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.

KEY ACCOUNTABILITIES

·
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.

MINIMUM QUALIFICATIONS

·
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

PREFERRED QUALIFICATIONS

·
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