Sr. IT Project Manager (Agile) with experience leading digital transformation projects within the financial services domain - 7294 & 5718

Duration: 10 Months

Location: Toronto, London or Winnipeg (Hybrid, 3x/week onsite)

• Lead large, high-risk, and complex projects or programs (often multi-workstream) to deliver defined business outcomes and organizational value.
• Lead digital transformation initiatives including software implementations, integrations, and data migrations across enterprise platforms.
• Partner with senior and executive stakeholders to define scope, develop project charters, and align objectives with business and technology strategies.
• Influence decision-making, manage trade-offs, and provide clear executive-level communications and reporting.
• Build comprehensive project plans including budgets, timelines, resource strategies, RAID logs, and delivery approaches.
• Apply strong technical, business, and financial acumen to ensure deliverables support strategic priorities and client needs.
• Provide leadership to cross-functional and multi-disciplinary teams, offering coaching and mentorship to drive performance and collaboration.
• Integrate and adapt delivery methodologies (Agile, Waterfall, Iterative, Hybrid) based on project and regulatory requirements.
• Manage complex stakeholder and vendor relationships, facilitating communication, negotiations, and issue resolution.
• Oversee end-to-end project execution aligned to PDLC and governance frameworks, ensuring risks are mitigated and compliance standards are met.
• Manage project governance including financial tracking, scheduling, resource forecasting, and status reporting.
• Coordinate internal teams and third-party vendors to ensure integrated delivery plans and aligned outcomes.
• Ensure operational readiness, change management, and smooth transition to business operations.
• Conduct post-implementation reviews and capture lessons learned.
• Drive continuous improvement and promote PMO best practices and standards.

• 5-10 years managing medium to large, complex projects/programs across varying methodologies and levels of ambiguity.
• Proven experience delivering digital transformation initiatives in financial services environments.
• University/College education in Project Management, Business Administration, or related field (or equivalent experience).
• PMP (preferred) or Prince2 certification; Agile/SAFe certifications are assets.
• Deep knowledge of project management methodologies and ability to tailor them to complex initiatives.
• Strong experience managing senior/executive stakeholders and cross-functional teams.
• Demonstrated ability to influence leadership and drive decisions.
• Strong business, technical, and financial acumen.
• Experience with governance frameworks and Project Delivery Life Cycle (PDLC).
• Strong experience with PM tools: MS Project, JIRA, Confluence, SharePoint.
• Strong knowledge of Agile, Iterative, and Waterfall methodologies.
• Demonstrated expertise in risk assessment, mitigation, and financial management.
• Experience using Book of Record systems for project tracking and reporting.
• Excellent communication and presentation skills, including translating technical concepts for business audiences.
• Ability to lead through ambiguity and drive organizational change.

• Experience in insurance, benefits, or retirement services domains.
• Exposure to digital platforms, AI, cloud, or data-driven solutions.
• Experience managing enterprise-level or multi-workstream programs.
• Vendor and third-party delivery management experience.
• Mentoring junior PMs or contributing to PMO communities of practice.
• Bilingual (English/French).
•