Principal Product Designer, Retail

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.

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 ...