Oracle Cloud Infrastructure (OCI) Migration Specialist
Location: Remote – United States
Contract: 6 months + likely extension
Work Authorization: s / /– No Sponsorship
Schedule: Must overlap with US Pacific business hours; weekend/overnight cutover availability required
Job Overview
We are seeking an experienced Oracle Cloud Infrastructure (OCI) Migration Specialist to lead a hands-on Microsoft Hyper-V to OCI migration for a healthcare-adjacent nonprofit organization.
This is an engineering-focused role. The selected consultant will own the migration lifecycle including assessment, OCI landing-zone build, migration planning, replication, testing, production cutovers, rollback planning and hypercare.
The environment includes approximately 45 inventoried systems, with 19 confirmed workloads in scope. The estate includes Windows Server 2008 R2 through 2022, multiple Active Directory domains, physical servers, SQL Server and reporting workloads.
Key Responsibilities
Assess and document Windows/Hyper-V environments, dependencies, utilization and storage profiles.
Determine workload disposition including rehost, replatform, upgrade/rebuild, retain or retire.
Right-size OCI Compute and Block Volume resources based on measured workload requirements.
Build OCI landing zones including:
Tenancy and Compartments
VCNs and Subnets
Route Tables
Security Lists and NSGs
DRG
IAM Policies
OCI Vault
Configure IPSec Site-to-Site VPN and FastConnect connectivity.
Validate network latency, routing, firewall policies and DNS.
Design OCI-native backup, immutability and cross-region disaster recovery.
Migrate Hyper-V workloads to OCI using replication-based migration tools.
Perform seed replication, delta synchronization, test cutovers, production cutovers and failback.
Manage Active Directory migration activities including:
Domain Controllers
Replication
FSMO roles
DNS
Sites and Services
Address legacy Windows Server versions including 2008 R2, 2012 and 2012 R2 through upgrade, rebuild, migration or isolation.
Migrate physical Dell PowerEdge servers into OCI, including a SQL Server workload.
Develop detailed per-VM migration runbooks, acceptance criteria, rollback procedures and hypercare documentation.
Use PowerShell for repeatable administration and migration activities.
Use Terraform and/or OCI CLI for automation where applicable.
Required Qualifications
5+ years of experience migrating production Windows Server workloads to public cloud.
At least one completed end-to-end OCI migration that you can explain technically.
Strong hands-on Microsoft Hyper-V experience including:
Hyper-V hosts
Hyper-V clusters
VHD/VHDX
Live Migration
Export/Import
Strong practical experience with OCI:
Compute
Block Volume
Object Storage
VCN
DRG
Site-to-Site VPN
FastConnect
IAM
Vault
Cloud Guard
Experience with replication-based migration tools such as:
RackWare RMM, Carbonite/OpenText Migrate, Cristie, Zerto, or comparable technologies.
Strong Windows Server administration experience from 2008 R2 through 2022.
Active Directory migration/consolidation experience across multiple domains.
Knowledge of FSMO, DNS, replication topology and Sites and Services.
SQL Server migration fundamentals including backup/restore and Always On basics.
Strong networking knowledge including subnetting, routing, IPSec, firewall policies, DNS, certificates and IP re-addressing.
Strong PowerShell skills.
Terraform or OCI CLI experience is a strong plus.
Ability to create clear, executable technical migration runbooks.
Nice to Have
OCI Architect Associate or Professional certification.
HIPAA-regulated environment experience.
Healthcare/nonprofit experience.
Familiarity with BAA and PHI handling requirements.
Exchange Server migration/decommissioning.
Remote Desktop Services / Terminal Server migration.
Previous Hyper-V as the migration source rather than VMware.
Experience working as a subcontractor within a prime-contractor delivery model.
Important
Candidates must be:
Authorized to work in the United States without sponsorship.
Available for remote US work with Pacific business-hours overlap.
Available for occasional weekend/overnight migration cutover windows.
Able to provide a detailed walkthrough of a previous Hyper-V → OCI migration.
