Job Level
Mid-LevelSenior
Tech Stack
AWSCloudDNSSQLVMware
About the role
- Lead and contribute to a large-scale Microsoft Server 2016 migration program across multiple environments
- Assess existing Windows Server 2016 infrastructure, applications, and dependencies to identify risks, remediation paths, and migration readiness
- Define and design migration strategies and roadmaps to ensure minimal disruption to business services
- Work closely with application owners and SMEs to validate compatibility, stability, and performance of workloads post-migration
- Develop detailed test plans, migration runbooks, rollback procedures, and technical documentation
- Perform technical proof-of-concepts (POCs), solution validations, and provide recommendations for migration approaches
- Collaborate with security teams to ensure migration activities align with corporate security standards and remediate vulnerabilities
- Provide technical expertise and act as a subject matter authority for Windows Server migrations within hybrid on-prem and cloud environments
- Support migration execution phases with troubleshooting, root cause analysis, and post-migration validation
- Mentor and provide knowledge transfer to operational support teams to ensure long-term sustainability of migrated environments
- Stay current with Microsoft lifecycle, Extended Security Updates (ESUs), and emerging technologies to inform migration planning
Requirements
- 6+ years of experience (Windows Migration Engineer)
- Strong expertise in Microsoft Windows Server (2012–2019) focusing on migration planning, design, and validation
- Hands-on experience with Active Directory, DNS, DHCP, Group Policy, and Certificate Services, including cross-version migrations
- Proven ability to work with large-scale environments (hundreds or thousands of servers), including dependency mapping and risk assessment
- Experience in developing and executing migration runbooks, rollback plans, and validation/testing frameworks
- Knowledge of Microsoft lifecycle management, including Extended Security Updates (ESUs), patching, and compliance considerations
- Practical understanding of SCCM / Endpoint Configuration Manager and automation tools for system upgrades and configuration deployment
- Familiarity with hybrid environments (on-premises and cloud, e.g., AWS) and workload migration strategies
- Awareness of security best practices, endpoint protection, and hardening standards during OS transitions
- Strong troubleshooting and problem-solving skills for compatibility and application stability issues during migration
- Ability to manage multiple concurrent workstreams and collaborate across infrastructure, application, and security teams
- Desirable knowledge of VMware virtualization platforms and SQL Server basics
- Ability to mentor and provide knowledge transfer to operational support teams
- Keyloop doesn’t require academic qualifications for this position; selection based on experience and potential, not credentials