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Technical Support Administrator

Remote / Online - Candidates ideally in
Downers Grove, DuPage County, Illinois, 60516, USA
Listing for: Cooper's Hawk Winery
Full Time, Remote/Work from Home position
Listed on 2026-01-07
Job specializations:
  • IT/Tech
    IT Support, HelpDesk/Support, Technical Support, Systems Administrator
Salary/Wage Range or Industry Benchmark: 55000 - 66000 USD Yearly USD 55000.00 66000.00 YEAR
Job Description & How to Apply Below

Cooper’s Hawk Winery & Restaurants is seeking an experienced Helpdesk/Technical Support Administrator to provide first class technical support to our restaurants and Restaurant Support Center team members.

The hours for this position are on a flexible rotating schedule. This role is part of the Information Technology team, which is based out of the Restaurant Support Center in Downers Grove, IL. We are open to hiring this as a hybrid position based out of our Downers Grove IL office, or as a remote position in the Phoenix, AZ area.

The Technical Support Administrator is responsible for ensuring the logging and timely resolution of IT service requests, incidents and problems by providing Level 1 and Level 2 Helpdesk Support to Cooper’s Hawk restaurant and corporate office team members. Main tasks include troubleshooting and restoring services to hardware and software systems, PCs, printers, mobile devices, Point‑of‑Sale equipment, A/V equipment, and other various IT and Business systems located in Cooper’s Hawk Environment.

This position requires someone that is customer‑service oriented and has strong troubleshooting skills.

What You’ll Do:
  • Problem & Incident Management:
    Log, respond to, and ensure timely closure of incoming problems and incidents to multi‑state restaurants and Restaurant Support Center by email, phone, chat or via Fresh service.
  • Troubleshooting:
    Diagnose and resolve PC, POS, technology infrastructure and Business application incidents, ensuring issues are addressed in a timely manner. Issues include, but not limited to, configuration, installation, and ongoing maintenance of workstations, business 3rd party and in‑house applications, point of sale, network equipment, operating systems, printers, internet connections, telephones, and mobile devices.
  • Escalation Management:
    Escalate complex issues to support supervisor, application support teams or 3rd party resolver groups as appropriate.
  • Hardware / Software management:
    Assist with the installation, configuration, and maintenance of hardware and software. Process requests for hardware and software in line with department policies. Image new or re‑purposed workstation equipment as necessary.
  • Documentation Management:
    Maintain documentation of helpdesk interactions including details of enquiries, troubleshooting steps and resolutions to facilitate knowledge sharing and process improvement. Create and update Knowledge Base articles and how‑to training materials.
  • Communication:
    Respond to all tickets, inquiries, and incidents in a thorough, careful, efficient manner, using proper grammar and spelling, a kind helpful tone, respecting the company’s vision and values.
  • Inventory Management:
    Maintain an accurate inventory of all hardware assets, supplies and software licenses.
  • User Account Management:
    Facilitate onboarding and offboarding of team members, including provisioning and deprovisioning of software accounts, access requests and additional software requests in line with IT policies.
  • Assist with basic team member training and “how to” guidance for in‑scope applications and systems.
  • Assist the testing and timely application of all critical software/Operating System updates and patches within the organization.
  • Provide evening and weekend on call coverage.
  • Manage vendors and MSPs delivering on‑site maintenance services, and work with other IT teams to ensure delivery of quality service.
  • Occasional travel to local restaurants for support or new deployments.
  • Assist in the creation of IT Operations processes and procedures, ensuring adherence to operational KPIs and SLAs.
What You’ll Need:
  • 3+ years of experience working on a corporate helpdesk.
  • Adaptability and learning. Willingness to adapt to new technologies, and keep pace with changes in Restaurant technology.
  • Hardware:
    Demonstrable understanding of desktops, laptops, POS devices, networking, and peripherals.
  • Excellent troubleshooting skills including the ability to systematically identify and follow a set of steps to resolve a problem or incidents.
  • Excellent customer service skills, and a passion for helping others.
  • Strong knowledge & proficiency of Microsoft desktop environments and software…
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