IT Generalist (Tier 2 Helpdesk)

The IT Generalist (Tier 2 Helpdesk) provides advanced technical support across a wide range of systems, applications, and infrastructure. This role serves as the escalation point for Tier 1 technicians, resolving complex issues, maintaining core IT systems, and ensuring reliable day‑to‑day operations for end users. The ideal candidate is a versatile problem‑solver with strong troubleshooting skills, excellent communication and custom service, and the ability to work independently in a fast‑paced environment. Reports directly to IT Director. This role is in-person at our corporate office in Burr Ridge, IL.

Schedule: Monday-Friday (8:30am-5pm); on call requirement once every 3 weeks

Specific Duties

  • Resolve escalated incidents related to hardware, software, networking, and user accounts.
  • Troubleshoot issues involving Windows 11, Microsoft 365, VPN, printers, and line‑of‑business applications.
  • Provide remote and on‑site support for end users.
  • Complete new user logins and terminations.
  • Complete new user training.
  • Familiar with internet service providers and service set up for the opening of new office locations
  • Participate in patching, security, and system hardening efforts leveraging RMM tools configuration baselines
  • Assist with IT projects, documentation, upgrades, and deployments
  • Monitor refrigeration temperatures.
  • Adhere to HIPAA and PCI security standards
  • Follow least-privilege access controls and secure configuration practices
  • Participate in security awareness and incident response procedures
  • Other duties and tasks as assigned.

Requirements

Education and Relevant Job Experience:

  • Associate’s or Bachelor’s in IT preferred.
  • Minimum of 3-4 years of help desk experience.
  • Comfortable in fast-paced, multi-site environments
  • On-call coverage

Physical Requirements:

  • Ability to use a computer and telephone
  • Requires prolonged sitting
  • Ability to lift and move 50 lbs

Benefits

  • Health Insurance
  • Dental insurance
  • Vision insurance
  • Disability insurance
  • Life insurance
  • Paid time off
  • 401(k)- Profit Sharing

Salary

  • $68,000-$75,000/year
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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...

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