Senior Help Desk Administrator

Guardian Fleet Services; 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

Position:Senior Help Desk Administrator

Location: 730 Cactus Ridge Circle

Suite A

Seffner, FL

Job Id:1797-Guardian

# of Openings:1

Senior Help Desk Administrator - Hybrid - Seffner, FL

Note: This is not a remote position

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

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 Offered:

• Paid Time Off & Paid Holidays


• $15k Employer paid Life Insurance and AD&D


• Pet Insurance (NEW!)


• 401(k) plan


• Short Term & Long-Term Disability


• Hospital Indemnity


• Cancer Plan


• 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.