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

Skilled 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

📌 Senior Windows Engineer (Winnipeg)
🏢 Swoon
📍 Winnipeg