DriveTime Automotive Group, Inc.

Traveling Systems Administrator (Chicago & Surrounding Areas)

Career Site Title
Traveling Systems Administrator
Job ID
Information Technology
Regular Full-Time
Business Unit
14500 S Cicero Ave


What Drives You?

  • Career paths with opportunities to learn vital roles and skills?
  • Meaningful work in a stable, promote-from-within organization?
  • Professional satisfaction and helping others
  • A workspace that is dynamic, fast, fun, and challenging? 

DriveTime is more than a company. We’re a true team of strong, highly motivated performers that is committed to ensuring the success of each customer—and of each professional. If you have a real passion for continual learning and growth, are flexible enough to handle various roles, and feel compelled to do what you know is right, we may have an excellent opportunity for you.


As a Systems Administrator (SA) you’ll work in the IT Field Support Group that is responsible for supporting the IT hardware and software used by 150+ retail facilities located throughout the U.S. You’ll do everything from fixing a failed WiFi device to working with a team member and several vendors to install all of the technology in a new facility. You will be required to work from our facility in Chicago, IL and (frequently) drive or fly to remote locations. This position requires a significant amount of travel on a regular basis (averages 50% or more during busy periods)..

  • Work with other team members located throughout the U.S. to build new retail facilities (dealerships, vehicle inspection centers, service centers, etc.)
  • Work with our Corporate Help Desk to help troubleshoot problems related to the voice & data networks, servers, applications and hardware devices that support your retail facilities.
  • Monitor and work on tickets that you’re assigned, follow-up with your customers, and try to resolve issues within our Service Level Agreement (SLA). You will be expected to manage Help Desk ticket escalations during normal and after business hours. This includes providing customer and vendor support especially during localized or system wide outages. In emergency situations you may be required to travel to the location experiencing an outage with little-to-no notice.
  • Perform extensive research on products and services for projects that you’re assigned.
  • Provide project updates and weekly status reports to your manager.


Just a few of the Benefits:

  • Work with latest tools and technologies
  • Medical, Dental, Wellness & Vision Plans
  • Technical training and continued education opportunities
  • A culture of opportunity and promotion from within
  • Competitive Pay
  • 401K Plan with company contribution
  • Company supplied vehicle (*)
  • Company supplied cell phone (*)
  • Company supplied credit card for travel expenses (*)

Technical Advancement:

Our engineers are given everything they need to be successful with emerging technologies, including access to live online classroom training, recorded training sessions and boot-camp classes offered by IT Certified Training centers. 


*Must adhere to company guidelines and restrictions



  • A Bachelor’s Degree or higher in a related field, or professional experience working with related technologies
  • Minimum 3-5 years of experience in a systems administrator role in a corporate Windows environment
  • Minimum 3-5 years of experience with basic router and switch troubleshooting in a corporate environment
  • Strong network and hardware troubleshooting skills
  • Excellent written, communication, collaboration and interpersonal skills 

And when it comes to hiring, we don't just look for the right person for the job, we seek out the right person for DriveTime. Along the way, we provide plenty of opportunity to be creative and grow professionally in a fun, high-energy environment. DriveTime is a drug-free, tobacco-free workplace, and an Equal Opportunity Employer.





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