LeadingIT Jobs Hiring Now
LeadingIT is hiring for 11 open roles on Migrate Mate as of July 16, 2026, concentrated in growth marketing and IT support. Migrate Mate updates LeadingIT's live openings daily. LeadingIT is a managed IT services and technology support provider serving businesses in the Chicago metropolitan area.
Find LeadingIT JobsOverview
LeadingIT hiring data on Migrate Mate, as of July 16, 2026.
- Open jobs
- 11
- Top team
- Growth Marketing
- Seniority
- Across all levels
- Work type
- 0% remote or hybrid
- Top location
- Woodstock
Open Roles at LeadingIT
Showing 11 of 11+ LeadingIT jobs
IT Field Technician
What this role will entail:
Are you a perfectionist who enjoys following directions? Do you need variety and change to keep from getting bored? Do you agonize over details and making sure all your work is perfect? Do you enjoy solving problems? Are you a team player whose first question is “How can I help you?” Do you enjoy juggling multiple tasks?
Accountabilities:
- Handling a massive variety of client support requests from a diverse client base
- Hardware deployment to clients
- PC Imaging
- Determine the best solution based on the issue and details provided by customers
- Travel on-site to clients organization
- Follow-up and update customer status and information
- Identify and suggest possible improvements on procedures
- Walk the customer through the problem-solving process
Indicators that this will be the role for you:
- Proven experience as a help desk technician or other customer support role
- Good understanding of computer systems, mobile devices, and other tech products
- Ability to diagnose and resolve basic technical issues
- Passionate (and patient) about problem solving and customer service.
- Diligent with note taking, following process, and documentation.
- Driven to learn more, stay positive, and grow; not only as a team member but in all of life.
- CompTia A+ and Net+ certifications are a plus!
More about us:
At LeadingIT, our people and our culture are at the heart of everything we do. We are a growing, security-focused MSP that runs on the Entrepreneurial Operating System (EOS). This means clarity, accountability, and alignment are not buzzwords here. They are how we operate every single day. We want everyone on our team to live their EOS life, which means having the ability to do what you love, with people you love, while making a huge difference, being compensated appropriately, with time for other passions.
Our core values are not posters on the wall. They are who we are.
Accountable. Staying Positive. Chase Excellence. Driven. Humbly Confident.
If these values describe how you show up in your work and with your clients, you will fit right in here.
Our all-inclusive total compensation and benefits package for this role includes:
- Salary for this role is $42,500.
- Ascension plan if applicable
- We provide 100% company paid health, dental, life, and vision benefits – value of $4,500 to $14,000/year
- We match 5% of your contributions to Guideline 401k – value of 5% of salary.
- Open Door PTO policy
- Company provided gear (notebook + softphone) as well as company clothing.
Our hiring process:
- Submit your application
- If we like what we see, we will reach out to schedule a video interview
Additional Perks:
We’re building a company where success is shared. LeadingIT has committed to distributing $5 million in profit back to our team over the next 10 years—on top of fully paid benefits, unlimited PTO, and a people-first culture. We are building something that changes lives.
For a more in depth look at our jobs/benefits/hiring timeline check out www.goleadingit.com/careers
IT Field Technician
What this role will entail:
Are you a perfectionist who enjoys following directions? Do you need variety and change to keep from getting bored? Do you agonize over details and making sure all your work is perfect? Do you enjoy solving problems? Are you a team player whose first question is “How can I help you?” Do you enjoy juggling multiple tasks?
Accountabilities:
- Handling a massive variety of client support requests from a diverse client base
- Hardware deployment to clients
- PC Imaging
- Determine the best solution based on the issue and details provided by customers
- Travel on-site to clients organization
- Follow-up and update customer status and information
- Identify and suggest possible improvements on procedures
- Walk the customer through the problem-solving process
Indicators that this will be the role for you:
- Proven experience as a help desk technician or other customer support role
- Good understanding of computer systems, mobile devices, and other tech products
- Ability to diagnose and resolve basic technical issues
- Passionate (and patient) about problem solving and customer service.
- Diligent with note taking, following process, and documentation.
- Driven to learn more, stay positive, and grow; not only as a team member but in all of life.
- CompTia A+ and Net+ certifications are a plus!
More about us:
At LeadingIT, our people and our culture are at the heart of everything we do. We are a growing, security-focused MSP that runs on the Entrepreneurial Operating System (EOS). This means clarity, accountability, and alignment are not buzzwords here. They are how we operate every single day. We want everyone on our team to live their EOS life, which means having the ability to do what you love, with people you love, while making a huge difference, being compensated appropriately, with time for other passions.
Our core values are not posters on the wall. They are who we are.
Accountable. Staying Positive. Chase Excellence. Driven. Humbly Confident.
If these values describe how you show up in your work and with your clients, you will fit right in here.
Our all-inclusive total compensation and benefits package for this role includes:
- Salary for this role is $42,500.
- Ascension plan if applicable
- We provide 100% company paid health, dental, life, and vision benefits – value of $4,500 to $14,000/year
- We match 5% of your contributions to Guideline 401k – value of 5% of salary.
- Open Door PTO policy
- Company provided gear (notebook + softphone) as well as company clothing.
Our hiring process:
- Submit your application
- If we like what we see, we will reach out to schedule a video interview
Additional Perks:
We’re building a company where success is shared. LeadingIT has committed to distributing $5 million in profit back to our team over the next 10 years—on top of fully paid benefits, unlimited PTO, and a people-first culture. We are building something that changes lives.
For a more in depth look at our jobs/benefits/hiring timeline check out www.goleadingit.com/careers
Job Roles at LeadingIT
Working at LeadingIT
LeadingIT's 11 open roles are across all levels, and about 0% are remote or hybrid. The most active teams are growth marketing, IT support, and compliance & risk. LeadingIT is a managed IT services and technology support company offering network administration, cybersecurity, and technology solutions to small and mid-sized businesses. The team includes both technical roles such as network administrators and field technicians, and marketing roles spanning strategy, digital content, and automation. Most LeadingIT roles are based in Woodstock and Manteno.
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Browse jobs by roleLeadingIT Jobs: Frequently Asked Questions
How many jobs is LeadingIT hiring for right now?
LeadingIT is hiring for 11 open roles on Migrate Mate as of July 16, 2026, updated daily, concentrated in growth marketing and IT support. The current openings span both technical and marketing disciplines, making LeadingIT one of the more broadly hiring technology services firms on Migrate Mate at the moment.
What kinds of roles does LeadingIT hire for?
The most active teams are growth marketing, IT support, and compliance & risk. LeadingIT hires across IT and networking roles such as field technicians, network administrators, and AI solutions specialists, alongside marketing roles including marketing managers, marketing assistants, and digital marketing interns. Most postings are across all levels, covering both early-career and experienced candidates.
Are LeadingIT jobs remote or in-person?
Mostly on-site. About 0% of LeadingIT's open roles on Migrate Mate are remote or hybrid as of July 16, 2026, with the rest based in Woodstock. Each LeadingIT listing shows its work location so you can filter before applying.
How do I apply to a job at LeadingIT?
Find a LeadingIT role on Migrate Mate, then follow the listing through to LeadingIT's own application portal to submit your materials. LeadingIT manages its own hiring process, so all applications, follow-ups, and interview scheduling happen directly with the LeadingIT team.
Does LeadingIT hire entry-level?
Most of LeadingIT's open roles on Migrate Mate are across all levels as of July 16, 2026. Check individual LeadingIT listings for stated experience requirements.
Where is LeadingIT hiring?
Most LeadingIT roles are based in Woodstock and Manteno, and about 0% offer remote or hybrid work as of July 16, 2026. Migrate Mate shows the location on each listing.