Senior Windows System Engineer

Job Title: Senior Windows Engineer (Infrastructure & Automation)

Location: Toronto, ON (Hybrid)

Employment Type: Full-Time

Compensation: $120K-$130K +bonus+ benefits

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: Strong 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).