Senior Windows System Engineer

Toronto, ON
Hybrid
Posted Oct 17, 2026
1 position

$120,000–$130,000 / year

Opens LinkedIn

Employment type: Full-time
Experience level: Senior · 5+ years
Minimum education: Bachelor’s degree
Posting language: English
Working hours: 40 hours per week
Seniority: Mid-Senior level
Application method: Direct apply is available

Job summary

Design enterprise Windows standards, security baselines, and automation playbooks using PowerShell and Ansible for large-scale infrastructure. Provide Level 3 escalation and root-cause analysis while ensuring integration with virtualization, clustering, directory, networking, and storage services and compliance with regulatory and change-management requirements.

Job details

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).

What you’ll do

Requirements

Requires 5+ years of enterprise Windows Server experience, advanced PowerShell and Ansible automation skills, and experience with VMware clustering, Windows Failover Clustering, Active Directory, storage, and networking. Also requires at least 3 years in financial services or another regulated environment; a bachelor’s degree in a related field is preferred.