Principal Product Designer (AI)

TL;DR

Principal Product Designer (AI): Designing an intelligence layer for merchants that evolves from an assistant into an agent capable of taking action with an accent on agentic AI interaction patterns and trust. Focus on defining new interaction models for AI agents, raising the craft bar across the Retail design org, and shaping mobile POS strategy.

Location: Toronto preferred; open to other locations in Ontario, Quebec, and Eastern Canada

Salary: $200,000 - $240,000 CAD

Company

A one-stop cloud commerce platform helping retail, hospitality, and golf businesses simplify and scale operations globally.

What you will do

• Define interaction patterns for agentic AI, focusing on how merchants direct and supervise intelligent agents.
• Lead end-to-end design for the AI experience from concept and prototype to polished, shipped product.
• Elevate the craft bar across the Retail organization through direct hands-on contribution in various product areas.
• Develop ambitious vision work and prototypes to shape overall product strategy.
• Utilize AI-first workflows and modern tools to rapidly move from intent to working prototypes.
• Support and shape the mobile point-of-sale strategy through design thinking and hands-on exploration.

Requirements

• 12+ years of product design experience with a strong maker's mindset.
• Exceptional portfolio demonstrating high-level craft across UX, interaction, and visual design.
• Experience leading large, ambiguous initiatives across multiple teams without formal authority.
• Fluency with AI: active use of LLMs and AI prototyping tools in daily workflow.
• Technical proficiency to build prototypes and reason about engineering constraints.
• Ability to influence senior stakeholders through clear communication and storytelling.

Culture & Benefits

• Flexible work environment with remote work policies and flexible paid time off.
• Equity options and contributions to a pension plan.
• Comprehensive health, dental, wellness, life, and disability insurance.
• Enhanced parental leave to support growing families.
• Learning budgets and continuous training opportunities to grow your career.
• Computer purchase program for a personal Macbook.