Career Listing


Senior Helpdesk Technician

Peotone, IL · Full-time · Experienced

About The Position

Helpdesk Technician-Tier 3

Level 3 Technician

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?

What this role will entail:

  • Solve uncommon issues that have been escalated
  • Perform remote network and server troubleshooting
  • Learn and integrate new security technologies
  • Determine the best solution based on the issue and details provided by customers
  • Handle project implementation from start to finish
  • Record notes regarding the issue and troubleshooting taken
  • Create and maintain documentation
  • Follow-up and update customer with status and information

What we need from you (system requirements):

  • Driven to succeed at work and in all of life, hard work required
  • ACCOUNTABLE to our clients as well as our company 
  • Keep a POSITIVE mindset with a solution focus. 
  • Desire for EXCELLENCE in what we do, all day every day. 
  • HUMBLY CONFIDENT you can make it happen, and if not, able to ask for help.  
  • Proven experience as a help desk technician or other customer support role
  • Good understanding of computer systems, mobile devices, and other tech products
  • Ability to diagnose and resolve basic technical issues
  • 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!
  • 2+ year of MSP experience REQUIRED

More about us and where we are going:

Our goal is to become the BEST cybersecurity and IT provider across Chicagoland. We PROTECT growing Chicagoland organizations from malicious cybersecurITy threats and subpar nickel + dime IT support. We have doubled our company (team of 40+ with 200+ clients) in the last two years and will continue to grow at fast pace – planning to triple across the next three years.

  • We have a fast-paced environment with ZERO micromanaging, 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.

THREE great locations in Woodstock, IL as well as downtown Chicago (both are just off Metra UPNW line) and Manteno, IL and/or some flexibility to work from anywhere.

Our all-inclusive total compensation and benefits package for this role includes:

  • Salary is based on your experience, drive and the value you can bring our company; and is in the range of $60,000 to $70,000
  • Ascension plan if applicable
  • We provide 100% company paid health, dental, life, and vision benefits – value of $4,500 to $14,000/year
  • We match 5% of your contributions to Guideline 401k – value of 5% of salary.
  • Unlimited PTO policy
  • Company provided gear (notebook + iPhone) as well as company clothing.

Our hiring process:

  • Submit your application
  • AND complete a communication survey (7 min) REQ’D (Please check your spam folder. Sometimes the email goes there instead of your inbox.)
  • If we like what we see, we will reach out to schedule a video interview

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

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