsoft Entra ID user accounts and permissions.

Experience supporting employee onboarding, offboarding, and access management processes. Working knowledge of networking fundamentals, including wired and wireless connectivity troubleshooting. Experience utilizing ticketing systems, remote support tools, and technical documentation. Strong communication, organizational, and customer service skills.

Ability to effectively mentor and support junior technicians. Ability to meet the initial on-site requirements for the hybrid work schedule. Preferred Experience supporting employees across multiple office or operational locations. Experience with TOPS, Towbook, Samsara, Kaseya, Datto, AutoTask, or IT Glue. Familiarity with Cisco Meraki and Microsoft Intune.

Experience in the towing, transportation, logistics, or fleet services industry. Previous experience serving as a senior escalation resource or team mentor. Microsoft, CompTIA, or other relevant IT certifications.

Benefits

Paid Time Off & Paid Holidays Medical, Dental, & Vision plans $15k Employer paid Life Insurance and AD&D Pet Insurance (NEW!) 401(k) plan Short Term & Long-Term Disability Hospital Indemnity Cancer Plan Accident Insurance Employee Assistance Program Employee Referral Bonus We are an Equal Opportunity Employer and are committed to building a diverse and inclusive workforce.

All qualified applicants will receive consideration for employment without regard to race, color, religion, sex (including pregnancy, sexual orientation, and gender identity), national origin, age, disability, genetic information, veteran status, or any other protected status under applicable federal, state, or local laws.

We believe that diversity strengthens our organization and are dedicated to providing a workplace free of discrimination, harassment, and retaliation. Employment decisions are based on qualifications, merits, and business needs.