Program Manager AI Activation – Canadian Tire – Toronto, ON
Location: Toronto, ON | Company: Canadian Tire
Canadian Tire Corporation is one of Canada’s most recognized and trusted retailers, and they’re looking for a strategic Program Manager, AI Activation to join their growing team in Toronto, Ontario. This is a senior-level opportunity to lead the end-to-end orchestration of AI initiatives at the portfolio level, working directly under the AVP of AI Activation.
This role sits at the intersection of AI strategy and program execution, giving you ownership over how complex, multi-project AI programs are structured, governed, and delivered across Canadian Tire’s enterprise. If you thrive on building delivery standards, leading project managers, and engaging with senior stakeholders, this position offers real scope and visibility.
About the Role: Program Manager, AI Activation
As the Program Manager, AI Activation, you’ll own the AI Activation program portfolio end-to-end — from translating high-level AI strategy into structured programs down to the individual project level. You’ll be accountable for consistent program design, dependency management, sequencing, and ensuring all initiatives deliver measurable business outcomes. This role also means directly leading, coaching, and supervising all AI Activation Project Managers, holding them to clear delivery standards across planning, milestones, RAID management, and status reporting.
Beyond day-to-day delivery, you’ll own program-level governance, including cost-benefit analyses, financial forecasting, and executive readiness. You’ll partner with Finance, PMO, and business leadership to maintain funding transparency and ensure AI initiatives meet enterprise audit and governance expectations. Cross-functional relationship building is central to this role, as you’ll serve as the primary program interface with senior stakeholders across IT, Finance, Data, and Business teams.
Benefits and Salary
Canadian Tire offers a broadband salary range of $79,000 to $131,000, with final compensation determined based on experience, internal equity, and market conditions. Beyond competitive pay, employees receive comprehensive benefits and retirement programs, performance incentives, continuing education programs, mental health benefits of $5,000 per year for eligible employees and their families, career growth opportunities, product discounts, Canadian Tire Profit Sharing, and Triangle Learning Academy access.
Job Details
📌 Job Type: Full-Time
🏢 Company: Canadian Tire Corporation
📍 Location: Toronto, ON
🆔 Requisition ID: JR160416
💰 Pay: $79,000 – $131,000 per year
Responsibilities
This role demands a blend of strategic thinking and hands-on delivery leadership. As the single point of accountability for the AI Activation program portfolio, you’ll be shaping how AI work gets done across the enterprise — while also rolling up your sleeves to unblock teams and drive execution forward.
- Own the AI Activation program portfolio, structuring work from the Big Rock level down through programs and individual projects
- Lead, coach, and supervise all AI Activation Project Managers, setting consistent delivery standards across planning, milestones, and RAID management
- Intervene proactively when delivery is off-track, unblocking PMs and escalating issues where required
- Manage program-level governance, including CBAs, financial forecasting, tracking, and executive readiness
- Partner with Finance, PMO, and leadership to ensure funding, benefits realization, and financial transparency across all AI initiatives
- Own and standardize Planview and portfolio tooling for AI Activation, defining program and project structures, documentation standards, and SharePoint artifact organization
- Act as the primary program interface with senior stakeholders across IT, Finance, Data, and Business, preparing executive-ready updates and decision framing
- Ensure all AI initiatives meet enterprise governance and audit expectations
Requirements / Skills
The ideal candidate brings deep experience in program and portfolio management within complex, cross-functional technology environments. Canadian Tire is looking for someone who can confidently operate between strategy and hands-on execution, and who has a track record of leading project managers directly — not just managing individual projects.
- Proven experience leading programs of multiple projects, with accountability at the program or portfolio level
- Strong background in financial governance, including cost-benefit analysis, forecasting, and benefits realization tracking
- Experience delivering complex, cross-functional technology or AI programs within a large enterprise setting
- Demonstrated ability to lead and coach PMs directly, including performance management responsibilities
- Comfortable bridging strategy and execution, translating high-level direction into structured, well-governed delivery plans
- Familiarity with portfolio management tools such as Planview, and proficiency with documentation and artifact management practices
How to Apply
To apply, visit the official job posting using the link below. Make sure your resume is up to date and tailored to the program management and AI delivery experience outlined in this posting before submitting.
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Job Summary & Tips for Applying
Quick Summary & What to Highlight: This Program Manager, AI Activation role at Canadian Tire in Toronto is perfect for candidates who excel in program portfolio management, financial governance, and cross-functional stakeholder engagement. On your resume, emphasize any experience with AI or technology program delivery, direct supervision of project managers, and your ability to work in a fast-paced, enterprise environment. If you’ve previously worked in technology program management or AI/data delivery roles, make sure to highlight specific achievements and responsibilities that align with this position.
Resume & Application Tips: Before applying, tailor your resume to match the job description. Include keywords like program portfolio management, AI Activation, and financial governance that appear in the posting. Quantify your achievements where possible (e.g., “managed a portfolio of 8 concurrent AI projects valued at $5M” or “led a team of 6 project managers across 3 business units”). Write a brief cover letter expressing your genuine interest in Canadian Tire and why you’re a strong fit for this program leadership role in Toronto. Double-check your application for spelling errors and ensure your contact information is current.
Interview Preparation: If selected for an interview, research Canadian Tire‘s values, AI strategy, and recent innovation initiatives beforehand. Prepare specific examples using the STAR method (Situation, Task, Action, Result) to demonstrate your program leadership and governance experience. Common questions may include scenarios about managing delivery risk, coaching underperforming project managers, and presenting program status to executive stakeholders. Dress appropriately for a corporate technology environment, arrive 10-15 minutes early, and bring copies of your resume. Prepare thoughtful questions about the AI Activation portfolio, team structure, and growth opportunities. After the interview, send a thank-you email within 24 hours reiterating your interest in the position.