Windows Server Automation Lead (Ansible/Python)

S.I. Systems Ltd.; Toronto; On-site; CAD 110,000 - 130,000; Full time

Job summary

S.I. Systems Ltd. is seeking a Senior Windows Server Automation Engineer to design, implement, and maintain production automation for OS deployment and server configuration across physical, virtual, and hybrid environments.

The role emphasizes security baselines, Group Policy, and Active Directory, with hands-on expertise in Windows Server engineering. You will lead complex automation projects, mentor engineers, and collaborate with infrastructure, security, and operations teams to ensure

Qualifications

• Substantial experience designing, developing, testing, debugging, and maintaining reusable, production-grade automation code.
• Proven automation of OS deployment across physical/virtual environments and domain integration.
• Hands-on Windows Server engineering across large, enterprise environments.
• Strong experience with Group Policy, AD, and security baselines.
• Proficient in networking, DNS/DHCP, VLANs, and firewall/load balancers.
• Ownership of complex designs, mentoring, and cross-team communication.

Responsibilities

• Design, develop, and maintain production-grade automation using Ansible/Python for OS deployment and server configuration.
• Integrate automation with APIs, CMDB, and orchestration platforms.
• Define standards for secure, scalable Windows Server platforms across environments.
• Implement and automate enterprise GP and AD baselines with proper controls.
• Lead performance analysis and issue resolution across OS, hardware, virtualization, and network layers.
• Own designs, review code, and mentor engineers across multiple teams.

Skills

Automation Development

Server Lifecycle

Windows Server Eng

Group Policy & AD

Networking

Performance Optimization

Core Windows Infra

Ownership & Mentoring

Education

Bachelor’s degree in CS/IT/Engineering

Microsoft/Red Hat Ansible or Python certs

Tools

VMware

Hyper-V

Cloud platforms

Job description

S.I. Systems Ltd. is seeking a Senior Windows Server Automation Engineer to design, implement, and maintain production automation for OS deployment and server configuration across physical, virtual, and hybrid environments.

The role emphasizes security baselines, Group Policy, and Active Directory, with hands-on expertise in Windows Server engineering. You will lead complex automation projects, mentor engineers, and collaborate with infrastructure, security, and operations teams to ensure