Cloud Migration Engineer

We are seeking a senior technical expert with deep Windows engineering experience to support application teams as they migrate diverse Windows-based workloads (including homegrown applications, commercial off-the-shelf (COTS) products, and legacy services) into modern AWS-hosted environments. As a Cloud Migration Engineer, you will play a critical role in developing test plans, validating application behavior in new environments, externalizing configuration, troubleshooting migration issues, and teaching teams how to operate successfully in their target cloud environment.

You will work directly with engineering and product teams to clarify dependencies, modernize operational practices, and reduce risk through structured testing and deep technical guidance. Your work ensures that migrated applications are reliable, supportable, and aligned with enterprise standards.

·       Develop and execute detailed test plans for Windows-based workloads including: COTS applications, IIS/.NET services, Windows services, scheduled tasks, and SQL-connected systems. Validate functionality, configuration, networking, authentication, and performance in the target AWS environment.

·       Lead hands-on migration execution, assisting teams with installation validation, connectivity testing, functional smoke tests, configuration extraction, externalizing environment-specific settings, and resolving issues involving registry keys, service identities, permissions, certificate stores, firewall rules, DNS, authentication, and other Windows platform dependencies.

·       Teach, coach, and support application teams by explaining root causes, guiding them through remediating environment differences, helping redesign configuration models to be portable, and mentoring teams in operational best practices, troubleshooting techniques, and cloud-aligned patterns.

·       Improve migration consistency by creating scripts, runbooks, and repeatable validation steps for common Windows issues such as missing dependencies, blocked ports, legacy configuration paths, local account usage, registry drift, and environment inconsistencies.

·       Collaborate cross-functionally with infrastructure, security, and network teams to align migration prerequisites, resolve cross-cutting issues, and help standardize practices for identity, logging, monitoring, access, and AMI lifecycle.

·       Independently handle complex technical issues with minimal supervision, while escalating only the most complex or systemic issues to specialized teams.

·       Other duties as assigned.

·       Bachelor’s degree in a related field or equivalent experience

·       Confirmed experience troubleshooting Windows Server environments, including application services, configuration management, SQL connectivity, certificate stores, and Active Directory integration

·       Demonstrated experience supporting cloud-hosted Windows workloads (AWS, Azure, or similar)

·       Practical experience diagnosing network issues such as firewall rules, security groups, DNS, routing, and port-level connectivity

·       Minimum of four years of related work experience

·       Other minimum qualifications may apply

·       Experience migrating COTS applications to AWS, including handling installers, licensing models, vendor-defined configuration, and environment prerequisites

·       Strong proficiency with Windows diagnostic tools (Event Viewer, PerfMon, Resource Monitor, Services MMC, Registry Editor, IIS Manager when applicable) and network troubleshooting tools (netsh, Test-NetConnection, nslookup, PowerShell networking utilities)

·       Experience analyzing AWS networking constructs to resolve connectivity and hybrid networking issues

·       Experience establishing effective monitoring, logging, and observability practices to support post-migration reliability

·       Ability to coach application teams through dependency mapping, configuration externalization, troubleshooting exercises, and reducing machine-specific behavior

·       Familiarity with PowerShell for automation, diagnostics, and configuration extraction

·       Experience resolving common migration blockers such as hardcoded paths, installer prerequisites, registry-only configuration models, licensing constraints, legacy authentication challenges, and complex service dependencies