Executive Transformation Program Lead

olg; Toronto; On-site; CAD 190,000 - 240,000; Full time

Job summary

OLG is seeking a Senior Transformation Program Director to lead complex, multi-year programs with accountability for outcomes, budgets, and schedules. The role collaborates with business and technology leaders, vendors, and executives to ensure readiness and successful delivery across the program lifecycle.

The candidate will partner with sponsors to translate strategic priorities into actionable roadmaps and governance structures, driving measurable benefits and alignment with organizational

Qualifications

• 10+ years leading large-scale business/tech transformations.
• Experience across full program lifecycle and vendor management.
• Regulated environments with risk/compliance awareness.

Responsibilities

• Lead the end-to-end delivery of complex, multi-year transformation programs, including objectives, budgets, timelines and readiness.
• Translate priorities into executable programs with roadmaps, governance, and implementation plans.
• Drive program execution across multiple workstreams with business leaders, tech teams, vendors and partners.
• Manage dependencies, risks, issues and decisions to maintain momentum and confidence.
• Lead all phases from business case to benefits realization and transition to operations.
• Act as trusted advisor to senior leaders, translating complex realities into insights and action.

Skills

Program leadership

Transformation management

Executive communication

Stakeholder management

Education

Master's degree in Business Administration or related

Job description

OLG is seeking a Senior Transformation Program Director to lead complex, multi-year programs with accountability for outcomes, budgets, and schedules. The role collaborates with business and technology leaders, vendors, and executives to ensure readiness and successful delivery across the program lifecycle.

The candidate will partner with sponsors to translate strategic priorities into actionable roadmaps and governance structures, driving measurable benefits and alignment with organizational