Program Director

Program Director
12 Month Contract
Toronto or Winnipeg, 3 days on site

The Role 
We are seeking a highly experienced, execution-focused Program Lead who thrives in complex environments and is accountable for delivering strategic outcomes. This is a hands-on functional leadership role requiring active coordination of multiple high-priority workstreams, executive stakeholders, and external partners to successfully deliver critical real estate transformation initiatives.

Key responsibilities: 
Project Management Team – 6 Project Managers
The role provides day-to-day mentorship, point of escalation, coordination, prioritization, and workflow direction to assigned project managers; however, it has no people leadership, performance management, hiring, compensation, or talent management responsibilities.
Program Orchestration & Multi-Workstream Management
Concurrently manage three strategic real estate programs, across varying phases of execution – approximately 40 in-flight projects for 2027, with an annual spend of $45M; and, 25 in 2028 with a $33M spend. Maintain a single source of truth — tracking milestones, dependencies, owners, and blockers in real time. Proactively surface misalignments before they become issues, and keep all moving parts visible and accountable.
Project Planning and Execution
Collaborate with stakeholders to define project objectives, scope, deliverables, and success criteria aligned with business goals. Take an active, hands-on role in execution — directly contributing to problem-solving, solution development, and driving progress, not just overseeing it.
Support executive governance forums, steering committees, and decision-making processes through the preparation of executive-ready reporting, recommendations, and briefing materials. Attend Distribution Governance Committee and Toronto Project Leadership Committee.
Analytical Decision-Making
Leverage data, dashboards, and KPIs to inform decision-making, track program performance, and demonstrate measurable impact. Build and maintain reporting frameworks that translate operational data into clear, executive-ready insights. Identify trends, anomalies, and risks before they surface in outcomes. Partner closely with Strategy, Planning & Execution as a consumer of their analytic & reporting services.
Prioritization Under Pressure
Rapidly re-prioritize workloads as business needs shift. Make transparent trade-off decisions, communicate changes proactively to stakeholders, and ensure the team stays focused on the highest-impact work at all times.
Initiation and Ownership
Proactively identify gaps, risks, and opportunities. Take personal accountability for following through on action items and driving resolution — even in the face of ambiguity. Champion a culture of high-quality outcomes across yourself and the team.
Risk & Issue Management
Identify, assess, and anticipate risks as projects evolve in a dynamic environment. Develop robust mitigation and contingency plans. Take ownership of driving resolution, not just escalation.
Cross-Functional Collaboration
Build strong partnerships across functions. Navigate complex organizational structures, foster open communication, and align diverse stakeholders to deliver cohesive outcomes. Lead updates and collaborate with the business leads for IGWM Distribution Real Estate.
Communication & Reporting
Communicate project status, risks, and solutions clearly and concisely (written & verbally) — both upward to senior executives and across teams. Tailor communication style to audience needs. Provide accurate, timely updates that enable confident decision-making at all levels.
Quality & Change Management
Ensure all deliverables meet quality standards through hands-on involvement and thorough review. Proactively manage changes to scope, schedule, and resources through structured change control processes. Lead Project Managers to execute against the Delivery Framework; as a consumer of the framework, collaborate with Practise Management on opportunities to refine and improve processes.
Process Improvement & Lessons Learned
Lead post-project reviews to capture insights and best practices. Continuously seek and implement improvements to how the team operates.
Qualifications & Experience
Education
University degree or college diploma in Business, Project Management, Real Estate, Construction Management, or a related discipline. PMP, PgMP, PRINCE2, Lean, or equivalent project/program management certification preferred.
Experience
Progressive experience in corporate real estate, workplace transformation, capital projects, portfolio optimization, or related disciplines, including at least 10 years leading complex cross-functional projects or programs.
Personal Attributes

• Exceptional program and project management capabilities.
• Strong strategic thinking and execution orientation.
• Advanced stakeholder management and influencing skills.
• Superior organizational and prioritization abilities.
• Strong analytical and problem-solving skills.
• Ability to operate effectively in ambiguous and rapidly changing environments.
• Advanced executive communication and presentation skills.
• Strong financial, risk management, and governance acumen.
• Demonstrated ability to drive accountability and results without direct authority.
• High degree of personal ownership, initiative, and accountability.

Success Measures

• Delivery of assigned strategic programs within approved scope, budget, and schedule.
• Effective management of program risks, dependencies, and stakeholder expectations.
• Timely and accurate executive reporting and governance support.
• Achievement of defined program outcomes and transition objectives.
• Successful coordination of internal teams and external delivery partners.