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Helpdesk Technician-Tier 2

Frankfort, IL
  • Expired: October 08, 2022. Applications are no longer accepted.


Are you a perfectionist who enjoys following directions? Do you need variety and change to keep from getting bored? Do you agonize over details and making sure all your work is perfect? Do you enjoy solving problems? Are you a team player whose first question is "How can I help you?" Do you enjoy juggling multiple tasks?


  • Address issues that have been escalated
  • Perform remote troubleshooting
  • Determine the best solution based on the issue and details provided by customers
  • Walk the customer through the problem-solving process
  • Record notes regarding the issue and troubleshooting taken
  • Create and maintain documentation
  • Follow-up and update customer with status and information
  • Identify and suggest possible improvements on procedures

System Requirements:

  • 2+ year experience as a Helpdesk Technician (preferably an MSP)
  • Good understanding of computer systems, servers, and networking
  • Passionate (and patient) about problem solving and customer service.
  • Diligent with note taking, following process, and documentation.
  • Driven to learn more, stay positive, and grow; not only as a team member but in all of life.
  • CompTia A+ and Net+ certifications are a plus!

About us and what you can expect:
LeadingIT provides fully outsourced cybersecurity and IT support to growth focused Chicagoland businesses and organizations.  We break the typical mold by providing ALL-inclusive FAST + FRIENDLY support to our clients with a focus on SECURITY.

We have a fast-paced environment with ZERO micro managing, we assess RESULTS.
We gather feedback and adjust how we operate based on YOUR ideas.
We CARE about our team and our clients and understand the need for flexibility with life+work.

TWO great locations within <8 minute walk of Metra UPNW line in Woodstock, IL AND downtown Chicago OR the ability to work from home/anywhere.

Your benefits -

Salary: $52,000+/year based on your experience and work ethic
Our ascension plans, even for Level 1, provide more than $10,000+/year in upward mobility
100% company paid health, dental, life, and vision benefits
Company match 5% 401k plan with Guideline
More than 14+ days of paid time off AND two weeks' vacation
Company provided HP notebook, iPhone, and company gear

Our hiring process:

Submit your application AND complete a communication survey (7 min).
If we like what we see, we will reach out to schedule a phone interview (20 min).
If that goes well, we'll schedule a technical interview (1 hour).

For a more in depth look at our hiring timeline check out



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Desired salary* Do you have experience with email management and in Exchange, Office 365, or Gsuite?* Have you performed any server or email migrations? Please provide details.* Do you have experience with Connectwise and LabTech?* -- No answer --YesNo Do you have a minimum of 3 years MSP experience?* -- No answer --YesNo Please list technical certifications you have received* Submit Application



Frankfort, IL