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Leadingit Jobs (NOW HIRING)

LeadingIT

Helpdesk Technician - Tier 1

Manteno, IL ยท On-site

$40K - $50K/yr

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 ...

Apply Early

LeadingIT

Level 1 Helpdesk Technician

Manteno, IL ยท On-site

$40K - $50K/yr

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 ...

Apply Early

LeadingIT

Field Technician

Manteno, IL ยท On-site

$42K/yr

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 ...

Apply Early

LeadingIT

Systems Administrator

Woodstock, IL ยท On-site

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 ...

LeadingIT

Network Administrator

Woodstock, IL ยท On-site

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 ...

LeadingIT

Helpdesk Technician - Tier 1

Woodstock, IL ยท On-site

$40K - $50K/yr

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 ...

LeadingIT

Field Technician

Manteno, IL ยท On-site

$42K/yr

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 ...

Apply Early

LeadingIT

Automation Specialist

Woodstock, IL ยท On-site

$65K/yr

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 ...

LeadingIT

Microsoft Solutions Specialist

Woodstock, IL ยท On-site

$65K/yr

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 ...

Apply Early

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Showing results 1-20

All JobsLeadingit Jobs

Leadingit information

See salary details

$40K

$93.6K

$116.5K

How much do leadingit jobs pay per year?

As of Jul 7, 2026, the average yearly pay for leadingit in the United States is $93,575.00, according to ZipRecruiter salary data. Most workers in this role earn between $91,500.00 and $103,500.00 per year, depending on experience, location, and employer.

What is the difference between Leadingit vs Network Administrator?

AspectLeadingitNetwork Administrator
Required CertificationsITIL, PMP, CompTIA Security+CompTIA Network+, Cisco CCNA
Work EnvironmentProject-based, strategic planning, leadership rolesNetwork setup, maintenance, troubleshooting
Employer & Industry UsageIT consulting firms, large corporationsIT departments, service providers
Common Search & ComparisonLeadership, strategic IT managementNetwork infrastructure, technical support

Leadingit roles focus on strategic IT leadership, project management, and guiding teams, often requiring certifications like PMP. Network Administrators handle network setup, maintenance, and troubleshooting, with certifications like CCNA. While both work in IT, Leadingit positions are more strategic and managerial, whereas Network Administrators are more technical and operational.

What are the key skills and qualifications needed to thrive as an IT Lead, and why are they important?

To thrive as an IT Lead, you need strong technical expertise in IT infrastructure, project management, and a relevant degree, often supported by certifications like CompTIA, Cisco, or PMP. Familiarity with systems such as network management tools, cloud platforms (e.g., AWS, Azure), and security frameworks is typically required. Exceptional communication, leadership, and problem-solving skills help in managing teams and coordinating projects effectively. These skills and qualities are crucial for ensuring reliable IT operations and successful implementation of technology initiatives.

What are some of the main challenges faced by someone in a Leading IT role, and how can they be overcome?

Professionals in a Leading IT role often face challenges such as managing diverse teams, aligning technology strategies with business goals, and staying updated on rapidly evolving technologies. Balancing day-to-day operations with long-term IT planning can also be demanding. To overcome these challenges, effective communication, continuous learning, and strong project management skills are essential. Collaborating closely with other departments and fostering a culture of innovation can help ensure IT initiatives deliver real business value.

What are Leadingit professionals?

Leadingit professionals are experts specializing in the management and leadership of information technology (IT) teams and projects. They are responsible for overseeing IT operations, implementing technology strategies, and ensuring that IT systems align with the organization's goals. Their role typically involves coordinating between technical staff and business leaders, managing budgets, and ensuring the security and efficiency of IT infrastructure. Leadingit professionals often hold positions such as IT managers, directors, or chief information officers (CIOs).
More about Leadingit jobs
What cities are hiring for Leadingit jobs? Cities with the most Leadingit job openings:
What states have the most Leadingit jobs? States with the most job openings for Leadingit jobs include:
What job categories do people searching Leadingit jobs look for? The top searched job categories for Leadingit jobs are:
Leadingit jobs near you
Infographic showing various Leadingit job openings in the United States as of July 2026, with employment types broken down into 90% Full Time, and 10% Part Time. Highlights an 100% Physical job distribution, with an average salary of $93,575 per year, or $45 per hour.
Microsoft AI Solutions Specialist

Microsoft AI Solutions Specialist

LeadingIT

Woodstock, IL โ€ข On-site

$65K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted 20 days ago

Job description

Microsoft AI Solutions Specialist

What this role will entail:

๏ปฟThe Microsoft AI Solutions Specialist is responsible for solving operational and technical challenges through smart automation. This role blends systems thinking, technical expertise, and a passion for continuous improvement. Youโ€™ll work cross-functionally to eliminate repetitive tasks, integrate tools, and enable scalability through automation.

Accountabilities:

  • Proactively identify process inefficiencies and create automated solutions
  • Build and manage automations across tools like Power Automate, Zapier, ConnectWise Automate, and through custom scripting (e.g., PowerShell, Python)
  • Integrate internal and client-facing platforms using APIs, webhooks, and middleware
  • Lead automation initiatives for tasks like ticket routing, reporting, alert escalation, and documentation syncs
  • Document all workflows and automation logic in a clear, supportable format
  • Reduce Staffing Costs Through Scalable Automation
  • Build automation solutions that directly eliminate repetitive, labor-intensive tasks โ€” creating capacity within existing teams
  • Monitor and maintain automation stability and performance
  • Partner with service, operations, and leadership teams to prioritize high-impact improvements
  • Integrate Systems Across the MSP Stack
  • Create seamless, secure connections between tools (PSA, RMM, documentation, cloud platforms) using APIs, scripting (PowerShell, Python), and platforms like Power Automate or Zapier to reduce swivel-chair work and duplicate data entry.

Requirements

  • 2+ years in a role focused on technical automation, scripting, or process engineering
  • Advanced problem-solving ability with a strong attention to detail
  • Familiar with Powershell
  • Experience with Microsoft 365, Copilot, cloud automation, and API integrations
  • Experience with MSP environments and tools like ConnectWise, IT Glue, etc.
  • Experience with RMM/PSA tools (ConnectWise Automate, Manage)
  • Knowledge of security-focused automation (e.g., SIEM, SOAR tools)
  • Reswt experience

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 position is $65k/annually.
  • We provide 100% company paid health, dental, life, and vision benefits โ€“ value of $4,500 to $14,000/year
  • We match 5% of your contributions to Guideline 401k โ€“ 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:

Weโ€™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 yearsโ€”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


Requirements:
  • 2+ years in a role focused on technical automation, scripting, or process engineering
  • Advanced problem-solving ability with a strong attention to detail
  • Familiar with Powershell
  • Experience with Microsoft 365, Copilot, cloud automation, and API integrations
  • Experience with MSP environments and tools like ConnectWise, IT Glue, etc.
  • Experience with RMM/PSA tools (ConnectWise Automate, Manage)
  • Knowledge of security-focused automation (e.g., SIEM, SOAR tools)
  • Reswt experience