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Senior Project Manager - Windows Server & Azure Migration

Toronto Temporary CA$80 - CA$100 per hour View Job Description
This is a unique opportunity to lead a high-profile enterprise modernization initiative involving the migration of mission-critical applications and infrastructure to modern Windows and Azure platforms at significant scale. You'll have the chance to drive strategic technology transformation, work with senior stakeholders, and leave a lasting impact on a complex environment supporting thousands of end users.

This role uses AI-assisted tools to support initial screening. All assessments and decisions are made by a human reviewer.

  • Lead a large-scale technology modernization program
  • Play a key role in shaping a complex enterprise technology landscape

About Our Client

Our client is a large, complex public-sector transportation organization undergoing significant technology modernization initiatives to support future growth, operational excellence, and digital transformation.

Job Description

  • Lead the planning, execution, and delivery of a large-scale Windows Server modernization and Azure migration program.
  • Manage project scope, schedule, budget, resources, risks, issues, and dependencies.
  • Coordinate cross-functional teams including infrastructure, application support, architecture, cybersecurity, vendors, and business stakeholders.
  • Develop and maintain project plans, status reports, executive dashboards, RAID logs, and governance materials.
  • Drive migration planning, application readiness assessments, testing, deployment, and cutover activities.
  • Ensure alignment between infrastructure, application, and business workstreams.
  • Facilitate project governance meetings, steering committees, and stakeholder communications.
  • Manage project financials, resource forecasting, and vendor deliverables.
  • Identify and mitigate project risks associated with legacy system upgrades and cloud migration activities.
  • Support change management and business readiness activities throughout the project lifecycle.



MPI does not discriminate on the basis of race, religion, sex, sexual orientation, gender identity or expression, age, disability, marital status, or based on an individual's status in any group or class otherwise protected under applicable human rights legislation. MPI encourages applications from minorities, women, the disabled and all other qualified applicants

The Successful Applicant

Required Qualifications

  • 10+ years of Project Management experience delivering enterprise technology initiatives.
  • Proven experience managing large-scale infrastructure, application modernization, or cloud migration projects.
  • Experience leading Windows Server upgrade initiatives (Windows Server 2012, 2016, 2019, or later).
  • Experience delivering projects involving Microsoft Azure environments.
  • Strong budget management and financial tracking experience.
  • Demonstrated ability to manage complex technical delivery projects involving multiple teams and stakeholders.
  • Strong understanding of software delivery and application lifecycle management.
  • Experience managing enterprise-scale environments with significant infrastructure footprints.
  • Excellent communication, stakeholder management, and executive reporting skills.



Preferred Qualifications

  • Experience within transportation, public sector, utilities, financial services, or other large enterprise environments.
  • Experience managing migrations involving 100+ servers.
  • Knowledge of Azure migration strategies, cloud infrastructure, and application modernization best practices.
  • PMP certification.
  • Experience with Agile, Waterfall, and Hybrid delivery methodologies.
  • Enterprise application migrations
  • Data centre transformation initiatives
  • Microsoft Azure cloud platforms
  • Windows Server operating system upgrades
  • Large-scale infrastructure refresh programs

What's on Offer

  • Opportunity to lead a high-profile enterprise modernization initiative involving the migration of over 100 servers and mission-critical applications to modern Windows and Azure environments.
  • Exposure to executive stakeholders and the ability to influence technology strategy, delivery approach, and modernization roadmaps.
  • Work within a large, complex enterprise environment with significant investment in cloud adoption, infrastructure transformation, and digital modernization.
  • Collaborate with experienced technology leaders, architects, infrastructure teams, and business stakeholders on a highly visible program.
  • Competitive market rate and the opportunity to make a measurable impact on a multi-year transformation initiative.
  • Contribute to technology initiatives that support critical services relied upon by millions of users every year.
Contact
Brendan Hamilton
Quote job ref
JN-062026-7030186

Job summary

Sector
Information Technology
Sub Sector
IT Project & Program Management
Industry
Public Sector
Location
Toronto
Job Type:
Temporary
Consultant name
Brendan Hamilton
Job Reference
JN-062026-7030186