Senior Project Manager – Software Implementation (AI)

Location: Toronto, Ontario, Canada; flexibility to work in-office, virtually, or in a combination of both.

Salary: $85,000–$110,000 per year.

Company

Health and well-being technology provider delivering solutions for physical, mental, and financial health, including retirement and benefits platforms.

What you will do

• Lead end-to-end software implementation delivery from initial client engagement through go-live and transition to operations.
• Manage scope, schedule, budget, quality, financial tracking, change control, and resource allocation across multiple workstreams.
• Lead governance forums, steering committees, executive reviews, and decision meetings with senior client stakeholders.
• Coordinate configuration, data, QA, product, development, and integration teams.
• Identify and manage risks, dependencies, timeline scenarios, and delivery trade-offs before they become critical issues.
• Improve PMO practices, mentor project managers and coordinators, and apply AI and automation to dashboards, risk analysis, dependency mapping, and forecasting.

Requirements

• 5+ years of project management experience delivering complex Defined Benefit pension implementation projects end-to-end.
• Strong experience with client-facing software implementation involving multiple workstreams and senior stakeholders.
• Deep knowledge of pension administration processes, challenges, and technology landscapes.
• Executive-level communication, stakeholder management, governance, risk management, financial control, and change control skills.
• Experience leading integrated multidisciplinary teams across configuration, data, QA, product, development, and integration.
• Hands-on experience with generative AI, copilots, or automation, including responsible use of enterprise tools, data privacy, and security.

Nice to have

• Bilingual proficiency in English and French.
• PMP or similar project management certification.
• Experience with SaaS platforms, data migration, and system integrations.
• Familiarity with Azure DevOps, Jira, or comparable tools.

Culture & Benefits

• Competitive salary and bonus structures with a comprehensive total rewards package.
• Minimum three weeks of vacation and a flexible benefits plan.
• Company-matched pension.
• Career growth and learning and development opportunities.
• Inclusive, customer-first culture focused on innovation, continuous improvement, mentorship, and responsible use of AI.