Senior Windows Engineer

Swoon; Toronto; On-site; CAD 110,000 - 150,000; Full time

Job summary

Swoon is seeking an experienced Senior Windows Engineer to join our Windows Engineering team. The role focuses on designing enterprise Windows standards, automation playbooks, and serving as a Level 3 escalation point for complex issues in financial services environments.

You will develop standards, write PowerShell modules and Ansible playbooks, and guide Build and Operations teams with advanced technical expertise.

Qualifications

• 5+ years of Windows Server experience (2016/2019/2022).
• Strong understanding of Group Policy Objects (GPOs).
• Experience with Windows clustering deployments including SQL Server clusters.
• Hands-on SAN storage concepts and solutions in Windows environments.
• Advanced proficiency in PowerShell scripting and automation.
• Experience with OS deployment standards and automation frameworks.
• Security-focused with knowledge of baselining and hardening in financial services.

Responsibilities

• Design and develop enterprise Windows standards and guidelines.
• Create automation playbooks and PowerShell modules for standardization.
• Design and implement Ansible playbooks for Windows automation.
• Lead and mentor Level 1/2 staff; provide escalation support.
• Collaborate with enterprise architecture on infrastructure roadmaps.
• Partner with security/compliance teams on baselines and governance.

Skills

Windows Server

Group Policy

Windows Clustering

SAN Storage

Automation

PowerShell

OS Deployment

Escalation Support

Virtualization

Security

Education

Bachelor's degree in Computer Science/IT

Tools

Ansible

HP Server Automation (HPSA)

Data Center Automation (DCA)

VMware vSphere

Active Directory

Azure/AWS

Job description

We are seeking an experienced Senior Windows Engineer to join our Windows Engineering team. The successful candidate will be responsible for developing enterprise Windows standards, creating automation playbooks, and serving as a Level 3 escalation point for complex technical issues. This role focuses on designing solutions and standards that are implemented by Build teams and supporting Operations teams with advanced technical expertise in financial services environments.

KEY ACCOUNTABILITIES

• Standards & Architecture: Design and develop enterprise Windows infrastructure standards and best practices
• Create comprehensive technical documentation and implementation guidelines
• Define security baselines and configuration standards for Windows environments
• Collaborate with enterprise architecture teams on infrastructure roadmap planning
• Automation & Playbook Development: Develop and maintain advanced PowerShell scripts and modules for standardized automation
• Design and create Ansible playbooks for Windows environment automation to be executed by Build teams
• Build reusable automation frameworks and templates for OS deployment and configuration
• Create infrastructure-as-code standards and provide guidance to implementation teams
• Level 3 Technical Support & Escalation: Serve as subject matter expert for complex Windows infrastructure issues escalated from Operations teams
• Provide advanced troubleshooting and root cause analysis for critical incidents
• Develop solutions for recurring operational challenges and performance issues
• Mentor and provide technical guidance to Level 1 and Level 2 support staff
• Security & Compliance: Partner with Enterprise Protect team to develop security standards, frameworks, and hardening baselines appropriate for financial services environments
• Collaborate on compliance guidelines and configuration standards for industry regulations (SOX, PCI-DSS, etc.)
• Establish patch management standards and procedures for operational teams to execute
• Provide technical guidance to implementation teams on security standard deployment
• Collaboration & Leadership: Partner with Build teams to ensure successful implementation of automation playbooks and standards
• Collaborate with Operations teams to understand operational challenges and develop solutions
• Work with cross-functional teams including network, security, and application teams on standards alignment
• Provide technical mentorship and knowledge transfer to implementation and operations teams
• Participate in change advisory boards and technical design reviews
• Document standards, procedures, and troubleshooting guides for operational teams

EXPERIENCE & EDUCATION

Technical Skills

• Windows Expertise: 5+ years of experience with Windows Server (2016/2019/2022)
• Group Policy: Strong understanding of Group Policy Objects (GPOs) with experience creating, managing, and troubleshooting complex policy implementations
• Windows Clustering: Experience with Windows Server failover clustering deployments including MS SQL Server clusters
• SAN Storage: Understanding of Storage Area Network (SAN) concepts with hands‑on experience implementing SAN solutions in both bare metal and virtualized Windows environments
• Automation: Advanced proficiency in Ansible for Windows automation and configuration management
• HPSA/DCA: Experience with HP Server Automation (HPSA) or Data Center Automation (DCA) is highly desired
• Scripting: Expert‑level PowerShell scripting skills with experience in complex automation scenarios
• Deployment Standards: Experience designing OS deployment standards and automation frameworks for implementation by other teams
• Escalation Support: Experience providing Level 3 technical support and complex issue resolution
• Virtualization: Experience with VMware vSphere, Hyper‑V, or other virtualization platforms
• Security: Knowledge of Windows security frameworks, hardening standards, and security tools

Industry Experience

• Financial Services: Minimum 3 years of experience in financial industry IT environments
• Compliance: Understanding of financial industry regulations (SOX, PCI-DSS, etc.)
• Risk Management: Experience with change management processes and risk assessment procedures

Professional Skills

• Best Practices: Demonstrated knowledge of ITIL, infrastructure best practices, and enterprise architecture principles
• Team Collaboration: Proven ability to work effectively in team environments and mentor junior staff
• Problem Solving: Strong analytical and troubleshooting skills with attention to detail
• Communication: Excellent verbal and written communication skills

Preferred Qualifications

• Bachelor's degree in Computer Science, Information Technology, or related field
• Microsoft certifications (MCSA, MCSE, or equivalent)
• Experience with cloud platforms (Azure, AWS) and hybrid environments
• Knowledge of container technologies (Docker, Kubernetes)
• Understanding of network protocols and Active Directory services