Senior Transformation Program Director

OLG • Toronto, ON

2d • CA$162,400 - CA$243,600 • Onsite

About The Position

We are ready to take the game to the next level and are seeking an experienced transformation leader to lead the delivery of complex business and technology transformation programs that will shape the future of the Lottery business. This role will lead complex, multi-year initiatives that enable new capabilities, support evolving customer experiences, and deliver strategic business outcomes. As Senior Transformation Program Director, you will serve as the senior delivery leader for large-scale transformation programs, providing delivery leadership, strategic guidance, and enterprise-wide coordination from concept through implementation and value realization. You will align business leaders, technology teams, external partners, and executive stakeholders to successfully deliver transformational outcomes while establishing the delivery disciplines, governance practices, and capabilities that support future transformation initiatives.

Requirements

• 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.
• Exceptional program and transformation leadership capabilities with a demonstrated ability to lead large, complex initiatives.
• Strong executive communication, stakeholder management, influencing, negotiation, and relationship-building skills.
• Expertise in program governance, portfolio management, risk management, organizational change leadership, and benefits realization.
• Strong analytical, problem-solving, prioritization, and decision-making capabilities.
• Ability to translate complex business and technology challenges into clear delivery plans, executive communications, and actionable outcomes.
• Proven ability to build alignment and drive accountability across diverse stakeholder groups, executive sponsors, vendors, and delivery teams.
• Strong financial acumen with experience managing program budgets, business cases, investment governance, ROI measurement, and value realization.

Responsibilities

• 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.

Benefits

• Eligible employees and dependents have access to comprehensive, employer-paid group benefits coverage (permanent employees only).
• Participation in a highly desirable defined benefit pension plan.
• Participation in a performance-based incentive plan that recognizes organizational and individual achievements (permanent employees only).
• Competitive paid time-off provisions to support work-life balance and well-being.
• Become your best self with access to new opportunities and personalized support programs.
• 24/7 access to robust online learning programs.
• Core to OLG’s culture, empowering employees to bring their authentic selves and make a meaningful impact across Ontario.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior