Location:

Toronto, ON (Hybrid) Employment Type:

Full-Time Position Overview

We are seeking an experienced

Senior Windows Engineer

to join our enterprise Windows Engineering team in a financial services environment. The successful candidate will own the core Windows platform for a massive infrastructure environment, focusing on developing enterprise Windows standards, designing security baselines, building advanced automation playbooks (PowerShell & Ansible), and serving as a Level 3 escalation point for complex technical issues. This role sits squarely in proactive infrastructure architecture and automation. You will design standards and Infrastructure-as-Code (IaC) playbooks in a lab environment to be implemented by our Build and Operations teams. Key Accountabilities

Standards & Architecture:

Design enterprise Windows infrastructure standards, configuration guidelines, and security baselines for environments operating at scale. Automation & Playbook Development:

Write advanced, custom PowerShell scripts/modules and design Ansible playbooks from scratch to automate OS deployments and configuration management. Level 3 Technical Support & Escalation:

Act as the subject matter expert for complex, escalated Windows infrastructure challenges and perform root-cause analysis for critical incidents. Infrastructure & Virtualization:

Ensure seamless integration across core enterprise services,



including multi-node VMware vSphere clustering, Windows Failover Clustering, Active Directory, DNS, DHCP, and SAN storage concepts. Compliance & Risk Management:

Partner with security and architecture teams to ensure configurations adhere to strict regulatory compliance standards (e.g., PCI-DSS, SOX) and enterprise Change Management (CAB) protocols. Required Qualifications & Experience

Windows Server Expertise:

5+ years of hands-on enterprise experience with Windows Server (2016 / 2019 / 2022), Group Policy (GPOs), and Active Directory. Automation Mastery (Non-Negotiable):

Advanced proficiency in writing custom

PowerShell

scripts/modules and building

Ansible

playbooks from scratch for large-scale infrastructure automation. Virtualization & Clustering:

Solid foundational background in

VMware vSphere/ESXi

multi-node clustering and

Windows Failover Clustering

(including MS SQL clusters). Storage & Networking Fundamentals:

Solid understanding of SAN storage concepts and core networking fundamentals (DNS, DHCP, TCP/IP). Regulated Industry Experience:

Minimum 3 years of experience working in financial services or other highly regulated, secure enterprise environments, with deep familiarity with PCI-DSS, SOX, and strict change control procedures. Education:

Bachelor's degree in Computer Science, IT, or a related field (preferred).

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📌 Windows Engineer (Toronto)
🏢 Swoon
📍 Toronto