Join a team that wants to solve IT right 100% of the time
Having Purpose at LeadingIT
Working at LeadingIT means joining a group of people obsessed with taking on the real challenge of cybersecurity and helping businesses across Wisconsin, Illinois and Indiana. With locations in Woodstock, Downtown Chicago and Manteno, IL we are the areas premier IT company with a positive team culture.
Our values guide us to always deliver our very best
Driven
Accountable
Stay Positive
Keep a POSITIVE mindset with a solution focus. We stay focused on solutions instead of the negatives. How we view is how we do.
Chase Excellence
Humbly Confident
Perks of Working at LeadingIT

Full Health Insurance

401k

My Time Off Policy – Unlimited Days

Yearly Raises

Free Lunch

Paid Certifications

Automatic COLA Raises

Anniversary Bonuses

Fitness Incentives

Mental Health Focused
LeadingIT holds the Bell Seal Certification. This award is a national certification program that recognizes employers who are committed to creating mentally healthy workplaces.

At LeadingIT, we use EOS, the Entrepreneurial Operating System, to keep our company running smoothly and our team aligned. It’s a simple set of tools and processes that helps us set clear goals, stay accountable, and keep everyone rowing in the same direction.
Why does this matter to you as a candidate? Because at LeadingIT, you’ll always know what success looks like, how your role contributes to the bigger picture, and where the company is headed. You’ll work with a leadership team that values transparency, clarity, and accountability and you’ll be part of a team that gets the right stuff done.
EOS helps us work smarter, grow faster, and build a culture where people actually enjoy showing up every day. We’re serious about performance, but we don’t take ourselves too seriously and we know that success starts with living our core values. If you’re someone who chases excellence, has drive, owns your stuff, stays positive, and brings a humble confidence to your work, there’s a good chance you’ll thrive here.
Employee Ascension Plans
We highly encourage continuing education because technology is always changing. Check out our ascension plans to see how you can grow with LeadingIT.
*Stipend remains as long as certification stays up to date/active.
Bench Tech
Click & Drag to explore Career Paths
L1 Tech Path
CompTIA A+ Cert
1 Year Experience with LeadingIT

Junior Level 1 Technician
Level 2 Field Engineer Path
CompTIA A+ Cert
1 Year Experience with LeadingIT
Senior Bench Technician
CompTIA Net+
1 Year Experience as Senior Bench Tech

Level 2 Field Engineer
Senior Level 1 Technician Path
CompTIA A+ Cert
1 Year Experience with LeadingIT
Senior Bench Technician
CompTIA Net+
Microsoft 365 Certification
1 Year Experience as Senior Bench Tech

Senior Level 1 Technician
Junior Level 1
Senior Level 1
MS-900 M365: Fundamentals
MS-102 M365: Administrator
Close 50+ Tickets A Week for 30 Days
No Negative Smile Backs for 90 Days

New Employee Mentoring
Level 2 Tech
MD-102 M365: Endpoint Administrator Associate
CompTIA Server+
MS-700 M365: Teams Administrator Associate
Fortinet Certified Professional
SC-300 Identity and Access Admin Associate

Complete a Migration Project
Application
Once we receive your application, it will be reviewed within 3 days of submission.
If we choose to proceed, you will receive 2 emails from us. One stating that we would like to set up the one-way video interview, and another with the link to complete the interview.
If you do not hear from us for a video interview, do not let it discourage you from applying in the future.
Video Interview
Once the one-video interview email is sent out to you, you will have 3 days to complete it. You will have a minute and a half to answer each question. You are able to preview and re-record a response, if need be, before submitting.
Once you have completed the video interview, the hiring manager will review your responses. We will reach out regardless of next steps.
Technical Interview
Congrats! You made it past the video interview. The next interview is a bit longer and a lot more technical. This interview will be conducted with the direct manager of the position you applied for.
Quick Chat
Once you have completed the technical interview, we’ll set you up with a quick, 15-minute chat with our company president.
Formal Offer
We like to be transparent with salary. All will be noted in the formal offer. The offer will come after your quick 15-minute chat.
You Join The Team
Our Hiring Process
Open positions
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Automation SpecialistOther · Full-time · Experienced
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Helpdesk Technician - Tier 1Cybersecurity · Full-time · Experienced
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Helpdesk Technician - Tier 3Cybersecurity · Full-time · Experienced
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Level 1 Helpdesk TechnicianCybersecurity · Full-time · Experienced
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Senior Helpdesk TechnicianCybersecurity · Full-time · Experienced
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Service Delivery ManagerOther · Full-time · Experienced
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Automation SpecialistOther · Full-time · Experienced
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Helpdesk Technician - Tier 1Cybersecurity · Full-time · Experienced
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Helpdesk Technician - Tier 3Cybersecurity · Full-time · Experienced
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Level 1 Helpdesk TechnicianCybersecurity · Full-time · Experienced
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Senior Helpdesk TechnicianCybersecurity · Full-time · Experienced
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Service Delivery ManagerOther · Full-time · Experienced
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Automation SpecialistOther · Full-time · Experienced
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Helpdesk Technician - Tier 1Cybersecurity · Full-time · Experienced
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Helpdesk Technician - Tier 3Cybersecurity · Full-time · Experienced
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Level 1 Helpdesk TechnicianCybersecurity · Full-time · Experienced
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Senior Helpdesk TechnicianCybersecurity · Full-time · Experienced
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Service Delivery ManagerOther · Full-time · Experienced
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Automation SpecialistOther · Full-time · Experienced
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Field Sales RepresentativeOther · Part-time · Entry-level
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Helpdesk Technician - Tier 1Cybersecurity · Full-time · Experienced
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Helpdesk Technician - Tier 3Cybersecurity · Full-time · Experienced
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Level 1 Helpdesk TechnicianCybersecurity · Full-time · Experienced
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Outside Sales ConsultantOther · Part-time · Entry-level
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Senior Helpdesk TechnicianCybersecurity · Full-time · Experienced
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Service Delivery ManagerOther · Full-time · Experienced