Director, Strategy & Business Operations - Enterprise AI

At Loblaw Digital, we know that our customers expect the best from us. Whether that means building the best, most innovative online shopping experience, or designing an app that will impact the lives of people across the country, we’re up for the challenge. From our office in Downtown Toronto, we’ve created leading eCommerce experiences in the online grocery shopping, beauty, pharmacy, and apparel spaces, and we’re only just getting started.

As the Director, Strategy & Business Operations - Enterprise AI, you will play an instrumental role on the Enterprise AI team reporting to the Senior Director, Strategic Partnerships & Innovation. You will focus on ensuring our AI efforts and investments deliver tangible, measurable value. You will help operationalize scalable understanding of the impact of our AI portfolio, and be responsible for designing, implementing, and owning the methodologies for measuring the success of our AI-led initiatives.

You will go beyond simple tracking to quantify impact across key vectors: financial return on investment, operational efficiency gains, risk mitigation, and improvements to the customer and colleague experience. Your analysis and insights will be the foundation of our strategy, providing clear, data-backed evidence that informs executive-level communications. Ultimately, your work will ensure that we are not only innovating with AI, but that we are driving tangible outcomes for the Loblaws business.

• Lead the proactive and reactive measurement and tracking of all Enterprise AI initiatives, working cross-functionally with business and finance teams to analyze performance and value.
• Develop and manage a highly organized repository of information to facilitate regular and ad-hoc reporting for senior leadership.
• Create and deliver polished, executive-level presentations and memos that provide clear, cross-functional visibility and tell a compelling story of our AI efforts and progress.
• Stay at the cutting edge of AI innovation, continuously monitoring the external landscape for emerging trends and tools.
• Translate insights from market trends and internal performance into actionable recommendations that shape our future AI strategy and identify new opportunities.

You are a strategic thinker with a strong background in business operations, corporate strategy, or financial management. You possess a unique ability to bridge the gap between complex data and clear, compelling executive narratives. Your passion for artificial intelligence is not just professional; you are deeply curious, constantly exploring the latest tools and considering their real-world applications. You thrive in a cross-functional environment and have a proven track record of delivering polished, high-stakes materials for senior executive audiences.

• 7-10 years experience in business operations, corporate strategy, cost management, or risk management.
• Exceptional communication and storytelling skills, with demonstrated ability to create and present materials for executive-level audiences.
• Exceptional financial acumen with experience in business case development, performance tracking, and ROI analysis.
• Proven ability to work collaboratively across multiple business units and functions.
• A deep and genuine passion for and understanding of the current AI landscape.
• Excellent analytical and quantitative skills.
• Ability to manage complex projects and deliver high-quality work under tight deadlines.
• Experience in the AI/ML space is an asset.

At Loblaw Digital, we seek great people to continually strengthen our culture. We believe great people model our values, are authentic, build trust and make connections.

We’re able to keep innovating because our colleagues are passionate about their work and excited about the future of eCommerce.

If you have big ideas, undeniable enthusiasm, and thrive in a collaborative, creative, and diverse group, we’ll get along just fine.

Looking for a challenge? Good. Love an innovative work environment? Even better.

Apply today.

Full time