Lead Product Designer (P4)

Upwork; Toronto; On-site; CAD 85,000 - 110,000; Full time

Job summary

A global work marketplace in Toronto is seeking a Lead Product Designer to elevate design strategies for a two-sided platform. This role involves leading end-to-end product design processes, collaborating cross-functionally, and leveraging data to enhance client and talent interactions. The ideal candidate has experience with complex workflows and a robust portfolio showcasing design work across web and mobile platforms. Join us to reshape how work gets done while exploring AI-powered solutions.

Qualifications

• Proven experience in contract and project management design.
• A compelling portfolio showcasing end-to-end product design.
• Strong communicator and collaborator.

Responsibilities

• Lead end-to-end product design from discovery to launch.
• Collaborate with PMs, engineers, and researchers.
• Leverage data and user insights for design decisions.

Skills

Designing complex workflows

Prototyping with AI capabilities

User research

A/B testing

Collaboration across teams

Tools

Figma

AI prototyping tools

Job description

Upwork ($UPWK) is the world’s human and AI-powered work marketplace that connects businesses with highly skilled, AI-enabled independent talent from across the globe. From entrepreneurs to Fortune 100 enterprises, companies rely on Upwork’s trusted platform and its mindful AI companion, Uma, to find and hire expert talent, leverage AI-powered work solutions, and drive business transformation. With on-demand access to professionals spanning more than 10,000 skills across AI & machine learning, software development, sales & marketing, customer support, finance & accounting, and more, Upwork enables businesses of all sizes to scale, innovate, and build agile teams for the age of AI and beyond.

We’re looking for a Lead Product Designer to join our Marketplace team, which is responsible for shaping the experiences across all sides of our two-sided platform—connecting clients and talent around the world to get work done. As a Lead Product Designer, you\'ll own and elevate the design strategy for workflows that are core to our customers\' success.

In this role, you\'ll help shape the future of work by designing intuitive, seamless interactions that enhance how clients and talent collaborate on Upwork—from project setup to successful delivery. You’ll also have the opportunity to explore how emerging technologies like AI, large language models (LLMs), and intelligent automation can unlock new value and simplify complex workflows across the marketplace.

Join us in reimagining how work gets done—and make a meaningful impact on millions of users around the world.

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.

Come change how the world works.

This position will initially be employed through a partner to ensure a seamless hiring process while we establish the hub. Once the hub is established, there may be opportunities to transition to employment with Upwork depending on business needs and other requirements. While employed by the partner, you’ll work as part of Upwork’s team, with access to our resources, culture, and growth opportunities.

Upwork is an Equal Opportunity Employer committed to recruiting and retaining a diverse and inclusive workforce. We do not discriminate based on race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, or other legally protected characteristics under federal, state, or local law.

Please note that a criminal background check may be required once a conditional job offer is made. Qualified applicants with arrest or conviction records will be considered in accordance with applicable law, including the California Fair Chance Act and local Fair Chance ordinances. The Company is committed to conducting an individualized assessment and giving all individuals a fair opportunity to provide relevant information or context before making any final employment decision.

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