Principal Project Manager - Microsoft Jobs, Toronto

AI Summary

Microsoft Canada is seeking a Principal Project Manager in Toronto, ON. This role leads complex digital and AI transformation programs, driving significant business outcomes for customers. Key duties involve owning end-to-end program accountability and serving as a strategic advisor. Top requirements include 7+ years of project management experience and leading large-scale enterprise transformation initiatives.

About the Principal Project Manager Role at Microsoft Canada

As Microsoft enters a new era, the Principal Project Manager plays a pivotal role in enabling faster, AI-powered business outcomes for our customers across Canada. This position is central to Microsoft's commitment to delivering complex digital and AI transformation programs. Operating at the intersection of customer transformation, delivery excellence, and business growth, this leader helps our largest customers realize value from multi-million-dollar transformation programs. The successful candidate will lead some of Microsoft's most strategic customer engagements, driving business outcomes across large, complex projects that span multiple workstreams, technologies, partners, and stakeholder groups. This is a critical leadership position, not a project coordination role, where the Principal Project Manager acts as a trusted advisor to customer executives, influencing decision-making and orchestrating diverse Microsoft teams across sales, engineering, architecture, customer success, and delivery organizations to achieve desired outcomes. The focus is always on accelerating growth, improving productivity, optimizing operations, and unlocking new sources of value through Microsoft Cloud and AI.

Driving Customer Transformation and Program Leadership

The Principal Project Manager holds end-to-end accountability for complex enterprise transformation programs, aligning technology investments directly to measurable customer business outcomes. This involves serving as a strategic advisor to customer executives and transformation leaders, driving outcome realization, adoption, organizational readiness, and value measurement throughout the engagement lifecycle. From vision and ideation through implementation, adoption, and scale, this role ensures successful project delivery. Program leadership and execution are paramount, establishing robust governance structures, operating rhythms, and executive reviews. The Principal Project Manager leads program planning, mobilization, execution, risk management, and dependency management, translating complex business objectives into actionable workstreams and measurable outcomes. Effective executive stakeholder management is also key, building trusted relationships across customer executive teams, Microsoft leadership, and partner organizations, and communicating program health with clarity and transparency. This individual acts as the voice of the customer within Microsoft and the voice of Microsoft with the customer, ensuring a seamless experience.

Qualifications and AI-First Delivery

Candidates for this Principal Project Manager position must possess a Bachelor's Degree in a related field and at least seven years of experience in project management, or equivalent experience. Preferred qualifications include significant experience leading large-scale enterprise transformation programs and managing complex, cross-functional initiatives involving business, technical, and executive stakeholders. Strong executive communication and stakeholder engagement skills are essential, alongside demonstrated experience managing program financials, risk, governance, and delivery outcomes. Experience leading teams and influencing across matrixed organizations, particularly within Consulting, Technology Services, Systems Integration, or Digital Transformation organizations, is highly valued. A key aspect of this role is championing AI-first thinking in customer engagements and internal operations. The Principal Project Manager will help customers identify, prioritize, and accelerate high-value AI use cases, leveraging AI capabilities to improve delivery predictability, productivity, governance, and overall business outcomes. This includes leading projects involving Copilot, Azure AI, Data & Analytics, Fabric, Security, and other emerging Microsoft technologies, ensuring a cutting-edge experience for our customers.