About the Engagement

A large enterprise is migrating a mission-critical warehouse and manufacturing operations platform from on-premises VMware infrastructure to AWS. This role focuses on the Windows Server infrastructure layer executing server migrations, file share migrations, OS replatforming, and network connectivity validation for the 20 Windows Server hosts and 152 storage volumes that support the application

The migration strategy uses Zerto as the primary replication platform (with AWS MGN as a secondary option) for continuous data replication and orchestrated cutover. The first phase targets the QA environment, followed by production migrations to support international facilities. This role is front-loaded the bulk of the work completes before production cutover, with a brief stabilization period afterward.

This is an embedded engineer role the successful candidate will work directly alongside the Cloud Infrastructure team, the application team, and the Zerto/migration tooling specialists to execute the lift-and-shift migration of Windows Server workloads.

Key Responsibilities
Server Migration Execution
Execute Windows Server migrations from on-premises VMware to AWS EC2 using
Zerto as the primary replication platform (with AWS MGN as fallback option)
Manage Zerto VPG (Virtual Protection Group) configuration, replication orchestration, and failover/failback testing
Plan and execute OS replatforming from Windows Server 2012 R2 to Windows Server 2022 where required
Validate application compatibility before and after OS replatforming, working closely with the application team
Remove VMware Tools and on-premises-specific agents post-migration; validate AWS Systems Manager agent installation and reporting
File Share Migration
Migrate large shared file mounts (terabyte-scale SMB/NFS shares) to AWS FSx for Windows File Server or Amazon EFS
Design and execute data sync strategy with minimal downtime during cutover windows
Validate SMB/NFS connectivity from AWS EC2 instances to migrated file shares
Ensure continued connectivity to on-prem physical hardware (barcode scanners, laser cutters, label printers) via file share access during and post-migration
Coordinate with enterprise file services team if shared mounts span multiple applications

Networking & Security
Collaborate with the Cloud Infrastructure team to validate security group rules based on port dependency analysis
Validate network preflight connectivity tests across all dependencies prior to each cutover
Configure hybrid networking (VPN, Transit Gateway, or Direct Connect) to maintain on-prem connectivity during migration
Troubleshoot SMB, RDP, and Windows service connectivity issues post-migration
Document security group inbound/outbound rules for Windows workloads

Database Connectivity Validation
Validate MSSQL Server connectivity from migrated Windows hosts to dependent database servers
Work with the DBA team to ensure application database connections (MySQL and MSSQL) are functional post-migration
Test and document connection strings, ODBC/JDBC connectivity, and authentication mechanisms in AWS
Required Qualifications
5+ years of experience in Windows Server infrastructure and enterprise migrations
Hands-on experience with Zerto for VMware-to-cloud migrations, including VPG configuration, failover/failback orchestration, and journal-based replication
Proficiency with Windows Server 2012 R2 and 2022 administration: Active Directory, SMB/CIFS, IIS, Windows services, and Group Policy
Experience migrating SMB file shares to AWS FSx for Windows File Server (terabyte-scale preferred)
AWS networking proficiency: VPC design, Security Groups, Transit Gateway, and hybrid connectivity (VPN/Direct Connect)
Experience designing and executing migration cutover plans with defined rollback criteria
Strong troubleshooting skills for Windows networking (SMB, RDP, firewall rules, DNS)
Excellent communication and stakeholder management skills able to coordinate across infrastructure, application, and DBA teams

Preferred Qualifications
Experience with AWS Application Migration Service (MGN) as a secondary migration tool option
Familiarity with Amazon EFS for NFS workloads
Experience with DFS (Distributed File System) replication and namespace management
Understanding of Windows Server licensing models (BYOL vs. License Included on EC2)
Experience with Infrastructure as Code: Terraform or AWS CloudFormation for EC2 and FSx provisioning
AWS certifications: Solutions Architect Associate or SysOps Administrator Associate
Familiarity with AWS Systems Manager for patch management and remote administration
Experience with vulnerability scanning tools and remediation workflows

Working Knowledge (Nice to Have)
Manufacturing, warehouse, or fulfillment center operational systems domain context
Understanding of physical hardware connectivity via SMB file shares (barcode scanners, laser cutters, label printers)
AWS Backup policies and snapshot management for EC2 and FSx
PowerShell scripting for Windows automation and configuration management
MSSQL Server connectivity troubleshooting (not DBA-level, but connection validation)
AWS Cost Optimization: Reserved Instances, Savings Plans, right-sizing for Windows workloads