Windows System Engineer

Senior Windows Infrastructure Migration Engineer

6+ Month Contract (with potential extension)

Work Hours: Monday-Friday, 8:00 AM - 5:00 PM

Work Arrangement: Hybrid - minimum 2-3 days per week onsite

Benefits: Medical, dental, and vision benefits included

Please Note: Not open to Third-Party Firms and candidate must reside in the Charlotte, NC area.

We are seeking a senior-level Windows Infrastructure Migration Engineer to support enterprise modernization efforts focused on upgrading legacy Windows Server environments. This role is hands-on and execution-driven, centered on migrating business-critical applications and services from Windows Server 2008 to newer supported versions (2019 / 2022) within an IaaS environment. This is not a software development role. The focus is on operating system upgrades, IIS-hosted applications, Windows Services, and legacy infrastructure dependencies.

Key Responsibilities

• Migrate applications and server workloads from Windows Server 2008 to Windows Server 2019/2022
• Lead and execute IIS website migrations, including application pools, bindings, authentication, and certificates
• Migrate and validate Windows Services, including service accounts, permissions, and startup dependencies
• Assess and support SQL Server application dependencies such as connection strings, service accounts, and permissions
• Evaluate and migrate message queues (MSMQ or equivalent technologies)
• Identify migration risks, compatibility issues, and remediation pathsDocument existing environments, migration steps, and post-migration configurations
• Collaborate with infrastructure, DevOps, and application teams during planning and execution
• Troubleshoot and resolve post-migration issues in production and non-production environments

Required Skills & Experience

• 8+ years of hands-on Windows infrastructure experience
• Proven experience migrating Windows Server workloads from legacy to modern versions
• Strong IIS administration and application migration experience
• Solid experience with Windows Services configuration and troubleshooting
• Practical SQL Server knowledge from an application dependency standpoint
• Experience working with MSMQ or similar enterprise queuing technologies
• Strong troubleshooting, root-cause analysis, and documentation skills
• Working knowledge of Microsoft technologies (.NET applications from a hosting perspective)
• Familiarity with Active Directory and networking fundamentals

Nice-to-Have

• PowerShell scripting for automation or configuration Exposure to CI/CD tools (e.g., TeamCity, Octopus Deploy)
• Azure IaaS familiarity
• Experience working in change-controlled enterprise environments
• Security awareness in regulated systems

Soft Skills

• Clear and effective communication
• Ability to work independently while collaborating across teams
• Detail-oriented and methodical approach to migration work
• Strong troubleshooting mindset
• Willingness to learn legacy environments and undocumented systems

Onboarding Requirements
Employment is contingent upon successful completion of a background check and drug screening.