Join a team that wants to solve IT right 100% of the time

We understand that to take care of our clients, we first have to take care of our team. We are a values driven workplace, where we solve the unsolvable, and we strive to provide concierge support to all of our clients. 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

  • Driven

    DRIVEN to succeed at work and in all of life, hard work required. Our company continues to grow based on the growth of our team and us as individuals – in business and life. We work hard each day every day to fuel our clients

  • Accountable

    ACCOUNTABLE to our clients as well as our company. We run our company by numbers and we are accountable to our clients. We hold each other accountable as well as OWNING our mistakes and making IT right if we mess up.

  • Positive/Fun/Mindset

    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

    Desire for EXCELLENCE in what we do, all day every day. We strive to be the best for our company, for our team, and for each of our clients.

  • Humbly confident

    HUMBLY CONFIDENT you can make it happen, and if not, able to ask for help. We continue learning so we can confidently solve problems as our field constantly changes. Yet we aren’t afraid to ask for help when needed.


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

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Full Health Insurance

(Regardless of coverage type Employee Only-Family) We pay 100% of the premium for medical, dental, vision and life insurance
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5% match
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My Time Off Policy - Unlimited Days

9 paid Holidays, 7 sick days, and Unlimited PTO (available to be used after 90 days of employment)
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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 Certifications

We pay for your job-related certifications and training materials. Once the certification is received, you will also receive a salary increase

Automatic COLA Raises

We give a .875% COLA raise every quarter

Anniversary Bonuses

($100 for every year of service)

Fitness Incentives

Receive up to $150 reimbursement for a fitness watch. Annual Fitness initiatives

Bench 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.

Bench Ascension Plan

Level 1 Ascension Plan

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

Level 2 Ascension Plan

Level 2 Technician
  • Datto DCAT

    $1000 Salary Increase

  • Fortinet NSE4

    $2500 Salary Increase

  • HPE Switch Configuration

    $2000 Salary Increase

  • CompTIA Server+

    $1500 Salary Increase

  • HPE Server/Data Solutions

    $2000 Salary Increase

  • Complete a Migration Project

    $2000 Salary Increase

Our Hiring Process

  • 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.