Program Director, Real Estate

Work Arrangement: Hybrid - minimum 3 days onsite per weekRole OverviewWe are seeking a highly strategic and execution-focused Senior Program Lead to oversee multiple large-scale real estate transformation programs within a complex corporate environment.
The successful candidate will have extensive experience managing enterprise-level programs, coordinating multiple Project Managers, overseeing large budgets, and engaging senior executive stakeholders.
Direct corporate real estate experience is mandatory.
Experience in wealth management, investment management, or financial services is strongly preferred.
This role requires a hands-on leader who can drive execution, manage competing priorities, identify risks, and ensure strategic initiatives are delivered on time, within budget, and within scope.
Key Responsibilities
Program & PMO Leadership:
Oversee multiple concurrent programs and workstreams while coordinating and mentoring a team of 6 Project Managers.
Real Estate Transformation:
Lead complex real estate initiatives, including office consolidation, workplace transformation, and real estate portfolio optimization.
Program Execution:
Manage project plans, milestones, dependencies, budgets, deliverables, and resource priorities across multiple initiatives.
Executive Governance:
Prepare executive-level reports, recommendations, presentations, and updates for steering committees and senior leadership.
Financial & Risk Management:
Monitor program budgets, identify risks and issues, develop mitigation plans, and drive timely resolution.
Stakeholder Management:
Build alignment across business leaders, internal teams, and external delivery partners.
Performance Reporting:
Use dashboards, KPIs, and reporting frameworks to track progress, highlight issues, and support data-driven decisions.
Change & Quality Management:
Manage scope changes, maintain delivery standards, and ensure adherence to established project management frameworks.
Continuous Improvement:
Identify opportunities to improve delivery processes and implement lessons learned across programs.
Required Qualifications
10+ years of experience leading complex, cross-functional projects or enterprise programs.
Mandatory experience in corporate real estate, workplace transformation, capital projects, or real estate portfolio optimization.
Demonstrated experience managing PMOs, multiple concurrent programs, and several Project Managers.
Strong financial management, budgeting, risk management, and governance experience.
Proven ability to influence senior executives and manage stakeholders across complex organizations.
Exceptional strategic thinking, analytical, organizational, and problem-solving skills.
Strong written and verbal communication skills, including executive-level reporting and presentations.
Ability to prioritize competing demands and drive results without direct people-management authority.
University degree or college diploma in Business, Project Management, Real Estate, Construction Management, or a related field.
PMP, PgMP, PRINCE2, or equivalent certification is preferred.
Preferred Qualifications
Experience in wealth management, investment management, banking, or financial services.
Experience overseeing large-scale real estate programs with significant budgets and multiple workstreams.
Additional Requirements
Must be based in or able to work onsite in Toronto or Winnipeg.
Minimum of 3 days onsite per week.
Must be available for a 1-year contract.
Direct real estate experience is mandatory. Candidates should demonstrate senior-level program leadership, strong PMO coordination, and experience delivering complex initiatives in a corporate environment.
AI in Recruitment NoticeAI-enabled tools may be used to assist with aspects of the recruitment and candidate screening process. All hiring decisions are made by human decision-makers.
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