Lead Product Designer

Overview

Lead Product Designer Jobs in Toronto, Canada at Upwork

Title: Lead Product Designer

Company: Upwork

Location: Toronto, Canada

Category:

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.

Upwork’s platform has facilitated more than $25 billion in economic opportunity for talent around the world. Learn more at and follow us on , , , , and .

We’re looking for a Lead Product Designer to join our Growth & Monetization team, which is responsible for converting the value we deliver to customers into durable, scalable revenue through fees, ads, pricing, packaging, and promotions.

As a UX Lead Product Designer in this space, you’ll design and optimize high-impact growth loops and monetization surfaces across our two-sided marketplace, focusing on acquisition through retention. You’ll partner closely with Product, Data Science, Engineering, Marketing, and Research to run experiments, ship measurable improvements, and evolve pricing and packaging experiences that are clear, fair, and motivating for customers.

Responsibilities

Own end-to-end product design from identifying funnel opportunities and forming hypotheses through rapid concepting, launch, and iteration, delivering high-quality designs that balance speed, craft, and measurable impact.

Collaborate deeply with cross-functional partners (PMs, engineers, researchers, data scientists, and other designers) to define problems, prioritize opportunities, and ship experiments that move key metrics.

Use quantitative data, qualitative insight, and emerging technologies to identify friction and unlock opportunities across acquisition, activation, retention, and monetization flows, including prototyping and testing AI-powered or automated experiences where they accelerate outcomes.

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.

Design, test, and refine targeted experiences
, from onboarding and upsell flows to pricing, incentives, and lifecycle touchpoints, ensuring clarity, trust, and strong value exchange for users.

Create and socialize clear, lightweight design artifacts that support rapid decision-making, align stakeholders, and enable fast execution, prioritizing learning and outcomes over documentation for its own sake.

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 and optimizing growth funnels (activation, conversion, retention, monetization), with clear examples of measurable impact.

Strong experimentation toolkit (A/B testing, rapid iteration, metric selection, segmentation, and interpreting results), comfortable shipping in fast cycles.

A portfolio demonstrating growth-oriented, end-to-end product design with strong craft, showing how you used data and qualitative insight to drive iteration.

Ability to design transparent, trustworthy value exchange in monetization experiences (pricing/packaging, paid visibility, incentives), balancing customer outcomes with business goals.

Strong communicator and collaborator
, able to influence product strategy through data-informed design decisions and close partnership with PM, Engineering, Analytics, and Marketing.

Mastery of tools like Figma
, plus experience with user testing and AI prototyping tools like v0, Figma Make, or similar.

Comfort designing and experimenting with AI-powered experiences
, including intelligent workflows, LLM-driven features, or collaborating cross-functionally with ML/AI…