Intro
Upwork’s Next Frontier
For two decades, Upwork has been a crucial tool for businesses around the world to connect with freelancers. With the rise of remote work, we've seen clear changes in customer behavior, prompting Upwork to rethink its business approach.
I was part of an exciting project to improve the new payroll MVP, with the goal of achieving product market fit and expanding the Upwork platform into the global payroll market.
My Role
I led design for this project from January 2022 to June 2023, partnering closely with research to conduct interviews and translate insights into actionable designs. I also worked with product management to challenge assumptions and helped pivot a key feature that led to improvements in a critical product metric.
The redesign was completed and soft launched within 6 months.
Problem
Hiring Global Talent Is High-Risk and Hard to Scale
Small and mid-sized businesses struggle to hire global freelancers due to complex legal requirements, limited HR support, and fragmented tools, leading to delays, compliance risk, and lost growth opportunities.
Key Frictions in the Current Experience
Inconsistent context emerged from different entry points. AnyHire is a standalone product outside the core platform, and existing clients who accessed it through the global navigation dropdown often arrived without clarity on what it does or who it is for.
Upon entry, users were dropped straight into a contract form. Without sufficient context or readiness, the length and complexity of the form created cognitive overload and hesitation to begin.
Even among users who completed the form, the final review step introduced new friction. The system’s automatic classification recommendation was confusing for some and difficult to override for others, as the override option was hidden behind the "Edit" button.
Surfacing the total cost at this late stage also created sticker shock and hesitation.
Redesign
Clarity > Speed
Given limited engineering capacity, we initially prioritized lightweight guidance and orientation, focusing on ideas that were high impact and low effort. However, testing revealed that for a high stakes task like drafting an employment contract, the experience still moved too quickly. Users needed confidence before taking the first step, not after. To fix this, I added a one-time onboarding flow before entering AnyHire to slow users down and establish clarity upfront.
What the intro needed to accomplish:
Explain why and when someone should use AnyHire
Help users self identify whether they were the right audience and ready to proceed
Preview estimated costs early to prevent sticker shock later in the flow
Redirect users who were not a fit back to Upwork, where alternative hiring options were more appropriate
Support rather than constrain
While iterating the Create Offer flow, we initially kept automated classification mandatory to reduce misclassification risk, based on prior research. Testing later showed that while this protected some clients, it created unnecessary friction for experienced users who already knew their desired classification. Repeated overrides felt redundant and discouraging.
Driven by this insight, I made classification optional and restructured the long form into a clearer, step by step flow using existing design system components, reducing cognitive load and improving usability.
From Hesitation to Confidence
By front loading cost transparency and critical decisions, the final review screen became a moment of confidence, not friction. Clear confirmations, classification explainers, and support links reinforced trust and empowered users to send offers with certainty.
Result
Impact That Uncovered Hidden Demand
Takeaway
Slow is fast when stakes are high. Prevention is better than correction. Friction is valuable when it creates clarity.
Sensitive tasks require care, clarity, verification, and oversight. Moving forward, I will front load these elements so experiences reduce fear and build confidence at every step.
