Senior Transformation Program Director

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

Range: 162,400.00 - 243,600.00 CAD

Senior Transformation Program Director

Salary Range: $190,000 - $240,000

YOUR ROLE IN THE GAME

• Lead the end-to-end delivery of complex, multi-year business and technology transformation programs, ensuring program objectives, business outcomes, budgets, timelines, and organizational readiness are successfully achieved.
• Translate business and transformation priorities into executable programs by developing integrated roadmaps, delivery approaches, governance structures, and implementation plans that drive successful transformation outcomes.
• Personally drive program execution across multiple workstreams, bringing together business leaders, technology teams, vendors, and external partners to deliver coordinated and measurable results.
• Operate as the central point of integration across the program, proactively managing dependencies, risks, issues, decisions, and competing priorities to maintain delivery momentum and confidence.
• Lead all phases of the transformation lifecycle, from business case development, vendor selection, and planning through implementation, operational readiness, transition, and benefits realization.
• Act as a trusted delivery advisor to senior leaders and executive sponsors, translating complex program realities into clear insights, recommendations, and actionable plans.
• Prepare and lead executive governance forums and steering committees, enabling informed decision-making, transparency, accountability, and alignment across stakeholders.
• Partner closely with business and technology leaders to ensure program objectives, technology delivery, operational readiness, and implementation activities remain aligned throughout the program lifecycle.
• Manage program budgets, delivery performance, and change control activities, ensuring clear visibility into program health, value realization, and overall investment outcomes.
• Drive accountability across external partners and vendors, ensuring delivery commitments, quality expectations, contractual obligations, and program objectives are achieved.
• Establish and evolve delivery practices, governance disciplines, and performance measures that strengthen the division's capability to successfully deliver transformation initiatives.
• Foster a culture of accountability, transparency, collaboration, and continuous improvement while helping teams navigate complexity and deliver transformational change.

WHAT YOU BRING TO THE GAME

Education & Experience:

• Master's degree in Business Administration, Information Technology, Business Management, or a related discipline.
• 10+ years of progressive experience leading large-scale business and technology transformation programs with accountability for delivering strategic business outcomes.
• Experience managing the full program lifecycle, including business case development, vendor selection, governance, implementation, operational readiness, and benefits realization.
• Experience leading vendor selection, RFP, evaluation, and contracting processes for large-scale technology and transformation programs.
• Experience delivering complex technology infrastructure, software, digital, or enterprise transformation initiatives.
• Experience managing large program budgets, risks, dependencies, executive stakeholders, and cross-functional delivery teams.
• Experience establishing program management methodologies, governance frameworks, and portfolio management practices.
• Experience overseeing organizational change management, business readiness, training, communications, and transition planning activities.
• Experience working within highly regulated industries or environments with significant compliance, privacy, audit, and risk management requirements.

Relevant Skills:

• Exceptional program and transformation leadership capabilities with a demonstrated ability to lead large, complex initiatives.
• Strong executive communication, st