Leroy Matthews
Senior Product Designer
001
Simplified screening process which generated better matches for everyone
Upwork is the world’s largest work marketplace where clients post jobs and freelancers submit proposals for jobs they’re interested in. Clients struggle to identify and confidently vet the right freelancers when reviewing proposals and freelancers struggle to understand client expectations with cryptic job descriptions.
Freelancer profile redesign that surfaced the right signals at the right time
When hiring on Upwork is an online marketplace where businesses find, hire, and pay freelancers for all kinds of work., freelancer profiles are the primary way clients evaluate freelancer’s relevant skills and experience. They can view their profiles through search or their proposal manager, which is where they review all the proposals (i.e., applications) submitted for their job. In both cases, the profile is displayed as a slider to help clients view more profiles quickly. The slider design made it difficult for clients to find freelancer’s relevant experience. This led to a 40% fill-rate for high-value jobs (jobs with $1K+ budgets) leaving clients with unfilled jobs and qualified freelancers without a job.
Helping freelancers manage their virtual tokens and build their reputation
Freelancers on Upwork is an online marketplace where businesses find, hire, and pay freelancers for all kinds of work. use Connects, virtual tokens, to apply for jobs and ad product to promote themselves to clients. Buying Connects, checking their history, and earning free Connects happened on three separate pages, making for a frustrating experience. New freelancers also lacked education around Connects, making it hard to know where to start. Without a central place to manage their Connects, many freelancers applied to fewer jobs and missed opportunities to earn more Connects and build their reputation.
Snapshot of freelancers on-platform experience that builds better matches
Before starting a contract on Upwork is an online marketplace where businesses find, hire, and pay freelancers for all kinds of work., clients review freelancers’ skills and experience to make sure they’re a fit for the job. They often struggle to find and trust signals that a freelancer's skills fit their job. 40% of clients who didn't send an offer said applicants didn't show relevant experience. About 50% of clients using search weren't sure they could find the right freelancer.
A new ad format empowering freelancers to better market themselves
Upwork is an online marketplace where businesses find, hire, and pay freelancers for all kinds of work. offers freelancers a variety of ad products to increase their visibility when applying for jobs. While these products made freelancers more visible they didn't let freelancers introduce themselves. Beyond skills and experience, clients wanted to know what freelancer's personality and communication style were before hiring.
Highlighting my latest work and creativity with the help of AI
After being laid off from my job in June of 2026 I needed to update my portfolio website to begin looking for my next opportunity. I needed to update my site with my latest work from the past six years but I also wanted to redefine my personal brand to represent the designer I had grown into, over that same time. Ultimately, I wanted to create a memorable digital experience that reflected who I am as a designer.
