Senor Project Manager - Enterprise Digital Transormation

Location: Toronto/London

8 month Contract

The Senior Project Manager plays a critical role in leading large, high-risk, multi-workstream digital transformation projects with significant business impact, within the Technology PMO, delivering innovative solutions that modernize insurance benefits and operations while elevating client experience. This role combines strategic project leadership, stakeholder engagement, and change management to drive impactful outcomes across enterprise platforms and emerging technologies.

Working on the front line with our business partners, vendors, and other stakeholders, this role is highly visible and collaborative to deliver initiatives on time and within budget. It is a professional role that combines strong Project Management, Business Relationship, and Change Management skills to drive strategic outcomes and transformation. This role reports to the Manager, Project Delivery, within the Workplace Benefits & Retirement, Digital, AI, Applications and Platforms, and Canadian Operations & Business Enablement portfolio.

• Accountable for end-to-end delivery of complex digital initiatives, driving innovation and transformation while ensuring alignment with PDLC, governance standards, and organizational objectives.
• Accountable for delivering business outcomes and ensuring alignment with organizational objectives.
• Partner with senior and executive stakeholders to influence decisions and manage trade-offs.
• Lead cross-functional teams through ambiguity and drives organizational change.
• Develop comprehensive project plans for large, complex initiatives with multiple workstreams, ensuring alignment with business objectives and governance standards, in partnership with internal and external stakeholders and work with third-party vendors to integrate plans and align deliverables.
• Manage overall project governance including stakeholder communication, meeting facilitation, documentation, resources, financials, scheduling, and status reporting.
• Perform qualitative and quantitative risk analysis and manages complex budgets and forecasts.
• Develop detailed project plans, stakeholder matrix, RAID logs, cut-over plans, and financial summaries and executive steering presentations and dashboards, as required.
• Coordinates internal and external resources and monitors deliverables.
• Monitor and track projects in internal systems; monitors resource usage vs. budget and prepares and updates cost plans regularly.
• Work proactively to resolve issues and mitigate risks.
• Adjust plans and communication to achieve desired outcomes.
• Ensure project documentation is complete and current.
• Conduct post-implementation reviews and documents lessons learned.
• Build and foster productive relationships with stakeholders.
• Collaborate with security, risk, and compliance teams for required assessments and artefacts and manages all technical project risks, ensuring compliance with established cyber and risk controls.
• Champion continuous improvement initiatives and participates in internal community of practice project management events and development opportunities.
• Mentor project managers and team members on processes and tools.
• Other duties as assigned.

Must Haves:

• Minimum 5 to 10 years of experience managing large complex projects with multiple workstreams, including digital transformation initiatives, software implementations, integrations, and data migration.
• PMP or equivalent certification required; Agile/SAFe certifications considered an asset.
• Proven ability to lead large, complex projects in a fast-paced, dynamic environment.
• Proven ability to influence senior leadership and manage executive-level stakeholders, including communications and negotiations.
• Strong track record of stakeholder management and leading cross-functional teams to achieve project deliverables.
• Ability to lead through ambiguity, drive organizational change and simplify complex situations to deliver results under tight deadlines.
• Deep understanding of Project Delivery Life Cycle (PDLC) and governance frameworks.
• Experience with digital platforms, AI, cloud technologies, and data-driven solutions considered an asset.

NICE TO HAVES

• Experience mentoring project managers and fostering high-performing teams.
• Experience delivering projects with enterprise-level impact.
• Relevant credentials such as PMI-PBA, Agile Certified Practitioner (PMI-ACP), Certified ScrumMaster (CSM), or SAFe Agilist considered an asset.
• Advanced knowledge of project management methodologies (Agile, Waterfall, Iterative) and tools (MS Project, JIRA, Confluence, SharePoint).
• Bilingualism (English/French) is an asset.