Lead Product Designer

Summary

Join Upwork, the world’s largest work marketplace, as a Lead Product Designer on the Work Management team. You will define and execute the design strategy for pre- and post-contract workflows, leading end-to-end design execution and driving experimentation. Collaborate with cross-functional partners, translate user insights into impactful solutions, and provide design mentorship. This role requires proven experience designing user flows for complex workflows, expertise in product experimentation, and a strong portfolio. Upwork offers a remote-first work environment, comprehensive benefits, and opportunities for professional growth.

Requirements

• Proven experience designing user flows and interfaces for complex, multi-step workflows—particularly in contract or project management environments
• Expertise in product experimentation, including running A/B tests and applying data to improve design outcomes
• A compelling portfolio demonstrating product design excellence across web and mobile platforms, with clear rationale behind design decisions
• Strong cross-functional collaboration skills with a track record of influencing product strategy through user-centered design
• Deep proficiency with tools like Figma and experience leading research and usability testing initiatives to inform design

Responsibilities

• Define and execute the design strategy for pre- and post-contract workflows, aligning with both user needs and business goals
• Lead end-to-end design execution, creating wireframes, prototypes, and high-fidelity visuals that improve complex workflows
• Drive experimentation and A/B testing initiatives to validate design hypotheses, improve usability, and support data-informed decisions
• Collaborate with cross-functional partners—including product managers, engineers, researchers, and analysts—to influence product direction and ensure design is embedded early in development
• Translate user insights into impactful solutions that streamline contract lifecycle touchpoints and reduce user friction
• Provide design mentorship across the team by sharing feedback, insights, and best practices
• Stay current on design trends, tooling, and emerging technologies to continuously elevate the quality of your work and that of the broader team

Benefits

• Comprehensive medical coverage for you and your family
• Unlimited PTO
• A 401(k) plan with matching
• 12 weeks of paid parental leave
• An Employee Stock Purchase Plan