Automation Scripting Jobs in Sycamore, IL (NOW HIRING)

Automation Specialist  

What this role will entail:

The Automation 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. You’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 — 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 – 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

• 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