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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 successes.

    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.

    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

    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.

    Perks of Working at LeadingIT

    Full Health Insurance

    (Regardless of coverage type Employee Only-Family) We pay 100% of the premium for medical, dental, vision and life insurance

    401k

    5% match

    My Time Off Policy – Unlimited Days

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

    Yearly Raises

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

    Free Lunch

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

    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
    Bell Seal Mental Health America 2025 Bronze award

    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.

    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

    3 Paths to Ascension

    Click & Drag to explore Career Paths

    L1 Tech Path

    CompTIA A+ Cert

    $1500 Salary Stipend*

    1 Year Experience with LeadingIT

    Junior Level 1 Technician

    Level 2 Field Engineer Path

    CompTIA A+ Cert

    $1500 Salary Stipend*

    1 Year Experience with LeadingIT

    Senior Bench Technician

    CompTIA Net+

    $1500 Salary Stipend

    1 Year Experience as Senior Bench Tech

    Level 2 Field Engineer

    Senior Level 1 Technician Path

    CompTIA A+ Cert

    $1500 Salary Stipend*

    1 Year Experience with LeadingIT

    Senior Bench Technician

    CompTIA Net+

    $1500 Salary Stipend*

    Microsoft 365 Certification

    $2500 Salary Stipend*

    1 Year Experience as Senior Bench Tech

    Senior Level 1 Technician


    Junior Level 1

    A+ Certification

    $1500 Salary Stipend*

    Network + Certification

    $1500 Salary Stipend*

    1 year experience with LeadingIT

    Senior Level 1

    MS-900 M365: Fundamentals

    $1500 Salary Stipend*

    MS-102 M365: Administrator

    $1500 Salary Stipend*

    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 Tech

    MD-102 M365: Endpoint Administrator Associate

    $2000 Salary Stipend*

    CompTIA Server+

    $1500 Salary Stipend*

    MS-700 M365: Teams Administrator Associate

    $2000 Salary Stipend*

    Fortinet Certified Professional

    $2500 Salary Stipend*

    SC-300 Identity and Access Admin Associate

    $2000 Salary Stipend*

    Complete a Migration Project

    $2000 Salary Increase
    Step 1

    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.

    Step 2

    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. 

    Step 3

    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.

    Step 4

    Quick Chat

    Once you have completed the technical interview, we’ll set you up with a quick, 15-minute chat with our company president. 

    Step 5

    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. 

    Step 6

    You Join The Team

    Welcome!

    Our Hiring Process