Senior Program Manager

Jumbo Interactive•Calgary, AB

About The Position

Stride is a technology-enabled lottery and fundraising platform that helps charitable and non-profit organizations grow revenue through compliant, engaging, and operationally excellent gaming and fundraising programs. We work with foundations, healthcare organizations, and mission-driven partners across Canada to deliver exceptional participant experiences while maintaining strict operational and regulatory standards. Our work helps generate millions of dollars annually in support of life-changing healthcare initiatives, groundbreaking research, and essential community services across Canada. By combining strategic insight, operational excellence, and a deep commitment to our clients’ missions, we help deliver high-impact results that make a real difference in the lives of Canadians. As Stride continues to grow, we are investing further in operational excellence, cross-functional coordination, and scalable internal processes to support our next stage of expansion. We are seeking a highly organized and proactive Program Manager to support strategic initiatives, operational projects, and cross-functional execution across the organization. Position Overview This is a highly visible, client-facing role responsible for supporting the successful delivery of client programs, operational initiatives, and strategic projects across the organization. The ideal candidate is a proactive, highly organized, and solutions-oriented professional who excels at coordinating complex initiatives, improving execution, and supporting high-quality client delivery across a growing organization. This person must be comfortable managing client-facing initiatives while also helping improve internal workflows, accountability, communication, and cross-functional coordination. This is a newly evolved role designed to strengthen cross-functional execution, client delivery, and operational scalability across the organization. We are looking for someone who enjoys building operational maturity within a growing organization and can balance strategic thinking, client interaction and hands-on execution. This role reports directly to senior leadership and works closely with department leaders across the organization. The successful candidate will coordinate across established internal teams including marketing, technology, finance, operations, customer service, and compliance. This role offers significant ownership and autonomy for someone who thrives in fast-moving, growth-oriented environments.

Requirements

5+ years of experience in project management, program management, operations, client delivery, or a similar role
Proven experience supporting external clients and stakeholder relationships in a professional environment
Strong organizational mindset with demonstrated ability to improve processes and build structure
Experience coordinating complex, cross-functional initiatives involving multiple stakeholders
Exceptional organizational, communication, and follow-through skills
Ability to independently manage competing priorities in a fast-paced environment
Strong problem-solving and execution capabilities
High level of professionalism and confidence in client-facing settings
Ability to build alignment and coordinate effectively across teams

Nice To Haves

PMP certification or equivalent project/program management credentials preferred
Experience in healthcare, fundraising, gaming, SaaS, fintech, technology, or other regulated industries strongly preferred
Experience implementing or managing operational systems such as ClickUp, Asana, Monday.com, or Jira
Experience with process optimization, workflow automation, and operational reporting considered an asset

Responsibilities

Support the successful delivery of client programs, launches, and operational initiatives
Build strong and professional working relationships with client stakeholders and partners
Lead client meetings, implementation discussions, status reviews, launch planning, and issue resolution
Help manage timelines, deliverables, communication, and project coordination across client-facing initiatives
Ensure a high-quality, responsive, and professional client experience throughout all phases of engagement
Assist in translating client objectives into actionable operational plans and internal priorities
Oversee multiple concurrent projects, launches, and ongoing operational programs from planning through execution and optimization
Develop and maintain project plans, timelines, dependencies, operational trackers, and delivery schedules
Coordinate execution across marketing, technology, operations, finance, compliance, customer service, and external vendors
Help ensure priorities and deliverables remain on track across teams
Anticipate blockers, identify risks early, and proactively support solutions
Support operational readiness for launches, campaigns, and recurring program cycles
Help build and scale internal workflows, operational processes, and organizational structure
Own and maintain project management and operational workflows within ClickUp
Develop scalable templates, SOPs, dashboards, automations, reporting structures, and tracking processes
Improve organizational visibility, communication, and workflow efficiency through process improvements and operational systems
Identify inefficiencies, execution gaps, and operational risks before they impact delivery
Create structure and clarity in fast-moving or evolving environments
Support leadership in operational planning, prioritization, and organizational execution
Understand how operational decisions impact client experience, scalability, and organizational performance
Help ensure projects and programs align with company priorities and delivery objectives
Contribute ideas for process improvements, scalability, automation, and operational efficiency
Support continuous improvement initiatives across departments
Provide visibility into project status, operational performance, risks, and priorities
Prepare dashboards, operational updates, and delivery metrics
Lead operational cadence meetings and cross-functional coordination reviews
Help establish scalable project and program governance standards as the organization grows