Head of Product Design, Retail
Job in
Toronto, Ontario, M5A, Canada
Listing for:
Lightspeed
Full Time
position
Listed on 2026-02-15
Job specializations:
-
Design & Architecture
Product Designer, Digital Media / Production
Job Description & How to Apply Below
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Lightspeed Retail is seeking an experienced and visionary Head of Design to lead our product design organization. This pivotal role will be responsible for defining and executing the design strategy across our entire suite of retail products, ensuring a cohesive, intuitive, and delightful user experience. You will build, mentor, and inspire a world-class team of product designers, fostering a culture of innovation, collaboration, and user-centricity.
This role requires a strategic thinker with a strong design-thinking background, capable of translating complex business needs into elegant and impactful design solutions.
As our Head of Product Design for Retail
, you'll be instrumental in shaping the entire Lightspeed Retail experience ecosystem
, encompassing Wholesale, In-store Selling, and Online channels. Your leadership will ensure a cohesive, seamless, and highly competitive experience that directly impacts merchants in the real world, empowering them to build thriving businesses. You'll set the strategic design vision for our Retail products and be accountable for your team's collective performance and delivery.
Eligible candidates must be based in eastern Canada or the United States.
What you’ll be doing:
Global Design Leadership & Vision: Lead, mentor, and empower a diverse team of product designers across North America, EMEA, and APAC. Define and champion the overall design vision and strategy for Lightspeed Retail products, ensuring alignment with business objectives and user needs across our entire product portfolio, including those with AI-driven features.Empowering Autonomous Teams: Foster an environment where designers embedded in highly autonomous product teams ("squads") can collaborate effectively through both synchronous and asynchronous methods, driving design quality and efficiency.User Experience Excellence: Oversee the end-to-end design process, from research and ideation to prototyping, testing, and implementation, ensuring an exceptional user experience across all touchpoints.Strategic Cross-Functional Partnership: Serve as an equal partner to senior leaders in Product and Engineering, influencing product strategy and collaborating deeply to build innovative products that customers love and are willing to invest in, including those leveraging AI.Cultivating a Culture of Innovation: Instill and amplify a culture of innovation within the Design team and across the organization, actively identifying and celebrating groundbreaking ideas—especially those that explore the frontiers of AI in user experience.Partner with Design System: Facilitate healthy contribution to the Design System, ensuring its growth accommodates new interaction patterns and components required for AI-driven experiences, in close partnership with Engineering.User Research & Insights: Advocate for and drive user research initiatives to deeply understand customer needs, behaviors, and pain points, translating insights into actionable design improvements.Building Organizational Trust & Advocacy: Develop strong, trusted relationships across the entire organization, leveraging your influence and industry connections to advocate for the design team and champion the value of design thinking, particularly in the context of intelligent systems.What you need to bring:
We are looking for a seasoned design leader who is passionate about user experience, team development, and the transformative potential of technology. You should have:
Extensive Product Design Expertise, Mentorship & Holistic Thinking: At least # years of practical, in-house product and/or consumer-facing UX/UI and visual design experience, with a minimum of # years in a people management role on a Design team. You'll demonstrate an eagerness and ability to work across all digital, AI-powered, and, where applicable, physical manifestations of what we design, ensuring cohesive and intuitive experiencesEnterprise advocacy and influence
, especially within technology-driven sectors, is highly preferred. You should also possess a passion for mentoring executives, product managers, and engineers to deliver truly user-centered…
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