IT Helpdesk Analyst

At TransChicago Truck Group, we keep the trucks and people that power our economy rolling. We’re a full-service commercial truck dealership representing Freightliner and Western Star by providing sales, service, and parts for the trucks that keep goods on the road. We’re a family-owned, fast-growing dealership group that values curiosity, teamwork, and growth. If you’re the kind of person who likes to learn by doing and see the impact of your work every day, you’ve found the right spot. We’re looking for an IT Helpdesk Analyst to support end users across TransChicago and serve as the primary escalation point for complex technical issues. In this role, you’ll deliver responsive, customer-focused support while troubleshooting and resolving hardware, software, network, and system issues. You’ll also help develop support processes and documentation and contribute to IT projects that improve operational efficiency and technology performance. This role is fully onsite at our Elmhurst dealership location. Essential Functions & Responsibilities: Serve as the primary escalation point for complex technical issues, providing in-person support at our Elmhurst dealership and remote support for other locations. Troubleshoot workstation, application, network, and connectivity problems. Diagnose and resolve Microsoft 365, Active Directory, Azure/Entra ID, VPN, and email issues. Perform root cause analysis on recurring incidents and implement permanent solutions. Support after-hours and emergency troubleshooting when required. Setup, provision, and recondition hardware and software for new and terminated employees, including laptops, desktops, docking stations, monitors printers etc. Provide first-level support remotely, assisting with hardware and software over the phone and remote desktop tools. Monitor ticket queues to ensure service level agreements (SLAs) are met. Prioritize incidents based on business impact and urgency. Manage escalations between Help Desk, Infrastructure, Security, and third-party vendors. Familiarity with a modern networking stack; DHCP, DNS, VPN, SSL Assist with managing some Fortigate firewall policies and troubleshooting connectivity between sites and thru firewalls. Maintain IP-based phone system, PBX, by adding/removing extensions and modifying call flows for business needs. Manage a Unifi network stack across multiple locations, set DHCP reservations, troubleshoot DNS and SSL issues. Provision users for VPN access. Education and/or required experience: Associate degree in Information Technology, Compute Science, Information Systems or related field preferred. Equivalent experience acceptable as well. Strong user-focused background and attitude 2+ years of IT support/helpdesk experience 1+ years supporting enterprise environments Experience troubleshooting endpoint hardware/software, Microsoft 365 applications, AD/Entra, printers, mobile phones. Microsoft 365/Azure certifications preferred Compensation & Benefits: Compensation: $50,000-$65,000. Salary will be determined based on experience, competencies, certifications and education. Benefits: Medical Insurance Vision Insurance Dental Insurance Life and AD&D Insurance Disability Insurance Flexible Spending Account (FSA) 401(k) with company match Paid Time Off (PTO) Paid Sick Time Paid Holidays Additional voluntary benefits: We also offer a variety of other benefits including an Employee Assistance Program (EAP), Accident Coverage, Critical Illness, Cancer Insurance, Pet Insurance, and Identity Theft Insurance TransChicago Truck Group is committed to a diverse and inclusive workplace. TransChicago is an equal opportunity employer and does not discriminate based on race, national origin, gender, gender identity, sexual orientation, protected veteran status, disability, age, or other legally protected status.