Senior Program Director – Wealth Transformation (Insurance / Financial Services Technology) - 0153

Senior Program Director - Wealth Transformation (Insurance / Financial Services Technology) - 0153

Duration: 12 Months

Location: Toronto (Hybrid, 3x/week)

Project Name: Wealth Transformation - Dealer Integration Program

The Program Director reports to the AVP, Portfolio Management & Governance and is responsible for the strategic oversight, coordination, and delivery of complex, cross-functional technology programs that align with enterprise priorities. This role ensures that programs are delivered on time, within scope and budget, and with measurable business value. The Program Director provides leadership across multiple project teams, fosters strong stakeholder relationships, and drives governance excellence in alignment with the Technology PMO’s standards and practices.

Responsibilities:

Initiative Planning & Delivery

• Lead the end-to-end delivery of large-scale, multi-year technology programs.
• Ensure alignment with enterprise strategy, business objectives, and regulatory requirements.
• Manages and facilitates mitigation of interdependencies, risks, and resource constraints across projects.
• Evaluates program performance and recommends adjustments to scope, sequencing, or investment to maximize strategic impact.
• Champion agile and hybrid delivery methodologies where appropriate.

Stakeholder Engagement

• Build and maintain strong relationships with business and technology leaders.
• Act as a trusted advisor to executive sponsors and steering committees.
• Facilitate decision-making and issue resolution at the program level.

Governance & Reporting

• Ensure adherence to Technology PMO governance frameworks and standards.
• Provide transparent, accurate, and timely reporting on program health, risks, and benefits.
• Support audit, compliance, and risk management activities.
• Continuously improve governance processes to enhance transparency and accountability.

Team Leadership & Development

• Lead and mentor project managers and cross-functional teams.
• Foster a culture of accountability, collaboration, and continuous improvement.
• Promote knowledge sharing and best practices across the PMO.

Financial & Resource Management

• Oversees development and management of program budgets, forecasts, and resource plans.
• Ensure optimal allocation of internal and external resources.
• Track and report on financial performance and value realization

Must Haves:

• University or college degree; PMP, PgMP, or equivalent certification preferred
• Minimum of 5 years’ experience as an IT Program Manager in a Fintech, banking, insurance, or technology company managing multi-million-dollar projects
• Experience with agile frameworks (e.g., SAFe, Scrum)
• Demonstrated ability to facilitate strategic dialogue with senior executives by integrating business and technology insights to influence decisions and optimize program outcomes
• Demonstrated ability to build effective relationships with colleagues or external stakeholders to positively influence outcomes quickly and confidently
• Demonstrated ability to look at programs objectively from strategic business outcome perspective

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.