Lead – AI Strategic Initiatives in Toronto

We’re looking for a high-performing, strategic thinker and hands-on operator to join our Canada Operations team. This role serves as the central orchestrator for complex, cross-functional programs, ensuring successful execution from ideation through implementation and benefits realization. The successful candidate will drive project governance, planning, stakeholder alignment, and change adoption across multiple concurrent initiatives. Working closely with senior leaders, the Project Manager will ensure initiatives are delivered on time, within scope, within budget, and aligned to strategic business objectives. This role requires a strong blend of execution excellence, strategic thinking, executive communications, and change leadership to successfully navigate large-scale organizational and digital transformation efforts.

Position Responsibilities

• Transformation Delivery & Execution: Lead end-to-end delivery of strategic transformation initiatives, ensuring projects are delivered on time, within scope, budget, and quality expectations. Develop and manage integrated project plans, milestones, dependencies, and resource requirements, while driving accountability across all workstreams. Coordinate cross-functional teams, vendors, and stakeholders to resolve issues, remove obstacles, and achieve targeted business outcomes.
• Governance, Planning & Reporting: Establish and maintain project governance, ensuring effective oversight of scope, schedule, budget, risks, issues, and key decisions. Provide clear, accurate, and timely reporting on project health, progress, dependencies, and performance metrics. Partner with initiative owners to monitor benefit delivery, track progress against expected outcomes, and proactively address any realization gaps. Prepare executive presentations, steering committee materials, and leadership updates that translate complex information into actionable insights.
• Stakeholder, Risk & Financial Management: Build strong relationships with business and technology stakeholders to drive alignment, facilitate decision-making, and manage competing priorities. Proactively identify, assess, and manage project risks, issues, and cross-functional dependencies, escalating concerns with recommended actions when required. Manage project budgets, forecasts, and financial performance, ensuring strong fiscal discipline and effective benefits realization.

Required Qualifications

• 10+ years of experience in project or program management experience leading large-scale business transformation initiatives.
• Proven experience delivering complex, cross-functional programs within insurance, financial services, or other highly regulated industries.
• Demonstrated success managing project scope, schedule, budget, resources, risks, and stakeholder communications.
• Strong governance and reporting experience, including preparation of executive updates, steering committee materials, and decision papers.
• Experience managing multiple concurrent initiatives with significant organizational impact.
• Leadership experience.

When you join our team:

• We’ll empower you to learn and grow the career you want.
• We’ll recognize and support you in a flexible environment where well-being and inclusion are more than just words.
• As part of our global team, we’ll support you in shaping the future you want to see.