Hybrid Senior Help Desk Lead - IT Support & Mentorship

Guardian Fleet Services Inc.; Seffner (FL); Hybrid; USD 60,000 - 75,000; Full time

Benefits offered by this job

Paid Time Off

Paid Holidays

Life Insurance

401(k) plan

Short/Long-Term Disability

Hospital Indemnity

Employee Assistance Program

Job summary

Guardian Fleet Services Inc. is seeking a Senior Help Desk Administrator in Seffner, FL for a hybrid role. You will lead day-to-day help desk operations, support Windows devices, Microsoft 365 apps, and user accounts, and mentor junior technicians across locations to ensure smooth IT service delivery.

You will also manage onboarding/offboarding processes, asset inventory, and vendor escalations while maintaining high customer service standards and security practices.

Qualifications

• Minimum of three (3) years of progressive experience in Help Desk, Desktop Support, or IT Support roles.
• Strong troubleshooting skills involving Windows OS, 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.

Responsibilities

• Provide advanced technical support for Windows computers, mobile devices, printers, and related hardware.
• Troubleshoot and resolve hardware, OS, and performance issues.
• Configure and deploy company-issued equipment.
• Coordinate equipment setup, recovery, and logistics during onboarding and offboarding.
• Maintain accurate hardware inventory and asset records.
• Coordinate repairs, replacements, and vendor support as needed.
• Support Microsoft 365 apps including Outlook, Teams, OneDrive, SharePoint.
• Assist users with business-critical applications like TOPS, Towbook, Samsara.
• Provision and manage user access across systems.
• Troubleshoot authentication and MFA issues; manage Entra ID accounts.
• Perform routine Microsoft 365 administration.
• Troubleshoot wired/wireless connectivity; use Cisco Meraki tools.
• Escalate complex network issues to appropriate teams.
• Mentor help desk technicians and manage ticket prioritization.
• Maintain knowledge bases and SOPs; suggest process improvements.

Skills

Windows troubleshooting

Microsoft 365

Entra ID administration

Onboarding/offboarding

Networking fundamentals

Ticketing systems

Mentoring/leadership

Customer service

Tools

TOPS

Towbook

Samsara

Kaseya

Datto

AutoTask

IT Glue

Cisco Meraki

Job description

Guardian Fleet Services Inc. is seeking a Senior Help Desk Administrator in Seffner, FL for a hybrid role. You will lead day-to-day help desk operations, support Windows devices, Microsoft 365 apps, and user accounts, and mentor junior technicians across locations to ensure smooth IT service delivery.

You will also manage onboarding/offboarding processes, asset inventory, and vendor escalations while maintaining high customer service standards and security practices.