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Lead Product Designer (P4)

9 months

In short

Lead Product Designer role to shape user experiences across a two-sided platform, focusing on intuitive and AI-powered workflows that connect clients and talent globally. Collaborate cross-functionally and drive design strategy and innovation.

Where
Onsite · Canada — Toronto
Pay
Not stated. Typically $150k - $200k USD
Level
Senior-level · Full-time
Upwork
Upwork
  • HR & Work

Connects businesses with global freelance talent through its online work marketplace.

0 open roles · usually open about 4 weeks

Responsibilities

  • Lead end-to-end product design from discovery and concepting through launch and iteration—delivering high-quality wireframes, prototypes, and polished experiences with strong craft.
  • Collaborate deeply with cross-functional partners (PMs, engineers, researchers, data scientists, and other designers) to frame problems, explore ideas, and shape product direction through implementation.
  • Leverage data, user insights, and emerging technologies to inform design decisions and uncover opportunities to improve contract lifecycle workflows. This includes prototyping with AI-powered capabilities and integrating intelligent automation where it adds value.
  • Drive experimentation and continuous improvement by running A/B tests, conducting qualitative user research, and using rapid prototyping to validate hypotheses and evolve the product based on real-world feedback.
  • Build and share design artifacts—from early concepts to detailed specs—that bring ideas to life and keep stakeholders aligned.
  • Mentor others and contribute to design culture, sharing best practices, giving constructive feedback, and championing design quality across the team.

What IT Takes to Catch Our Eye

  • Proven experience designing complex, multi-step workflows, ideally in contract, project management, or marketplace environments.
  • Strong experimentation mindset—comfortable with A/B testing, user research, and using data to refine designs.
  • A compelling portfolio that demonstrates end-to-end product design across web and mobile—highlighting interaction, visual, and UX design with clear rationale for your decisions.
  • Strong communicator and collaborator, with a track record of shaping product strategy through design.
  • Mastery of tools like Figma, plus experience with user testing and AI prototyping tools like V0, Galileo, or similar.
  • Familiarity with designing for AI-powered experiences, including intelligent workflows, LLM use cases, or cross-functional collaboration with ML/AI teams.
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