Founding Product Designer (AI-Native)

About the Role: Founding Product Designer (AI-Native)

As our Founding Product Designer in Toronto, you'll be our first in-house designer (design has been contractor-run until now) and you'll own the function end to end: the consumer trade-in experience on sellit9.com, the embedded flows our merchant partners run on their own storefronts, and the design system that keeps it all consistent. The role is deliberately a product and design hybrid: you'll help decide what we build and why, then design how it works. You'll work directly with the CTO, engineering and product team, and your work ships to production every day.

This isn't a "make it pretty" role. You'll live in the conversion data, watch real user sessions, and defend every design decision with evidence. You'll also design for a surface most designers haven't touched yet: our trade-in flow runs inside Claude through our AI connector, and you'll help define what commerce looks like when the customer brings an AI agent to the journey.

Design here serves two audiences: people and agents. Our design system lives in code, our brand rules ship as agent skills, and our assets come out of versioned pipelines instead of one-off files. What you decide once gets applied everywhere, automatically.

What You'll Do

• Own product problems end to end: framing and specs, research, flows, prototypes, high-fidelity UI, and production handoff.
• Act as product owner for your surfaces: prioritize with the CTO, write the specs, define success metrics, and follow the results after launch.
• Design and iterate on the consumer funnel (quote, checkout, confirmation) to raise conversion, validating with A/B tests and session replays.
• Design merchant-facing surfaces: embedded trade-in flows, white-label experiences, and partner dashboards.
• Build and evolve our design system in Figma and keep it in lockstep with the production component library.
• Prototype in code with AI tools (Claude Code, Figma Make) so ideas get tested as working software, not static mockups.
• Shape our agentic commerce experience: trade-in quotes and orders that happen inside AI assistants.
• Package our brand and design rules as agent skills so every AI workflow on the team produces on-brand output by default.
• Run our asset pipeline: hero videos built in Remotion, page imagery generated under locked brand styles, everything versioned like code.
• Run usability tests and dig through GA4 and Microsoft Clarity to find where users struggle.
• Contribute to brand direction, marketing assets, and landing pages when needed. Small team, many hats.

Apply if you

• Have 5+ years of product design experience with shipped work in e-commerce, marketplaces, or fintech.
• Have product sense beyond the pixels: you can write a spec, scope an MVP, argue a prioritization call, and own a metric.
• Work AI-natively. Claude Code, Figma Make or similar are already part of how you design every day, and you've turned that into repeatable workflows (skills, custom agents, prompt libraries), not just occasional chats. This is non-negotiable.
• Know Figma deeply: components, variables and tokens, auto layout, and a portfolio of conversion-focused work.
• Have design systems experience: you've built or owned one and kept it consistent across web and mobile.
• Are fluent in funnel metrics: conversion rates, A/B testing, session replay analysis, and the discipline to let data settle debates.
• Do hands-on user research: usability testing, interviews, and turning findings into shipped improvements.
• Have enough HTML, CSS, and React literacy to prototype with AI assistance and review what engineering builds.
• Write strong UX copy. Microcopy is part of the design.
• Are fluent in English (written and spoken).

Even better if you have

• Experience designing AI-powered products: chat or agent interfaces, conversational commerce, or prompt-driven UX.
• Motion design skills for product videos and hero animations (we build ours in code with Remotion).
• Accessibility habits: WCAG basics baked into your components from the start.
• Content modeling for a headless CMS. Our marketing pages are spec-driven components rendered from Strapi.
• Experience wiring design tools to agents: Figma MCP, Code Connect, or your own scripts.
• B2B2C or white-label experience: one product, many brands, strict theming constraints.
• Time spent as a PM, a founder, or the only designer at an early-stage startup.