Senior Windows Server Automation Engineer

Senior Windows Server Automation Engineer - Contract - Hybrid, Toronto (Financial District)

Our client - one of Canada’s Big 5 banks - is hiring a Senior Windows Server Automation Engineer for their Windows Engineering team. This is a hands-on, automation-first role: you’ll spend your time designing and building reusable, production-grade automation, not chasing tickets. If you write Ansible and/or Python like a developer - modular, idempotent, source-controlled, tested - and you know Windows Server infrastructure cold, this is built for you.

What you’ll do

• Design, develop, and maintain reusable, production-grade automation using Ansible and/or Python for end-to-end server lifecycle: OS deployment across physical and virtual environments, configuration, domain integration, security hardening, compliance validation, and patch readiness.
• Apply real software-engineering practice - source control, modular/idempotent design, testing, logging, error handling, secrets management, code review, and CI/CD. PowerShell where it makes sense for Windows integration.
• Design, automate, and troubleshoot enterprise Group Policy and Windows Server security baselines across a large estate, with targeted rollout, drift detection, and remediation.
• Lead performance analysis, complex troubleshooting, and root-cause resolution across OS, virtualization, storage, networking, identity, and security.
• Own technical designs and production outcomes, review code, and work across infrastructure, security, and operations teams.

What you bring

• 8+ years engineering and supporting large, complex enterprise Windows Server environments (physical, virtual, hybrid).
• Substantial, hands-on experience independently building and maintaining reusable automation in Ansible and/or Python - frameworks, roles, playbooks, modules, or tooling - with strong engineering discipline (source control, testing, CI/CD).
• Advanced Group Policy and Active Directory depth (OUs, inheritance/precedence, WMI and security filtering, delegation, conflict resolution) plus hands-on security-baseline design and automation.
• Core Windows infrastructure strength: failover clustering, Kerberos, certificates, patching, and vulnerability remediation.
• Working networking knowledge (TCP/IP, DNS, DHCP, subnetting, routing, load balancers) and performance tuning with tools like PerfMon and WPR/WPA.

Nice to have

• Microsoft, Red Hat Ansible, or Python certification.
• VMware/Hyper-V, cloud, and regulated-enterprise (financial services) experience.

Hybrid role (2-3 days/week onsite) based in downtown Toronto (Financial District). Contract. Compensation: $120,000–$130,000 annually, commensurate with experience.