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LeadingIT

IT Services and IT Consulting

We partner with Chicagoland businesses to solve all of their IT issues with unlimited 24/7 support and a local dedicated crew.

Is LeadingIT hiring?

Yes. As of November 4, 2026, LeadingIT has 32 open roles on Metaintro. 6 were posted in the last 30 days.

Open roles

Newest first. Pay shown when the posting lists it.

Hiring pattern

How fast LeadingIT is adding roles, and how they're set up.

New roles each monthRoles first posted in the month

23
3
1
10
0
JulyAugustSeptemberOctoberNovember
November: 0 new roles.

How roles are set upShare of open roles

50%
43%
7%
HybridOn-siteNot stated
50% of roles are hybrid or remote.

Customers

The company LeadingIT names as a customer.

Customers1

  • Cathy

What their customers say

Quotes from people at LeadingIT's customers.

“We are delighted with the performance, responsiveness, strategic coordination, and cost effectiveness of Leading IT. They should be on your short list if you are in need of top notch IT services at a very attractive price point. Give them a call!”

Tim

“We are replacing much of our IT infrastructure and Leading IT's practice of including projects in the base monthly cost has been a major time and money saver. I was skeptical whether this practice was to good to be true - it wasn't. They have delivered on every promise.”

Tim

“We brought Leading IT on board 5 months ago and cannot say enough good things about that decision. Our aging senior living center was struggling with technology demands and outdated equipment. Leading IT assessed our needs quickly and helped draw us a road map to a better future state. Their approach is organized, well thought out, and sensitive to budget constraints. Service has been prompt, effective, and always very courteous.”

Tim

“I can't say enough positive things about LeadingIT. They have been able to resolve issues that our former "big" MSP dropped the ball on or couldn't figure out. We're now focused on getting our mis-managed SharePoint straight. It's gong to be a BIG job, but I have all the confidence that we'll finally be on the right track!”

“LeadingIT is great to work with. All of their technicians are very knowledgeable and the one I have worked with the most is Geovel Operana. He is very fast and very good at his job. He fixes all our issues in a timely manner and very pleasant to talk to.”

Show 12 more quotes

“They are great at following up to make sure everything is working correctly.”

“I loved working with LeadingIT. Always quick and friendly service.”

“Working with LeadingIT has been tremendous. They handle situations immediately, they’re efficient, and our employees know exactly who to call when issues come up. Our team can focus on their jobs, and we can rely on LeadingIT to handle the technology. Stephen and Laura are tremendous and a pleasure to work with. LeadingIT is a partner that truly goes above and beyond”

““LeadingIT’s bench techs are the ones that typically visit our office when we need support. They’re super nice and professional, and always get back to me with knowledgeable input about my request for assistance. As a financial institution, we have to deal with a lot of private information from our clients. Knowing that our problems are resolved immediately and our systems are constantly monitored is a huge relief.””

Suzie · CEO

““LeadingIT covers everything, from phones, to computers, to printers. Their availability, knowledge, and customer support has been a great help. Five-star service all the way. Our company has been with LeadingIT from the beginning and couldn’t be happier. The staff is friendly and knowledgeable. The service is fast and accurate. I have challenged them over the years and they have yet to disappoint me. I recommend their services every chance I get.””

Al · Director of Operations

““I like how all-inclusive LeadingIT’s services are, and that they’ve had technical expertise in every area we’ve requested. Whether it’s network security, hardware, or managing updates with third party software providers, they’ve always provided great service! I have peace of mind knowing our systems are monitored 24/7, and that LeadingIT is always responsive to our needs in a timely manner.””

Scott · Executive Director

““We engaged LeadingIT over 11 years ago to take over day-to-day IT and help desk management. LeadingIT is a professional organization that takes the hassle out of keeping our workstations updated and network secure. They get the job done each and every time.””

Michael · Assistant Village Manager

“We engaged Stephen and his staff over 6 years ago to take over day-to-day IT and help desk management. LeadingIT is a professional organization that takes the hassle out of keeping our workstations updated and network secure. They get the job done each and every time.”

Michael

“LeadingIT is a trusted partner. They’re patient, kind, and always focused on solutions. I know if something breaks, it’ll be fixed fast—and explained in a way we can understand.”

“We don’t want to worry about computer problems when we already have a million other things to manage. The last thing our chief wants is to deal with technology issues. LeadingIT’s quick responsiveness and 24-hour support are invaluable—it’s a huge benefit to our organization”

“Working with LeadingIT has been a game changer. The team is accessible, personable, and incredibly responsive. Every problem gets solved—there’s no ‘we don’t know.’ Most of the time, it feels like they’re waiting on me with the ticket, rather than the other way around. It truly feels like they are on-site with us, and we value their partnership immensely”

“LeadingIT makes everything easy so I can focus on operations instead of IT fires. I know their techs by name and can have productive conversations anytime. They actively listen, offer valuable insight, and take cybersecurity as seriously as we do.”

Interviews

How LeadingIT describes its hiring process.

“Once we receive your application, it will be reviewed within 3 days of submission.”

Skills they ask for

Most frequent across open postings.

Most requested skills

  • CompTIA certifications
  • Accounts Receivable
  • Excel
  • Reconciliations
  • QuickBooks Online
  • Financial Reporting
  • Payroll
  • Accounts Payable
  • Troubleshooting
  • ConnectWise
  • RMM
  • Procurement

Tech stack

Analytics
Google Analytics 4
Google Tag Manager
Libraries
jQuery
Tailwind CSS
CMS
WordPress
CDN
unpkg

Company facts

Headquarters
Chicago, US
Founded
2010
Industry
IT Services and IT Consulting
Sector (NAICS)
Professional, Scientific, and Technical Services
Peer
HPE
Social
LinkedIn · X · YouTube · Facebook

Roles by location

Where LeadingIT is hiring. Pick a city to see its roles.

Similar companies

Companies in the same industry as LeadingIT that are hiring now.

Questions about LeadingIT

Is LeadingIT hiring?
Yes. As of November 4, 2026, LeadingIT has 32 open roles on Metaintro. 6 were posted in the last 30 days. The most are in Tech General (18), Sales (6), and Finance (4).
Where is LeadingIT hiring?
LeadingIT is hiring in Woodstock, Manteno, Chicago, Bourbonnais, Naperville, and Peotone, with the most open roles in Woodstock.
Does LeadingIT offer remote or hybrid work?
50% of open roles are hybrid and 0% are remote.
What is the interview process at LeadingIT?
LeadingIT describes it this way: “Once we receive your application, it will be reviewed within 3 days of submission.”
Who are LeadingIT's customers?
LeadingIT names 1 customer, including Cathy.
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