[Remote] Lead Product Designer (P4) at Upwork

Remote

Not SpecifiedCompensation

N/AExperience Level

N/AJob Type

Not SpecifiedVisa

N/AIndustries

Requirements

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

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
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

Upwork

Online platform connecting freelancers and clients

About Upwork

Upwork connects freelancers with clients looking for various services in the gig economy, which focuses on short-term contracts instead of permanent jobs. The platform allows freelancers to create profiles that showcase their skills, while clients can post job listings for specific projects. Freelancers bid on these projects, and clients choose the best candidates based on proposals and reviews. Upwork earns revenue through service fees charged to freelancers based on their earnings, with a tiered structure that rewards long-term client relationships. The platform also offers premium memberships and additional services for enhanced visibility and access to job listings. Upwork provides tools for time tracking, invoicing, and project management, making it easier for both freelancers and clients to manage their work and payments. The goal of Upwork is to facilitate successful project completion by bridging the gap between freelancers and clients.

San Francisco, CaliforniaHeadquarters

2015Year Founded

$143.8MTotal Funding

IPOCompany Stage

Consulting, Enterprise SoftwareIndustries

10,001+Employees

Benefits

Health Insurance

Unlimited Paid Time Off

401(k) Retirement Plan

401(k) Company Match

Parental Leave

Employee Stock Purchase Plan

Risks

Increased competition from Fiverr and Toptal threatens Upwork's market share.

The new Fiverr-style Project Catalog may commoditize services, reducing freelancers' perceived value.

Strategic shifts under new management may not align with current client expectations.

Differentiation

Upwork connects freelancers with clients across diverse industries, enhancing global work opportunities.

The platform offers tools like time tracking and invoicing for efficient project management.

Upwork's tiered fee structure incentivizes long-term client relationships, differentiating it from competitors.

Upsides

Upwork's acquisition of Objective AI enhances its AI capabilities for better talent matching.

The introduction of Featured Jobs increases visibility for job posts, attracting more candidates.

Upwork's recognition as the top job posting site boosts its credibility among employers.

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