LeadingIT
Automation Specialist Other · Full-time · Experienced
LeadingIT, Chicago, Illinois, United States
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.
Key Responsibilities
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 and reducing the need for future headcount increases.
Monitor and maintain automation stability and performance
Partner with service, operations, and leadership teams to prioritize high-impact improvements
Requirements
2+ years in a role focused on technical automation, scripting, or process engineering
Advanced problem-solving ability with a strong attention to detail
Powershell competency is a must
Experience with Microsoft 365, cloud automation, and API integrations
Experience with MSP environments and tools like ConnectWise, IT Glue, etc.
Preferred (Nice-to-Haves)
Experience with RMM/PSA tools (ConnectWise Automate, Manage)
Knowledge of security-focused automation (e.g., SIEM, SOAR tools)
Understanding of EOS / Traction business framework
Our Core Values
Stay Positive – We bring a can-do attitude to every challenge.
Driven – We take ownership and push forward, no matter the obstacle.
Chase Excellence – We set high standards and constantly improve.
Accountable – We own our results and follow through.
Humbly Confident – We know our strengths and stay open to feedback
Ready to help a team that’s serious about doing things better?
Apply today and automate the future with LeadingIT.
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.
Partner Cross-Functionally to Drive Strategic Outcomes
Work closely with Service Delivery, Projects, and Leadership to identify high-impact automation opportunities that align with company goals, improve service experience, and reinforce LeadingIT’s values of excellence and accountability.
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