Senior Windows Server Automation Engineer

S.I. Systems Ltd.; Toronto; Presencial; CAD 110.000 - 130.000; Jornada completa

Descripción de la vacante

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

Formación

• 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.

Responsabilidades

• 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.

Conocimientos

Automation Development

Server Lifecycle

Windows Server Eng

Group Policy & AD

Networking

Performance Optimization

Core Windows Infra

Ownership & Mentoring

Educación

Bachelor’s degree in CS/IT/Engineering

Microsoft/Red Hat Ansible or Python certs

Herramientas

VMware

Hyper-V

Cloud platforms

Descripción del empleo

Senior Windows Server Automation Engineer

The Senior Windows Server Automation Engineer combines deep enterprise Windows Server engineering expertise with substantial hands-on experience independently designing, developing, testing, debugging, and maintaining production automation code using Ansible and/or Python. Key areas of responsibility include Group Policy, Active Directory, Windows Server security baselines, and end-to-end server lifecycle management, including OS deployment across physical and virtual environments, initial server configuration, compliance, performance optimization, and ongoing management. Success in this role requires demonstrated ownership of complex server platforms and reusable automation solutions throughout their lifecycle.

KEY ACCOUNTABILITIES

• Design, develop, and maintain reusable, production-grade automation using Ansible and/or Python for OS deployment across physical and virtual environments, including initial server configuration, domain integration, security hardening, compliance validation, patch readiness, and transition to ongoing management. Apply sound software-engineering practices, including modular and idempotent design, source control, testing, logging, error handling, secrets protection, rollback, code review, and CI/CD; use PowerShell where appropriate for Windows Server integration.
• Integrate automation with APIs, orchestration platforms, configuration-management systems, CMDB, and enterprise service-management platforms.
• Define and maintain engineering standards and supportable patterns for secure, scalable Windows Server platforms across physical, virtual, and hybrid environments throughout the server lifecycle.
• Design, implement, troubleshoot, and automate enterprise Group Policy and Windows Server security baselines, using Active Directory structures and controls to support targeted deployment, impact analysis, compliance validation, drift detection, exception handling, and remediation.
• Lead Windows Server performance analysis and optimization, complex troubleshooting, and root-cause resolution across operating system, hardware, virtualization, storage, networking, identity, security, and automation dependencies.
• Own technical designs and production outcomes, review code, mentor engineers, and communicate decisions, risks, and dependencies across infrastructure, security, application, and operations teams.

EXPERIENCE & EDUCATION

Required Qualifications

• Automation Development: Substantial experience independently designing, developing, testing, debugging, and maintaining reusable, production-grade automation code using Ansible and/or Python, with PowerShell applied as appropriate for Windows Server automation and integration. Experience should include frameworks, roles, playbooks, modules, integrations, or tooling and demonstrate strong engineering practices such as source control, modular and idempotent design, testing, logging, error handling, secrets management, code review, release management, and CI/CD.
• Server Lifecycle Management: Proven experience automating OS deployment across physical and virtual environments, including initial server configuration, domain integration, security hardening, compliance validation, and ongoing management.
• Windows Server Engineering: 8+ years of hands-on experience engineering and supporting large, complex enterprise Windows Server environments across physical, virtual, and hybrid platforms.
• Group Policy, Active Directory, and Security Baselines: Advanced experience designing, implementing, troubleshooting, and managing enterprise Group Policy, including inheritance, precedence, security and WMI filtering, delegation, controlled rollout, and policy conflict resolution. Working knowledge of Active Directory concepts relevant to Windows Server administration is required, including OUs, domain membership, authentication, service accounts, and delegation, together with experience designing, automating, validating, and maintaining Windows Server security baselines.
• Networking: Working knowledge of TCP/IP, IPv4/IPv6, subnetting, routing, VLANs, DNS, DHCP, firewalls, load balancers, ports, and protocols, with the ability to diagnose Windows Server connectivity, name-resolution, latency, packet-loss, and access issues.
• Performance Optimization: Experience baselining, analyzing, and tuning Windows Server CPU, memory, storage I/O, network, services, processes, and virtualization performance using tools such as PerfMon, Resource Monitor, and Windows Performance Recorder/Analyzer.
• Core Windows Infrastructure: Strong knowledge of Kerberos, certificates, failover clustering, server hardware, patching, and vulnerability remediation.
• Senior-Level Ownership: Demonstrated ability to lead complex designs and production issues independently, make sound technical decisions, provide Level 3 escalation support, and deliver durable solutions across multiple teams.

Preferred Qualifications

• Bachelor’s degree in Computer Science, Information Technology, Engineering, or equivalent relevant experience.
• Relevant Microsoft, Red Hat Ansible, or Python certification.
• Experience with VMware, Hyper-V, cloud platforms, and regulated enterprise environments.

Salary: 110,000-130,000

Disclaimer:
AI may be used in evaluating candidates.
This posting is for an existing vacancy.

Position Overview

The Senior Windows Server Automation Engineer combines deep enterprise Windows Server engineering expertise with substantial hands-on experience independently designing, developing, testing, debugging, and maintaining production automation code using Ansible and/or Python. Key areas of responsibility include Group Policy, Active Directory, Windows Server security baselines, and end-to-end server lifecycle management, including OS deployment across physical and virtual environments, initial server configuration, compliance, performance optimization, and ongoing management. Success in this role requires demonstrated ownership of complex server platforms and reusable automation solutions throughout their lifecycle.

KEY ACCOUNTABILITIES

• Design, develop, and maintain reusable, production-grade automation using Ansible and/or Python for OS deployment across physical and virtual environments, including initial server configuration, domain integration, security hardening, compliance validation, patch readiness, and transition to ongoing management. Apply sound software-engineering practices, including modular and idempotent design, source control, testing, logging, error handling, secrets protection, rollback, code review, and CI/CD; use PowerShell where appropriate for Windows Server integration.
• Integrate automation with APIs, orchestration platforms, configuration-management systems, CMDB, and enterprise service-management platforms.
• Define and maintain engineering standards and supportable patterns for secure, scalable Windows Server platforms across physical, virtual, and hybrid environments throughout the server lifecycle.
• Design, implement, troubleshoot, and automate enterprise Group Policy and Windows Server security baselines, using Active Directory structures and controls to support targeted deployment, impact analysis, compliance validation, drift detection, exception handling, and remediation.
• Lead Windows Server performance analysis and optimization, complex troubleshooting, and root-cause resolution across operating system, hardware, virtualization, storage, networking, identity, security, and automation dependencies.
• Own technical designs and production outcomes, review code, mentor engineers, and communicate decisions, risks, and dependencies across infrastructure, security, application, and operations teams.

EXPERIENCE & EDUCATION

Required Qualifications

• Automation Development: Substantial experience independently designing, developing, testing, debugging, and maintaining reusable, production-grade automation code using Ansible and/or Python, with PowerShell applied as appropriate for Windows Server automation and integration. Experience should include frameworks, roles, playbooks, modules, integrations, or tooling and demonstrate strong engineering practices such as source control, modular and idempotent design, testing, logging, error handling, secrets management, code review, release management, and CI/CD.
• Server Lifecycle Management: Proven experience automating OS deployment across physical and virtual environments, including initial server configuration, domain integration, security hardening, compliance validation, and ongoing management.
• Windows Server Engineering: 8+ years of hands-on experience engineering and supporting large, complex enterprise Windows Server environments across physical, virtual, and hybrid platforms.
• Group Policy, Active Directory, and Security Baselines: Advanced experience designing, implementing, troubleshooting, and managing enterprise Group Policy, including inheritance, precedence, security and WMI filtering, delegation, controlled rollout, and policy conflict resolution. Working knowledge of Active Directory concepts relevant to Windows Server administration is required, including OUs, domain membership, authentication, service accounts, and delegation, together with experience designing, automating, validating, and maintaining Windows Server security baselines.
• Networking: Working knowledge of TCP/IP, IPv4/IPv6, subnetting, routing, VLANs, DNS, DHCP, firewalls, load balancers, ports, and protocols, with the ability to diagnose Windows Server connectivity, name-resolution, latency, packet-loss, and access issues.
• Performance Optimization: Experience baselining, analyzing, and tuning Windows Server CPU, memory, storage I/O, network, services, processes, and virtualization performance using tools such as PerfMon, Resource Monitor, and Windows Performance Recorder/Analyzer.
• Core Windows Infrastructure: Strong knowledge of Kerberos, certificates, failover clustering, server hardware, patching, and vulnerability remediation.
• Senior-Level Ownership: Demonstrated ability to lead complex designs and production issues independently, make sound technical decisions, provide Level 3 escalation support, and deliver durable solutions across multiple teams.

Preferred Qualifications

• Bachelor’s degree in Computer Science, Information Technology, Engineering, or equivalent relevant experience.
• Relevant Microsoft, Red Hat Ansible, or Python certification.
• Experience with VMware, Hyper-V, cloud platforms, and regulated enterprise environments.

Salary: 110,000-130,000

Disclaimer:
AI may be used in evaluating candidates.
This posting is for an existing vacancy.