Senior AWS Migration Specialist Engineer - VMware to AWS || Remote (DC/Maryland/Virginia)

We are seeking a Senior AWS Migration Specialist Engineer to lead end-to-end migration of our on-premises VMware virtual machine estate to AWS. You will own the technical execution of the full migration program — from discovery and landing-zone build through wave-based cutover and VMware decommissioning — working across a program expected to run 3–18 months with a 30–90 day dual-run period where on-premises and cloud run in parallel.

You will act as the senior technical authority for a cross-functional migration team (PMO, sysadmins, DevOps/SRE, network engineers, security/compliance), applying the playbook's six-phase model: Foundation → Connect → Identity → Pilot → Waves → Exit.

Windows/Linux VMs on VMware; AD/DNS/DHCP strategy; file services; hybrid networking (Direct Connect / Site-to-Site VPN); wave planning; cutover; rollback; hypercare; decommissioning.

Application rewrites; VDI farm redesigns; mainframe / proprietary appliances without a cloud path; legal e-discovery holds (coordinate Legal).

Reporting line: Head of Cloud / Infrastructure Engineering, with dotted-line program reporting to the Migration PMO.

Design and deploy the AWS landing zone: multi-account structure via AWS Control Tower / AWS Organizations, account vending, OU design, guardrails, centralized logging (audit + logging accounts per the Control Tower landing-zone model).

Establish the AWS support plan, tagging standards, cost allocation, and the program RACI matrix; ensure the exit criteria “accounts live, logging on, RACI signed” are met before any workload moves.

Own the migration cost model: build TCO / dual-run cost sketches from the discovered VM inventory, validated against the AWS Pricing Calculator and Enterprise Discount Program rates.

Category	Requirement
Experience	7+ years in infrastructure engineering, with 3+ years hands-on delivering large-scale (100+ VM) VMware-to-AWS migrations.
Migration tooling	Deep production experience with AWS Transform MGN / Application Migration Service, including agent-based replication, replication templates, test/cutover lifecycle, and rollback. Familiarity with legacy CloudEndure / SMS lineage is a plus — current MGN is the operating standard.
Discovery & assessment	Production use of AWS Application Discovery Service (ADS), AWS Migration Hub, and Migration Evaluator; ability to build dependency maps and heat-scored wave plans.
VMware expertise	5+ years administering vSphere / ESXi / vCenter: vMotion, DRS, linked clones, RDM, distributed vSwitch, NSX, vSAN — sufficient depth to anticipate migration-blocking edge cases.
Hybrid networking	Direct Connect, Site-to-Site VPN, Transit Gateway, hybrid DNS (Route 53 Resolver endpoints), and BGP routing.
Windows / Linux	Strong OS-level migration skills on both platforms, including AD / DC placement, DHCP / DNS strategy, and guest-agent / PV driver conversion.
Databases	Experience with AWS DMS for RDS / Aurora targets and schema conversion fundamentals.
IaC & automation	Terraform and/or CloudFormation / CDK; strong scripting in PowerShell and Python (the playbook's inventory / wave / validation / cost scripts are the working toolkit); CI/CD familiarity.
Governance	Experience writing and operating runbooks, RACI matrices, CAB / change approvals, wave plans, and rollback drills.
Certifications	AWS Certified Solutions Architect – Professional (required within 6 months of hire if not held); at least one of: AWS Advanced Networking – Specialty, AWS DevOps Engineer – Professional.

• Experience with the sister VMware-to-Azure migration path or other cloud exit / entry patterns (multi-cloud fluency).

• AWS Certified Migration Architect, or AWS Well-Architected review facilitation experience.

• Cost optimization track record: EDP negotiation inputs, AWS Pricing Calculator modeling, dual-run cost containment.

• Compliance environment experience (HIPAA / PCI / SOX / ISO 27001) and encryption- / key-management design (KMS, HSM).

• Containerization / Kubernetes exposure (EKS) for workloads selected for replat forming rather than rehosting.

• Prior technical-lead role across multi-team programs with executive reporting.

Program-level communication: translate technical cutover risk into GO/NO-GO language for CAB and executives.

Cross-functional leadership: coordinate sysadmins, network engineers, DevOps/SRE, and security without direct authority.

Crisis composure: own the freeze window, the rollback call, and the 2 a.m. cutover bridge calmly.

Documentation discipline: every wave leaves behind evidence — validation of output, RTO measurement, updated CMDB.

Pragmatic risk judgment: decommission is irreversible; insist on evidence + retention policy before exit.