Simply Smart Now Part of LeadingIT Learn more

Join a team that is at the forefront of cybersecurity

Are you looking for a company who cares about their employees? Do you excel at delivering top-notch customer service? Are you ready to grow and learn from an experienced team? We would love for you to join our team!

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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

  • We are driven
    to make IT happen

  • We consistently

  • We go farther as a
    cohesive team

  • We fuel amazing
    client satisfaction


Enjoy company provided HP notebook, iPhone, and company gear plus these awesome perks:

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Full Health Insurance

100% company paid health, dental, life, and vision benefits for employee and family
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5% match
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More than 14+ days of paid time off AND two weeks vacation
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Yearly Raises

Our ascension plans, even for Level 1, provide more than $10,000+/year in upward mobility
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Free Lunch

Fully stocked kitchen with all the lunch essentials. Lunch provided by a local restaurant for Friday Team lunch
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Paid Certification

We pay for your job related certifications and training materials

Level 1 Ascension Plan

We highly encourage continuing education because technology is always changing. Check out our ascension plans to see how you can grow with LeadingIT.

Junior Level 1 Technician
  • A+ Certification

    $1000 Salary Increase

  • Network + Certification

    $2000 Salary Increase

  • 1 year experience
    with LeadingIT

Senior Level 1 Technician
  • Microsoft Office 365 Certification

    $2500 Salary Increase

  • Close 50+ Tickets A Week for 30 Days

    $2000 Salary Increase

  • No Negative Smile Backs for 90 Days

    $2000 Salary Increase

  • New Employee Mentoring

    $2000 Salary Increase

Our Hiring Process

Every day we dedicate our attention and knowledge to provide best in class services and support to our clients. This dedication also leads to being recognized by industry leaders.

  • Step 1


    Once we receive your application, a link will be emailed to you to complete a communications survey. This will take about 7 minutes. This survey must be completed in order to qualify for a phone interview.

  • Step 2

    Phone Interview

    You will have a quick chat with our hiring manager to get to know you better.

    If you do not hear from us for a phone interview, do not let that discourage you from applying in the future.

  • Step 3 ?

    Technical Interview

    Congrats! You made it past the phone 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.

  • Step 4


    Pending on the position you applied for, we will have you come in for a trial OR a have you do a virtual lab test. This will give us a better understanding of your experience. This trial is paid and would be anywhere from 2-4 hours pending on your availability.

  • Step 5


    We like to be transparent with salary and it will be part of the 1st interview. The formal offer will come immediately after your trial/virtual lab test.

  • Step 6


    Welcome to the team!

Open positions

We are hiring! Apply today.