Senior Manager, Project Management & Operations

Senior Manager, Project Management & Operations

About Stride

Stride is a full-service lottery and fundraising organization that helps charitable and non-profit organizations generate revenue through professionally managed lottery programs across Canada.

For more than 30 years, Stride has brought together the strategy, marketing, technology, customer service, finance, operations, regulatory expertise, and project management required to plan, launch, and operate successful lottery campaigns. We work with foundations, healthcare organizations, and other mission-driven organizations to generate significant funding for healthcare initiatives, research, and community services.

Position Overview

The Senior Manager, Project Management & Operations is accountable for the successful delivery of Stride’s lottery campaigns.

This is a senior, hands-on role responsible for turning campaign plans into execution. The Senior Manager oversees the many moving parts required to plan, launch, operate, and close out campaigns, ensuring that internal teams deliver what is required, when it is required, and to the expected standard. The role will also directly lead selected campaigns and projects.

The position is highly client-facing, with responsibility for managing the client relationship from a project delivery perspective. This includes keeping clients informed, managing timelines and approvals, providing revenue and budget updates, resolving issues, and ensuring commitments are delivered as agreed.

The Senior Manager also oversees Stride’s project management function and provides leadership to the project management team, ensuring consistent and effective project management practices across the organization.

Key Responsibilities

Lottery Campaign Operations & Delivery

• Own the end-to-end delivery of assigned lottery campaigns from initial planning and preparation through launch, live campaign operations, and post-campaign close-out.

• Personally lead selected campaigns and projects, taking ownership of the overall delivery plan and outcomes.

• Develop and maintain detailed project plans, Gantt charts, timelines, milestones, dependencies, critical paths, and key deliverables.

• Bring together the internal teams and external partners required to deliver each campaign and ensure responsibilities, handoffs, and deadlines are clearly understood.

• Monitor execution closely and proactively address issues, risks, dependencies, and changes that could affect delivery.

• Ensure all internal campaign requirements are completed and campaigns are fully prepared for launch.

• Maintain oversight throughout the live campaign period, ensuring issues are identified and resolved quickly and execution remains coordinated.

• Lead post-campaign activities, including reporting, reconciliation, outstanding deliverables, and close-out.

• Identify practical opportunities to improve campaign workflows, execution, efficiency, and scalability.

Client & Project Delivery

• Own the day-to-day client relationship for assigned campaigns from a project delivery perspective.

• Lead regular client status meetings and provide clear updates on campaign progress, timelines, deliverables, approvals, revenue, budgets, risks, and issues.

• Develop effective working relationships with client stakeholders and ensure project communications, expectations, and commitments are appropriately managed.

• Coordinate client inputs, decisions, and approvals required to keep campaigns moving and on schedule.

• Ensure client commitments are reflected in internal execution and delivered as agreed.

• Act as the central point of contact for project-related questions, issues, and changes, resolving matters effectively and escalating when appropriate.

Project Management Leadership

• Oversee Stride’s project management function, including the project management team, project management tools, and consistent application of project practices.

• Lead, coach, and support project management team members in the effective delivery of their work.

• Establish and maintain practical approaches to project planning, tracking, reporting, risk management, and project governance.

• Ensure effective use of ClickUp and other project management tools to provide visibility into project status, deliverables, and accountability.

• Identify and implement improvements to project management practices and cross-functional workflows within established organizational and regulatory requirements.

Qualifications

• 8+ years of progressive experience in project management, program management, operations, client delivery, or a related discipline.

• PMP or equivalent project management certification

• Proven experience leading complex, cross-functional projects from planning through completion, preferably in a client-facing environment.

• Strong experience developing and managing detailed project plans, timelines, dependencies, milestones, budgets, and project reporting.

• Demonstrated ability to manage client relationships and communicate effectively with senior client stakeholders.

• Strong operational orientation with the ability to understand the detail, identify what needs to happen, and drive execution across multiple teams.

• Excellent organization, attention to detail, judgment, communication, and follow-through.

• Strong problem-solving skills and the ability to anticipate issues, manage competing priorities, and make sound decisions.

• Experience leading or mentoring project management resources.

• Demonstrated ability to improve processes and ways of working within established organizational and regulatory requirements.

• Strong business acumen, including an understanding of the relationship between project execution, client experience, revenue, cost, and risk.

• Experience with ClickUp or a comparable project management platform.

• Experience in lottery, fundraising, healthcare, or another complex or regulated environment is an asset