Program Director Jobs in Whitby, ON (NOW HIRING)

What you will do:

• Oversee the planning and delivery of assigned strategic initiatives; navigate ambiguity, identify risks and issues, and drive mitigation across multiple domains. 

• Lead integrated project management practices including schedule management, RAID management, dependency management, change control, and release/readiness planning. 

• Develop and maintain executive-level status reporting, dashboards, and materials that provide an integrated view of progress, decisions, risks, and outcomes. 

• Partner with stakeholders across the organization to refine the project charter, define the problem-to-solve, and translate objectives into a clear delivery approach and high-level requirements. 

• Define milestones, dependencies, assumptions, and resource needs; proactively surface trade-offs and options. 

• Establish fit-for-purpose governance and operating cadence (forums, decision logs, escalation paths), ensuring timely decisions and transparent progress. 

• Coordinate with leaders to engage the right subject matter experts and maintain role clarity and accountability across workstreams. 

• Build strong cross-functional relationships and influence outcomes through facilitation, structured problem solving, and executive-ready communication. 

• Support development of initiative-level business cases, including value drivers, costs/effort estimates, and key assumptions - tracks deployment of project budgets across multiple projects, including forecasting, variance analysis, and financial reporting. 

• Assess impacts to people, processes, and systems; ensure appropriate consideration of controls, audit practices, risk, and compliance requirements. 

• Act as a change leader by supporting stakeholder engagement, communication planning, and adoption/sustainment activities across the delivery lifecycle. 

• Contribute to annual planning by consolidating roadmaps, estimates, capacity/resource needs, and key risks across the initiative portfolio. 

• Partner with senior stakeholders to shape strategic and operational plans, ensuring initiatives remain aligned to business value and organizational strategy. 

• Drive benefits realization practices: define expected outcomes, establish baseline metrics, track delivery against targets, and support post-implementation reviews. 

• Promote continuous improvement by identifying opportunities to simplify governance, improve delivery discipline, and leverage automation and best practices. 

• Advises and coaches PMs on practical implementation of PMO practices and standards. 

What you will bring: 

• 15+ years of experience in program/project management, and/or business transformation (financial services/operations experience is an asset). 

• Post-secondary degree or equivalent combination of education and experience; PMP, PgMP, PRINCE2, Lean/Six Sigma, or Agile certification(s) are assets. 

• Demonstrated ability to lead through influence as a senior individual contributor, facilitating alignment and decisions across diverse stakeholders. 

• Strong governance and delivery discipline: scope, schedule, dependency, risk/issue, and change management. 

• Excellent communication skills with experience creating executive-ready updates, presentations, and concise written recommendations. 

• Analytical and metrics-oriented; able to define outcomes, establish baselines, and track benefits/OKRs/KPIs. 

• Agile mindset with a demonstrated ability to work through ambiguity and manage multiple time-sensitive concurrent deliverables. 

• Strong planning, organization, and attention to detail with a bias for action and follow-through. 

• Credibility to build trusted relationships across businesses and functions, provide sound advice, and challenge constructively. 

• Understanding of technology-enabled change and the impacts to operations, customers, and advisors. 

• Advanced proficiency with Office 365 applications (e.g., PowerPoint, Excel, Teams, SharePoint); experience with reporting/dashboard tools is an asset.