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Upwork is one of the largest networks for freelance work. I’ve been a freelancer on Upwork for about 8 years myself. In 2021 Upwork Enterprise Solutions hired me to help redesign their sophisticated onboarding.


It all started with sitting together with the entire team and discussing problems that we were facing in the onboarding. One of the major problems was that we had two types of onboarding with entirely different UX. It was a big struggle for hiring managers to use it. Things got especially complicated when there was a payroll involved. The most difficult part for freelancers was that sometimes they had to accept multiple offers for the same job as there was another agency involved in the hiring process.

problems sticky notes


Obviously, we had two main groups of users – freelancers and clients. However, the research through numerous video calls showed that clients had different goals and motivations. Some companies wanted to hire a full-time team member and other companies wanted to hire someone to help them with a short project. Also, hiring managers weren’t using the onboarding configuration as often as system administrators. Based on that, clients were divided into two groups – #1 hiring managers and #2 system administrators.

User Journey

After we had all problems on the table, I started to create user journeys to see at which step users were facing these problems. To help define the user journey for both clients (companies who hire) and freelancers, I had a few rounds of meetings with both parties.

user journey

user journey of freelancer

User Flow

The user flow from sending an offer to onboarding completion helped me to define how users interact with Upwork during the hiring process.

user flow

Information Architecture

When I had more understanding of the problem and pain points, it was time to take a look at the current user interface and build the information architecture. It should help to arrange the content better and create a more well-structured unified onboarding experience.

information architecture

UI Design

A key component of my work for Upwork Enterprise Solutions was applying a thorough research and feedback loop. We had numerous calls with hiring managers to test the newly designed onboarding dashboard and configuration pages.

upwork dashboard ui

upwork onboarding tasks ui

upwork onboarding configuration

mobile ui


The new unified onboarding received great feedback from its core users and stakeholders. It allowed automating getting the necessary information when re-hiring freelancers, thus decreasing the onboarding time from weeks to days. The unification also decreased the system’s complexity level for internal team members – it became easier to start using it without a mentor.


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