Senior Systems Engineer

Role: VMware-to-Hyper-V Migration SME / Senior Systems Engineer

Location: Madison, WI
Duration: 6 Months
Start: August 18 19, 2026
Client: Confidential Professional Association
Work Arrangement: ideally 2 days onsite in Madison during the week of August 17
Payment: Bi-weekly, Paid When Paid

Job Summary

Seeking a VMware-to-Hyper-V Migration SME / Senior Systems Engineer to lead a production infrastructure migration from VMware to Microsoft Hyper-V. The candidate must have hands-on experience completing actual production VMware-to-Hyper-V migrations, not just separate VMware and Hyper-V administration experience.

Required Skills

• VMware: Strong production administration experience with VMware ESXi and vCenter
• VMware-to-Hyper-V Migration: Proven experience planning and executing production VM migrations from VMware to Microsoft Hyper-V
• Migration Planning: Ability to assess VMware environments and develop phased migration plans minimizing downtime and operational risk
• Hyper-V: Experience building/configuring Hyper-V hosts and target environments
• Windows Server: Experience migrating and validating Windows Server workloads
• Virtual Networking: Strong knowledge of VLANs, virtual switches, DNS, IP addressing, and network dependencies
• Storage: Understanding of virtual storage and infrastructure dependencies
• Backup & Recovery: Experience with backup, replication, recovery, and rollback strategies
• Production Validation: Ability to validate compute, storage, networking, security, applications, and performance after migration
• Troubleshooting: Ability to resolve networking, storage, driver, performance, and application issues
• Project Ownership: Ability to independently own the migration, identify risks, recommend solutions, and communicate with IT leadership
• Availability: Able to start quickly and support a time-sensitive infrastructure transition

Nice-to-Have Skills

• Veeam backup, replication, recovery, or migration
• Wasabi / S3-compatible cloud storage
• Microsoft SQL Server
• Microsoft Intune
• Microsoft Entra ID
• F5 load balancing / application delivery
• Windows Systems Administration
• On-premises + externally hosted infrastructure
• Managed service providers / vendors such as CDW
• Infrastructure documentation, migration runbooks, validation procedures, and operational handoff

Key Responsibilities

• Assess existing VMware hosts, VMs, storage, networking, applications, and dependencies
• Design/refine the Hyper-V target environment
• Develop and execute a phased VMware-to-Hyper-V migration
• Configure Hyper-V, networking, storage, and related components
• Migrate production workloads and coordinate migration windows
• Validate applications, databases, networking, backups, and recovery
• Establish rollback/recovery procedures
• Troubleshoot migration issues
• Document the new environment and provide knowledge transfer