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 workplace, 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).

📌 Senior Windows System Engineer (Toronto)
🏢 Swoon
📍 Toronto