Systems Administrator; Windows Server Migration

Job Title:

Systems Administrator – Windows Server Migration

Location:

Toronto, ON (4x onsite a week)

Employment Type:

Contract

Pay Rate: CAD $45 - $50/HR INC

Interview Type:
Face to Face (Onsite Interview Only)

We are seeking two experienced Systems Administrators to join our IT development team for a critical Windows Server migration project. You will be responsible for programmatically migrating legacy systems from Windows Server 2019 to Windows Server 2022, ensuring minimal downtime and maintaining system integrity. This is a hands‑on technical role requiring strong scripting automation skills and experience with enterprise migration projects.

• Develop automated scripts and procedures for migrating Windows Server 2019 environments to Windows Server 2022
• Migrate and configure legacy VB components, ASP applications, and .NET web services
• Register all required certificates
• Transition Windows services, scheduled tasks, and batch jobs to the new environment
• Create comprehensive migration documentation and rollback procedures
• Collaborate with development teams to troubleshoot application compatibility issues
• Implement monitoring and validation processes to ensure successful migration
• Maintain system security and compliance standards throughout the migration process
• Provide post‑migration support and optimization

• 5+ years experience in Windows Server administration (2016/2019/2022)
• Expert‑level scripting abilities with Power Shell for automation and migration tasks
• Proficiency with additional scripting languages (Bash, Python, or similar)
• Hands‑on experience with IIS configuration and migration (IIS 10 to IIS 11)
• Proven experience migrating legacy applications including:
• VB6 components and ASP classic applications
• .NET Framework web applications and web services
• Windows services and scheduled tasks
• Strong knowledge of batch job migration and task scheduler management
• Experience with server imaging, cloning, and configuration management
• Understanding of Active Directory, DNS, DHCP, and other core Windows services

• Knowledge of containerization (Docker) for legacy application isolation
• Familiarity with CI/CD pipelines for deployment automation
• Experience with monitoring tools (Dynatrace, Zabbix, or similar)
• Understanding of networking concepts and firewall configuration
• Previous experience with data center migrations or cloud migrations

• Bachelor’s degree in Computer Science, Information Technology, or equivalent experience
• Proven track record of successful enterprise‑scale migration projects
• Ability to create detailed technical documentation and procedures
• Strong problem‑solving skills and ability to troubleshoot complex system issues
• Excellent communication skills for collaborating with technical and non‑technical stakeholders
• Relevant Microsoft certifications (MCSE, MCSA) preferred but not required
• Experience working in Agile/Scrum project environments

• Experience with phased migration approaches and cutover planning
• Knowledge of dependency mapping for interconnected systems
• Ability to work with legacy systems while planning modernization pathways
• Experience with testing methodologies for migration validation
• Understanding of business continuity planning during migration activities