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.
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Senior Windows Server Automation Engineer in Toronto employer: Swoon
Swoon is an exceptional employer that fosters a collaborative and innovative work culture in the heart of Toronto. As an Appian Tech Lead, you will not only have the opportunity to lead and mentor a talented team but also benefit from professional growth through hands-on development and strategic leadership. With a focus on employee well-being and career advancement, Swoon offers a dynamic environment where your contributions directly impact the success of the enterprise solutions we deliver.
