IT Support Specialist / Helpdesk Technician

Why Work for Trailer Equipment / Trailer X-Press?

At Trailer Equipment and Trailer X-Press, you’re not just joining a company—you’re joining a stable, growing organization with deep roots in Michigan’s transportation and logistics industry. We take pride in providing a supportive, people-focused workplace where employees can build meaningful careers, contribute to a high-performing team, and see the impact of their work every day.

Location: On-site in Byron Center, MI
Type: Full-Time
Travel: Some travel required
Schedule: Occasional weekend & after-hours coverage

We are seeking a motivated, service-oriented IT Support Specialist to serve as the primary frontline technician for a mid-sized transportation and logistics organization.

This highly visible role is ideal for someone who enjoys working directly with users, thrives in a fast-paced environment, and wants to grow into broader systems, infrastructure, and security responsibilities over time. You will be the go-to resource for daily technical support, device management, and user onboarding.

Key Responsibilities

Service Desk & End-User Support

• Serve as the first point of contact for Tier 1 and basic Tier 2 support requests
• Support issues, including: 
  • Password resets, account lockouts, and access issues
  • VPN and remote connectivity troubleshooting
  • Printer, scanner, and peripheral support
  • Windows laptop performance and OS troubleshooting
  • Mobile device setup and application support
  • Software installation and workstation configuration
• Triage, prioritize, resolve, and escalate tickets appropriately
• Deliver clear, consistent, and professional communication to end users

Onboarding & Offboarding Ownership

Onboarding

• Provision new user accounts, Microsoft 365 access, MFA, and licenses
• Prepare and deploy laptops, mobile phones, and required applications

Offboarding

• Perform secure account deactivation and access removal
• Recover and document all company assets

Asset Management & Device Lifecycle

• Maintain an accurate inventory of hardware and IT assets
• Deploy, redeploy, repair, and retire equipment
• Reimage and refurbish devices for future use
• Prepare and configure new devices for rollout
• Enforce accountability for assigned technology

Proactive IT Presence & Operational Support

• Conduct regular walkthroughs to identify issues before they become outages
• Support conference rooms, shared workstations, and common-area technology
• Maintain a friendly, visible, and approachable IT presence
• Identify recurring issues and recommend long-term solutions

Documentation & Continuous Improvement

• Create and maintain internal documentation and troubleshooting guides
• Help build standardized, repeatable processes to reduce downtime
• Track patterns in recurring incidents and support prevention efforts

Metrics & Reporting

Monitor and report on helpdesk performance, including:

• Ticket volume and trends
• Response and resolution times
• Recurring root-cause categories
• Weekly service improvement recommendations

Key Traits for Success

• Strong interpersonal and customer-focused communication skills
• Ownership mindset with accountability for follow-through
• Proactive, organized, and self-directed work style
• Ability to manage and prioritize tasks independently
• Interest in developing skills in systems administration, infrastructure, and security

Growth Opportunity

This role offers room to grow into:

• Systems administration
• Network & infrastructure support
• Cybersecurity operations
• IT project work

As the organization continues to expand, so will your opportunities to take on broader responsibilities and advanced technical challenges.

#ID26

Required Qualifications

• 1+ years of experience in Helpdesk, Desktop Support, or MSP environments
• Strong troubleshooting skills in Windows-based environments
• Experience supporting Microsoft 365, including: 
  • Exchange Online
  • Teams
  • OneDrive / SharePoint
  • User management & licensing
• Familiarity with WatchGuard products (VPN, Firebox, policies)
• Working knowledge of Windows Server technologies: 
  • Active Directory
  • Group Policy
  • Basic server administration

Preferred Skills

• Experience supporting multi-site or logistics/transportation environments
• Familiarity with imaging & deployment tools (MDT, Intune, Autopilot, SCCM)
• Basic networking knowledge (DNS, DHCP, VLANs)
• Experience coordinating with vendors and handling warranty cases
• Exposure to Power BI and CRM/ERP system support