The Canadian Automobile Association is federation of eight Clubs providing 7 million Members with exceptional emergency roadside service, complete automotive and travel services, Member savings and comprehensive insurance services. CAA also advocates on issue of concern to its Members and all Canadians, including road safety, the environment, mobility, infrastructure, and consumer protection.
The CAA National Office supports several digital solutions including digital roadside services and a comprehensive loyalty platform that aggregates partner offers and makes them available to over 55 million CAA and AAA members across North America.
We are currently looking for a Senior Project Manager, Digital to join our CAA National team. The role is remote based within the province of Ontario.
As Senior Project Manager, you will build strong, lasting relationships with subject matter experts, clubs, and stakeholders to connect people, priorities, and ideas across the organization. This role is less about simply managing tasks and more about orchestrating outcomes—bringing together cross-functional teams across product, technology, design, and business to move important initiatives forward with clarity and momentum. You will be responsible for scope management, timelines, budgets, risks, and development sprints, while using both your technical expertise and your people skills to create alignment, build trust, and help teams do their best work. In this role, being proactive, collaborative, empathetic, and human is just as important as being organized and technically strong.
Key Responsibilities:
● Project Leadership and Delivery: Guide project scope, requirements, estimates, timelines, and priorities from planning through delivery, ensuring momentum, accountability, and clarity throughout. Manage the week-over-week priorities and RAG of key projects across the Digital team.
● Agile & Waterfall Planning and Execution: Lead backlog refinement, prioritization, and sprint planning in partnership with stakeholders and development teams to support timely, high-quality delivery. Equally comfortable working with stakeholders in a more hybrid environment supporting planning and executional cycles in a more traditional way.
● Stakeholder and Relationship Leadership: Build strong, trusted relationships with clubs, subject matter experts, and internal stakeholders to connect priorities, foster alignment, and move initiatives forward.
● Cross-Functional Orchestration: Bring together teams across product, technology, design, and business to clarify goals, coordinate efforts, and drive meaningful outcomes.
● Risk and Issue Management: Identify and communicate risks early, bring forward practical solutions working closely with the team, and help teams navigate decisions across the organization.
● Deployment & Application Support Coordination: Support the transition of solutions into production by coordinating release activities working closely with Application Support, Vendors and internal stakeholders; This includes post-launch enhancements and backlog items.
● Communication and Team Alignment: Facilitate clear communication, thoughtful documentation, and productive conversations that keep stakeholders informed, engaged, and aligned.
Education and Experience
● 6+ years of direct project management experience leading digital platforms and applications, mobile apps, custom web applications, and the supporting data, systems, and architecture behind them.
● Applicable experience working directly with client-facing groups, senior stakeholders, and cross-functional teams including product, design and development teams.
● Strong facilitation, communication, and interpersonal skills, with the ability to create clarity, alignment, and momentum across teams.
● Solid technical foundation, with a strong understanding of software development, web technologies, and digital delivery.
● Practical familiarity with Generative AI and adjacent emerging areas—such as AI agents, LLM-enabled workflows, and vibe coding—with the ability to apply these concepts in a project management context, including planning, delivery, collaboration, and process improvement.
● Deep knowledge of both Agile and Waterfall methodologies and project management best practices.
● Demonstrated ability to manage multiple priorities, navigate ambiguity, and proactively solve problems.
Assets
● Project Management diploma
● PMP
● Scrum Master (CSM)
Compensation
- $82,000 - $95,000 annual salary range
- Excellent group insurance benefits
- 3 weeks’ vacation
- Pension Plan
- Fully remote – within Ontario
This is an existing role. Employment is contingent on a successful criminal background check and references.
Apply today by submitting your resume. Deadline is June 15, 2026.
We thank all applicants for their interest; only those selected for an interview will be contacted.
We are an equal opportunity employer and are committed to an inclusive, barrier-free recruitment and selection process. CAA will provide accommodations to job applicants with disabilities through the recruitment process. If you require an accommodation, please notify us and we will work with you to meet your needs.
Pay: $82,000.00-$95,000.00 per year
Application question(s):
- How many years of direct project management experience do you have?
- Describe the most complex project you have had to deliver and what you learned from that experience?
- What is one thing about this role specifically that interested you?
Education:
- Bachelor's Degree (preferred)
Location:
Work Location: Remote
