Sr Technology Program Delivery Manager

OLG • Toronto, ON

8d • CA$95,200 - CA$142,800 • Onsite

About The Position

We are ready to take this game to the next level and need someone passionate to lead the delivery of enterprise cybersecurity programs and initiatives that strengthen OLG’s digital resilience, reduce technology risk, and support secure business growth in a highly regulated environment. This role combines strategic program leadership, secure-by-design delivery, cyber risk management, and cross-functional partnership to ensure cybersecurity capabilities, controls, and regulatory obligations are embedded across OLG.

Requirements

• Minimum 5 to 7 years’ experience in program delivery and education, product management, within technology platforms or highly regulated environments.
• Experience in program delivery and education, product management, within technology platforms or highly regulated environments.
• Proven ability to deliver measurable program impacts in a complex, multi-stakeholder matrix organization.
• Familiarity in risk assessment methodologies, compliance issue resolution, and governance frameworks.
• Experience program delivery and marketing, including role-specific learning for diverse teams.
• Familiarity with technology-enabled solutions and digital product development processes.
• Problem Solving: Investigates complex issues to identify the root causes and impacts, assesses a range of solutions, and makes informed decisions on the best course of action, often in collaboration with other experts.
• Business Acumen: Understands OLG’s business model, financial drivers, market dynamics, and strategic priorities to support sustainable growth and risk management.
• Relationship Management: Ability to build, maintain, and strengthen productive working relationships with individuals and teams across all levels of the organization. Foster trust, collaboration, and open communication with direct reports, peers, senior leaders, and external stakeholders to drive results and support a positive work environment.
• Conflict Resolution: Ability to identify, address, and resolve disagreements or tensions within and across teams in a constructive, timely, and respectful manner to maintain a positive work environment, support collaboration, and ensure that differences do not hinder performance or morale.
• Process modelling with high level design skills: Ability to conceptualize, map, and communicate end-to-end business processes at a strategic level. It involves creating visual representations that illustrate how systems, people, and workflows interact—enabling informed decision-making, process optimization, and alignment with business goals.
• Project Management: Ability to plan, execute, monitor, and close projects effectively—balancing scope, time, cost, and quality—while leading cross-functional teams, managing risks, and aligning project outcomes with strategic business goals.
• Change Management: Ability to lead teams through organizational change by effectively communicating the vision, addressing resistance, supporting transitions, and ensuring that new processes or behaviors are adopted and sustained.
• Proficiency in Microsoft Suite (Word, Excel, PowerPoint, Teams, Planner)

Nice To Haves

• Experience in public sector gaming, with exposure to responsible / safer gambling principles, is considered an asset.
• Exposure to industry engagement, including conferences, panels, and collaboration with external partners

Responsibilities

• Lead delivery of the Cybersecurity roadmap for the enterprise information technology line of business and ensure achievement of strategic initiatives, control uplift targets, and annual OKRs.
• Embed secure-by-design practices into digital products, platforms, and initiatives by partnering with product, engineering, architecture, and operations teams from planning through implementation.
• Translate cybersecurity strategy into executable programs, business cases, delivery plans, and measurable outcomes that align with enterprise risk appetite and regulatory expectations.
• Lead cross-functional delivery of cybersecurity initiatives such as vulnerability reduction, identity and access improvements, security tooling enhancements, secure development enablement, and control remediation.
• Assess cyber risks, delivery risks, and control gaps; prioritize remediation activities; and coordinate action plans to improve security posture across the digital environment.
• Partner with governance, risk, compliance, privacy, legal, and audit stakeholders to support regulatory readiness, audit response, policy alignment, and evidence-based control management.
• Develop executive-ready reporting, dashboards, and status updates that communicate cyber program progress, risk trends, dependencies, and decision points to leadership.
• Support implementation of cybersecurity awareness and role-based enablement initiatives by ensuring training, procedures, and ways of working are integrated into operational workflows.
• Act as a primary liaison between cybersecurity, digital, and technology teams to align priorities, manage dependencies, and accelerate the adoption of security capabilities and controls.
• Use threat, incident, control, and operational insights to inform program direction, continuous improvement opportunities, and investment recommendations.
• Represent OLG in internal and external forums as required, contributing to cybersecurity governance discussions, industry collaboration, and best practice advancement.
• Serve as a delivery leader for cybersecurity initiatives in a regulated environment, balancing business enablement, resilience, compliance, and risk reduction outcomes.

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
• Education Level: No Education Listed