Senior Transformation Program Director

OLG; Sault Ste. Marie; On-site; CAD 162,000 - 244,000; Full time

Benefits offered by this job

Group Benefits Plan

Public Service Pension Plan

Variable Pay Program

Paid Time Off

Growth Opportunities

Learning & Development

Equity & Inclusion

Job summary

Ontario Lottery and Gaming Corporation (OLG) in Canada is seeking an experienced Senior Transformation Program Director to lead end-to-end, multi-year business and technology transformation programs. You will align executives, vendors, and teams to deliver strategic outcomes and establish robust governance, roadmaps, and benefits realization.

You will drive execution across multiple workstreams, manage budgets and risks, and champion organizational change, ensuring readiness and measurable value

Qualifications

• Master's degree in Business Administration, Information Technology, Business Management, or related discipline.
• 10+ years leading large-scale business and technology transformation programs.
• Experience in full program lifecycle: business case, vendor selection, governance, implementation, and benefits realization.
• Experience leading vendor selection, RFP, evaluation, contracting for large-scale programs.
• Experience delivering complex technology infrastructure, software, digital, or enterprise transformations.
• Experience managing large program budgets, risks, 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.

Responsibilities

• Lead end-to-end delivery of complex, multi-year transformation programs and ensure objectives, budgets, timelines, and readiness are achieved.
• Translate priorities into executable programs by developing roadmaps, governance structures, and implementation plans.
• Drive program execution across multiple workstreams with cross-functional teams.
• Manage dependencies, risks, issues, decisions, and priorities to maintain momentum.
• Lead all phases from business case through benefits realization.
• Act as trusted delivery advisor to senior leaders and sponsors with clear insights and actionable plans.
• Prepare and lead executive governance forums and steering committees.
• Partner with business and technology leaders to keep objectives aligned throughout lifecycle.
• Manage budgets, delivery performance, and change control with visibility into value realization.
• Drive accountability across external partners and vendors.
• Establish and evolve delivery practices and governance disciplines.
• Foster accountability, transparency, collaboration, and continuous improvement.

Skills

Executive communication

Stakeholder management

Governance

Vendor management

Change leadership

Education

Master's degree in Business Administration / Information Technology / Business Management

Job description

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

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.

Range

162,400.00 - 243,600.00 CAD

Job Description

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.

Education & Experience

WHAT YOU BRING TO THE GAME

• 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, 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.

Benefits Of Joining The Winning Team

• Group Benefits Plan: Eligible employees and dependents have access to comprehensive, employer-paid group benefits coverage (permanent employees only).
• Public Service Pension Plan: Participation in a highly desirable defined benefit pension plan.
• Variable Pay Program: Participation in a performance-based incentive plan that recognizes organizational and individual achievements (permanent employees only).
• Paid Time-Off: Competitive paid time-off provisions to support work-life balance and well-being.
• Growth Focus: Become your best self with access to new opportunities and personalized support programs.
• Comprehensive Learning: 24/7 access to robust online learning programs.
• Equity, diversity, and inclusion: Core to OLG’s culture, empowering employees to bring their authentic selves and make a meaningful impact across Ontario.

To learn more about our organization and other opportunities visit our career site.

Please Note:

Unless otherwise specified, all positions are required to work fully onsite.

OLG is an equal opportunity employer. We are committed to providing employment accommodation in accordance with the Ontario Human Rights Code and the Accessibility for Ontarians with Disabilities Act. Please contact Human Resources at [e-mail] if you require accommodation at any time throughout the hire process.

We welcome applicants from all backgrounds and experiences. If you bring relevant skills and a willingness to learn, we encourage you to apply—even if you don’t meet every listed qualification.

We thank you for your interest in this opportunity; however only those individuals selected for an interview will be contacted.

Personal information is collected by the Ontario Lottery & Gaming Corporation (OLG) and/or its third party service provider(s) under the authority of the Ontario Lottery and Gaming Corporation Act, 1999, SO 1999, c 12, Sch L and the Employment Standards Act, 2000, S.O. 2000, c. 41 (as amended) and will be used for the purpose of determining qualifications for employment with OLG and for recruitment modernization initiatives. The information will be managed in accordance with all applicable laws, OLG’s Protection of Privacy Policy (the Policy) and related policies and procedures. For any questions about this collection, please contact [e-mail], 800-70 Foster Drive, Sault Ste. Marie, ON, P6A 6V2.