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Job Title: Zerto - Windows Infrastructure & Migration Engineer- Remote EST hours

Duration: 6 months with possible extension

Location: Remote

The Windows role requires expert Zerto VPG configuration for VMware-to-AWS migrations, terabyte-scale SMB/FSx file share migrations, Windows Server 2012R2→2022 replatforming with app compatibility testing, and AWS hybrid networking depth.

Need someone who has done a VMware to AWS/EC2 lift and shift migration project. Ideally using Zerto. Experience migrating other technologies is irrelevant this is T3 doing this specific migration.

· 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

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

Area Rating Hands on Exp

Zerto & Migration Tooling (relaxed)

Post-Migration Cleanup & Validation

OS Replatforming (2012 R2 → 2022)

FSx & File Share Migration (relaxed)

Physical Hardware Connectivity (SMB/Warehouse)

Active Directory & Group Policy in AWS

DFS Knowledge

AWS Networking & Security Groups

Migration Planning & Runbooks

Cross-Team Coordination

Windows Server Licensing (BYOL/LI)

PowerShell & Automation

IIS & Application Validation

AWS Cost Optimization

Communication & Client Readiness

Thank you,

Shiva Mittal