Lead Product Designer at Upwork – Remote

Job Description

Upwork ($UPWK) is the world’s largest work marketplace, connecting businesses with highly skilled professionals worldwide. From entrepreneurs to Fortune 100 enterprises, companies trust Upwork’s platform to access expert talent, leverage AI-powered work solutions, and drive meaningful business outcomes.

Upwork’s AI-powered platform has facilitated over $20 billion in economic opportunity for professionals worldwide. With professionals spanning 10,000+ skills, including AI and machine learning, software development, sales and marketing, customer support, finance and accounting, and more, Upwork empowers businesses of all sizes to scale, innovate, and build agile teams.

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.