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Azure & On-Prem Server Upgrade Specialist

  • Location: Calgary

Posted 8 days ago

Job Title: Azure & On-Prem Server Upgrade Specialist (Hybrid Environment)
Job Type: 4-month contract (approx. 230 hours total)
Location: Calgary, AB (Hybrid)
Start Date: ASAP
Hours: 40 hours/week

Shift Schedule:  Monday–Friday, 9:00 AM – 5:00 PM)
Pay Rate: $75.00/hr T4 OR $90.00/hour Inc.




Role Overview
Our client is seeking an experienced Hybrid Infrastructure / Azure Specialist to support a critical server OS upgrade initiative within a mixed on-premises and cloud environment. This role will focus on upgrading Windows Server 2016 systems nearing end of support, across a hybrid infrastructure that includes both Hyper-V and Azure-hosted workloads.
The successful candidate will play a hands-on role in planning and executing OS upgrades while collaborating closely with infrastructure and cloud teams to ensure system stability and minimal impact to production operations.

Key Responsibilities:
OS Upgrade Execution
  • Lead and execute Windows Server 2016 upgrades across both on-prem and Azure environments
  • Plan, sequence, and deploy OS upgrades in alignment with end-of-support timelines
  • Ensure upgrades are completed with minimal disruption to business operations
Hybrid Infrastructure Support
  • Operate within a hybrid infrastructure consisting of Hyper-V and Azure servers
  • Collaborate with cross-functional teams spanning cloud and on-prem environments
  • Assess and validate system readiness prior to upgrade activities
Technical Coordination
  • Analyze existing server environments, dependencies, and configurations
  • Contribute to upgrade strategy, planning, and execution approach
  • Execute changes in a controlled manner, minimizing downtime and risk
  • Work from a defined Scope of Work (SOW), with flexibility as details are finalized

Required Skills & Experience
  • 5+ years of experience in Azure and hybrid infrastructure environments
  • Strong hands-on experience performing Windows Server OS upgrades (2016 and newer)
  • Proven experience working with Hyper-V and Azure-hosted infrastructure
  • Solid understanding of hybrid cloud architecture and operations
  • Ability to independently execute infrastructure upgrades and changes
  • Experience supporting enterprise-scale OS upgrade or remediation initiatives
  • Exposure to Azure migrations or hybrid transformation projects
  • Strong troubleshooting skills within production environments