IT Field Technician

Position Summary

The IT Field Technician provides Tier 1 and Tier 1.5 technical support to employees across multiple dealership locations. This position serves as a primary point of contact for day-to-day technology issues while also handling more advanced troubleshooting that goes beyond traditional Tier 1 help desk support.

The ideal candidate is comfortable working independently, troubleshooting issues from initial report through resolution, supporting users both remotely and on-site, and determining when an issue requires escalation to higher-level IT resources.

Essential Responsibilities

• Provide Tier 1 and Tier 1.5 technical support to end users across multiple dealership locations.
• Troubleshoot Windows workstations, laptops, applications, printers, scanners, and other peripheral devices.
• Diagnose hardware, software, network, authentication, and connectivity issues.
• Provide remote and on-site technical support depending on the needs of the dealership.
• Troubleshoot issues beyond basic help desk procedures before escalating to higher-level IT staff or vendors.
• Configure, deploy, replace, and maintain Windows computers and related equipment.
• Support user accounts, passwords, permissions, and access through Active Directory, Microsoft 365, and other vendor applications.
• Troubleshoot wired and wireless network connectivity, including identifying whether problems originate from the endpoint, local network, ISP, or another infrastructure component.
• Support dealership-specific applications and equipment, including CDK and check/document scanning systems.
• Troubleshoot and setup hardware including printers, multifunction devices, scanners, monitors, docking stations, and other dealership hardware.
• Use remote-management tools to diagnose and resolve issues without requiring an on-site visit when possible.
• Assist with employee onboarding, offboarding, workstation moves, and equipment changes.
• Maintain accurate documentation of troubleshooting steps, configurations, equipment, and resolutions.
• Work with vendors and higher-level IT resources when an issue requires escalation while remaining involved through resolution.
• Participate in technology projects, hardware refreshes, software migrations, and other IT initiatives.
• Travel between dealership locations as needed to provide hands-on technical support.

Tier 1.5 Expectations

This position is expected to go beyond basic troubleshooting and scripted help desk procedures. The technician should be able to investigate unfamiliar problems, identify likely causes, test potential solutions, and resolve moderately complex issues independently.

Examples may include:

• Troubleshooting RemoteApp, virtual machine, or remote-access issues.
• Identifying whether a problem is related to the user's computer, account, network, server, or third-party service.
• Troubleshooting dealership hardware or software that requires coordination between multiple vendors.
• Reviewing logs, system settings, administrative consoles, and other diagnostic information to determine the cause of an issue.
• Recognizing infrastructure-level problems and gathering the necessary information before escalating them.

The technician is not expected to function as a systems or network administrator but should have enough technical knowledge to recognize and troubleshoot issues that extend beyond traditional Tier 1 support.

This position answers directly to the Director of IT of the Russ Darrow Group.

Must be able to travel to our corporate headquarters in Menomonee Falls and all 15 of our locations in the Metro Milwaukee area, West Bend, Madison, and Neenah. Mileage reimbursement is available.

Work Type: In-Person, non-remote

Qualifications

• Valid driver's license and ability to travel between dealership locations as required.
• Strong attention to detail with proven troubleshooting and problem-solving skills
• Effective verbal and written communication skills, with the ability to train and support users on new systems and software
• Ability to work independently with minimal supervision, while also collaborating effectively in a team environment
• Working knowledge of Active Directory.
• Familiarity with Microsoft 365 administration and troubleshooting.
• Understanding of basic TCP/IP networking, DNS, DHCP, Wi-Fi, and VPN concepts.
• Experience troubleshooting and installing computer hardware and peripheral devices.
• Ability to troubleshoot problems methodically rather than relying solely on documented fixes.
• Ability to communicate technical information clearly to non-technical users.
• Ability to prioritize multiple support requests in a multi-location environment.
• Ability to successfully pass a background check and drug screening

Preferred Qualifications

• Associate degree or technical training in Information Technology, Cybersecurity, Networking, or a related field.
• Previous experience in a Tier 1, Tier 1.5, Tier 2, desktop support, field technician, or similar technical support position.
• Experience supporting multiple physical locations.
• Experience with Microsoft 365, Exchange Online, Active Directory, Group Policy, and Windows administration.
• Experience with Meraki networking equipment.
• Experience with ConnectWise or similar remote monitoring and management tools.
• Experience supporting dealership management systems such as CDK is beneficial but not required.

Skills and Characteristics

Successful technicians in this position are curious and persistent troubleshooters. They should be comfortable receiving a problem they have not encountered before, researching and investigating the issue, and working toward a solution rather than immediately escalating it.

The position requires someone who can balance technical troubleshooting with customer service while supporting employees who rely on technology to keep dealership operations running.

About Us

The Darrow Difference is the foundation of our success - and we want you to be a part of it!

Are you outgoing, enjoy meeting new people, and have a passion for the latest technology? Are you looking for a fulfilling career and not just another job? At the Russ Darrow Group, we share the same commitment to our employees as we do our customers - after all, a great customer experience is only possible with great employees.


What We Offer

We believe in investing in our employees' growth and well-being, that's why we provide continuous training, advancement opportunities, competitive compensation, flexible schedules, comprehensive benefits, and employee assistance programs. Our culture emphasizes family values, diversity, and teamwork, ensuring exceptional service through empowered and dedicated team members.


No experience? No problem! We're eager to train the right candidates from the ground up. Our top-notch tools and resources will help you succeed! With over six decades of success, our experienced management teams will provide comprehensive training and support from day one.


If you're ready to join a team that values community involvement, career development, and a legacy of excellence, we'd love to hear from you!!

Benefits

• Competitive Compensation Plans
• Full Benefits Package
• Medical, Dental & Vision
• 401k with Company Match
• HSA with Company Contribution
• PTO from day one!!
• Growth and Advancement Opportunities