Principal Product Designer, Retail

Hi there! Thanks for stopping by 👋 Are you actively looking for a new opportunity? Or just checking the market? Well… you might just be in the right place! We're looking for a Principal Product Designer — a rare, senior individual-contributor role reporting directly to the Head of Design for Retail. Lightspeed AI is our biggest bet: an intelligence layer that acts like a partner for every merchant, evolving from an assistant that answers questions into an agent that takes action. Almost nothing about designing this experience has an established playbook — how merchants delegate work to an agent, supervise it, learn to trust it, and stay in control. You'll help write that playbook. The role has two centers of gravity. First, leading design for our agentic AI experience — the defining product challenge of the next several years. Second, raising the craft bar across the entire Retail design organization: not by writing standards, but by making things — designing alongside teams in every product area to show, concretely, what great looks like. You'll also help shape our mobile point-of-sale strategy as a secondary focus. This is not a management role. It's for a maker who moves fluidly between defining strategy and pushing pixels — someone who can hold the full context of a large product portfolio and still be the strongest hands-on designer in the room. Location: Toronto preferred; open to other locations in Ontario, Quebec and Eastern Canada. What you'll be doing: - Define new interaction patterns for agentic AI — designing how merchants converse with, direct, supervise, and build trust in an intelligent agent that works on their behalf. - Lead design for our AI experience end-to-end as a hands-on IC: from concept and prototype through polished, shipped product, in close partnership with AI engineering and product leadership. - Raise the craft bar across the organization through direct contribution — jumping into any product area to explore, elevate, and unblock the most important work, and leaving teams stronger than you found them. - Lead vision work that rethinks core merchant experiences through hands-on exploration and prototyping — concept work ambitious enough to shape strategy and concrete enough to build. - Prototype with AI, daily: work AI-first — using modern tools to move from intent to working prototype fast — and model this way of working for designers across the org. - Shape our mobile strategy with design thinking and hands-on support, as an ongoing secondary focus. - Influence without authority: align designers, leaders, and cross-functional partners across multiple teams through clarity, storytelling, and the quality of the work itself. What you need to bring: - 12+ years of product design experience with a maker's mindset — moving fluidly between strategic thinking and detailed, polished execution. - A portfolio demonstrating exceptional hands-on craft across UX, interaction, and visual design — work that other designers point to. - Experience leading large, ambiguous initiatives across multiple teams and delivering measurable outcomes — without formal authority. - Genuine fluency with AI: active use of LLMs and AI prototyping tools in your workflow, and a strong point of view on designing AI-powered products. - Enough technical understanding to be a real partner to engineers — you can build prototypes to communicate ideas and reason about constraints. - The ability to influence senior stakeholders through clear communication, storytelling, and tangible design work. - Taste. You know what great looks and feels like, and you push — and help others push — to get there. We know that people are more than what's on their CV. If you're unsure that you have the right profile for the role… hit the 'Apply' button and give it a try! Be a changemaker You’ll enjoy: - A flexible work environment that empowers you to do your best work - A culture that celebrates performance - The chance to make an impact in a team that’s…