Windows Engineer

Swoon; Toronto; Hybrid; CAD 120,000 - 150,000; Full time

Job summary

Swoon is seeking an experienced Senior Windows Engineer to own the core Windows platform within a large enterprise, focusing on standards, security baselines, and automation. You will craft IaC playbooks in a lab setting for deployment by Build and Operations teams.

You will lead design and implementation of scalable Windows infrastructure, collaborate with security and architecture, and act as a Level 3 escalation for complex issues in a regulated financial services environment.

Qualifications

• 5+ years of hands-on enterprise Windows Server experience (2016/2019/2022).
• Advanced PowerShell scripting and Ansible playbooks for large-scale automation.
• VMware vSphere/ESXi multi-node clustering and Windows Failover Clustering.
• SAN storage concepts and core networking basics (DNS, DHCP, TCP/IP).
• 3+ years in financial services or regulated environments with PCI-DSS/SOX and change control.

Responsibilities

• Design enterprise Windows infrastructure standards, configuration guidelines, and security baselines for scale.
• Write advanced PowerShell scripts and design Ansible playbooks to automate OS deployments and configuration management.
• Serve as Level 3 escalation point and perform root-cause analysis for complex issues.
• Ensure integration across core services including VMware, AD, DNS, DHCP, and SAN storage.
• Collaborate with security and architecture teams to meet PCI-DSS/SOX and CAB change-management requirements.

Skills

Windows Server

PowerShell

Ansible

VMware vSphere

Windows Failover Clustering

Active Directory

GPOs

Education

Bachelor's degree in Computer Science/IT

Job description

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: 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).