IT Specialist

We are a high-volume, multi-location automotive group seeking a dynamic and proactive IT Specialist to join our technology team. We pride ourselves on delivering exceptional customer experiences backed by a modern, reliable technology infrastructure. In this role, you will deliver exceptional technical support across various platforms, troubleshoot hardware and software issues, and ensure seamless network operations.

As our operations continue to grow, we are looking for a technically sharp IT Specialist who can take ownership of our systems, protect our network, and keep our teams operating without interruption. You will help optimize technology across multiple locations, support end users, strengthen system security, and contribute to a reliable and efficient technology environment. This position offers an opportunity to grow your skills in a fast-paced setting while making a direct impact on daily operations., * VoIP Phone Systems. Configure, maintain, and troubleshoot VoIP phone systems to support clear and uninterrupted communication across all departments and locations.

• Network Administration. Manage LAN/WAN infrastructure, including switches, routers, firewalls, wireless access points, and related equipment. Monitor network performance and quickly resolve connectivity or stability issues.
• Hardware & Device Support. Set up, image, configure, maintain, and troubleshoot desktops, laptops, servers, printers, mobile devices, and other peripherals. Organize and track IT equipment and maintain replacement and upgrade schedules.
• Microsoft 365 & Email Support. Manage user accounts, permissions, mailboxes, distribution lists, spam filtering, and email security across Microsoft 365, Outlook, and dealership-specific communication platforms.
• Cybersecurity. Maintain firewalls, antivirus software, endpoint protection, VPNs, multifactor authentication, access controls, and other security measures. Monitor for potential threats and respond promptly to security concerns.
• Technical Support. Diagnose and resolve hardware, software, network, and application issues for users across multiple locations. Provide clear and patient support to employees with varying levels of technical experience.
• System Maintenance & Improvements. Perform software updates, hardware refreshes, system upgrades, and infrastructure improvements with minimal disruption to daily operations. Collaborate with team members to identify performance issues and implement practical solutions.
• AI & Process Efficiency. Stay familiar with AI tools, automation platforms, and emerging technologies that can improve workflows, reduce repetitive tasks, and increase operational efficiency while protecting company and customer data.
• Documentation & Asset Management. Maintain accurate records of technical issues, solutions, system configurations, network diagrams, licenses, warranties, and IT inventory using Jira or a similar ticketing and documentation platform.

• Bachelor’s degree in Information Technology, Computer Science, or a related field preferred. Equivalent hands-on experience, technical training, or certifications will be considered.
• Three or more years of IT support or systems administration experience in a fast-paced business environment. Multi-location experience is preferred.
• Strong knowledge of Microsoft 365, including Outlook, Exchange Online, Teams, SharePoint, OneDrive, Entra ID and Intune.
• Solid understanding of networking technologies, including TCP/IP, DNS, DHCP, LAN/WAN, wireless networks, VPNs, firewalls, and VoIP systems.
• Strong troubleshooting skills across Windows 11, servers, computer hardware, printers, mobile devices, software, and peripherals. Familiarity with macOS and Linux is a plus.
• Working knowledge of cybersecurity practices, including multifactor authentication, endpoint protection, access controls, email security, patching, and incident response.
• Experience with ticketing, remote-support, documentation, and asset-management platforms such as Jira or similar systems.
• Familiarity with AI tools, automation platforms, cloud applications, and current workplace technology.
• Strong problem-solving, communication, and customer-service skills.
• Organized, dependable, and able to manage multiple priorities with minimal supervision.
• Proactive and accountable, with a strong sense of urgency and a commitment to following issues through to resolution.
• Able to travel between locations and work effectively with employees, leadership, vendors, and outside technology partners.

Pulled from the full job description

• Referral program
• Health insurance
• 401(k) matching
• Paid time off
• Employee discount
• Health savings account, * Competitive compensation and a comprehensive benefits package.
• A stable, growing organization with established dealership locations in the Chicago area.
• Hands-on experience with modern IT infrastructure, cloud-based systems, cybersecurity tools, AI, and emerging automotive technology.
• A fast-paced environment where your work has a direct impact on daily operations.
• A leadership team that values initiative, accountability, problem-solving, and continued professional growth.

Pay: $62,500.00 - $66,500.00 per year, * 401(k) matching

• Employee discount
• Health insurance
• Health savings account
• Paid time off
• Referral program