Upwork.com
Anyhire
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 expand the Upwork platform into the global payroll market.
Rethink to Retent
The COVID-19 pandemic from 2020 to 2021 triggered a remote work revolution, leading many businesses to seek out freelance talent on platforms like Upwork.
As a result, competitors such as Fiverr, Toptal, and Freelancer.com also grew quickly to meet this demand.
By 2022, interest began to fade, and companies shifted their focus toward hiring payroll employees. Meanwhile, competitors like Deel, which target enterprise payroll clients, started landing high-value accounts.
With retention rates slipping, Upwork had to rethink its strategies to stay competitive and relevant.
The Challenge
Bottling the Freelancer Magic for the Payroll World
Our goal for the project was to make it as easy to hire any freelancer on Upwork as hiring anyone outside of the Upwork platform, as a payroll employee.
Our high level goals were to:
1. Helps clients to quickly and easily hire talent from around the world
2. Support clients with legal compliance requirements
3. Cutting down on time and costs is essential for helping clients hire more efficiently.
My Role
I led the design for this project, from January 2022 to June 2023, collaborating closely with different product designers, researchers, content designers, during various phases.
The app launched globally on April 28th, 2022.
Although I continued to overseeing the project after the soft launch, I transitioned to focus on new projects.
Kickoff
At the start of the project, I inherited a set of early design mocks and foundational research from a previous team that had briefly explored the concept.
While these assets gave me a valuable starting point, many core questions remained unanswered.
Recognizing the need for deeper insight, I investigated the complexities of global hiring to get a better understanding of the people and problem involved.
The Discovery
Why Freelancers Get Left Behind
Trust is the missing link.
Clients were often reluctant to give freelancers strategic or long-term projects. Not because of skill gaps, but because of a lack of trust.
Payroll employees are seen as stable and accountable. Freelancers? Temporary task-doers. Without built-in systems for contracts, benefits, or long-term support, platforms unintentionally reinforced this gap.
By designing for reliability and accountability, I saw an opportunity to shift how freelancers are perceived, from one-off helpers to trusted partners. That shift could unlock deeper projects and more meaningful client relationships.
Hiring Globally Isn’t One-Size-Fits-All
Different countries have different payroll systems, employment laws, and tax rules, but there’s no central hub for clients or freelancers to get reliable guidance. Most platforms left users to figure it out themselves.
Clients turned to Google or third parties, which led to delays, compliance risks, and extra costs. Client were left unsure about potential penalties and often left unprotected.
This confusion drove both sides toward slower, traditional vendors. I realized the real fix wasn’t a quick feature, it was building a foundation of trust and support that made global hiring feel safe, clear, and scalable.
The Hidden Cost of DIY Contracts
Clients often had to draft or review contracts on their own, usually by copy-pasting terms or relying on messy email threads with no legal support.
This led to misaligned expectations, delayed onboarding, and disputes over payment structures. Each unclear agreement chipped away at trust and weakened the platform’s credibility.
I saw an opportunity to fix this with intuitive, legally guided tools that could streamline the process, reduce friction, and give both sides more confidence in working together.
Compliance Was an Afterthought
Clients were worried about misclassifying freelancers or violating local labor laws, but most platforms offered no safeguards to prevent it.
Without built-in checks, alerts, or legal guidance, users faced the risk of fines, reputational damage, or even business bans. These risks made companies hesitant to scale their freelance programs.
I started to see compliance not as red tape, but as a core UX layer, one that could build trust and open doors to enterprise adoption.
Define
Problem Statement
Small and mid-sized business owners often find it challenging to hire global freelancers because of complex legal requirements, limited HR support, and unreliable tools. As a result, they face delays, compliance risks, and missed opportunities that can hinder long-term growth.
HMW make hiring freelancers from around the world just as easy, safe, and scalable as hiring someone nearby?
Hiring Was All Over the Place
The hiring process involved multiple stages, shifting priorities, and several stakeholders. It often led to confusion, scope creep, and a loss of focus on the core goals.
To bring clarity, I mapped out a simplified journey, pinpointing the moments that mattered most so I could focus on high-impact opportunities.
Design
Introducing: Any Hire
Any Hire makes global hiring easier for small and mid-sized businesses by taking care of contracts, compliance, and payroll in over 180 countries. This means you don’t need to establish local entities, which cuts down on legal risks and operational costs.
By managing the tricky aspects like classification, taxes, and benefits, Any Hire makes bringing in international talent as simple and secure as hiring someone from your local area.
How we got here
After speaking with startup founders, HR leads, and small business owners hiring globally, and reviewing past research, I realized users weren’t just looking for a payroll tool. They wanted a simple, reliable way to hire and pay international employees without the headache of compliance or legal complexity.
I organized these insights using a jobs-to-be-done framework and used it to guide the MVP design, focusing on only what users needed to accomplish their core task.
Designing for Agility: Standalone by Intent
I mapped out the goals, expectations, and success criteria for each persona and quickly saw tension between the needs of freelancer clients and payroll buyers. Building a new MVP within the existing freelancer platform risked confusing users and negatively impacting current key metrics.
We made a strategic call to design the MVP as a standalone product. This gave us the freedom to focus entirely on payroll clients, shaping the messaging, user flows, and success metrics around their needs, without being constrained by legacy code.
Intent-Based Onboarding
We saw early confusion between Any Hire and Upwork’s core freelance platform, especially from users exploring both at once.
Many assumed Any Hire was built for freelancers, simply because it was part of the Upwork ecosystem. Freelance clients were signing up for the wrong product, drawn in by the buzz, clean interface, or lower cost, despite messaging that explained its purpose for payroll clients only.
To fix this, I designed a lightweight onboarding flow focused on clarifying the audience and setting the right expectations.
By using intent-driven questions and contextual cues, we helped users self-select the right path and quickly understand what Any Hire was, and wasn’t, for. This also served as a filter, cutting down support tickets from users who ended up in the wrong flow, and a redirect to help freelancer clients get back to the main platform.
Smart Compliance: A Flexible Engine, Not a Gatekeeper
The best tools don’t just enforce, they inform and adapt to real-world decisions. Legal compliance came up as a top concern in nearly every client interview.
Because worker classification depends on variables like location, role, and responsibilities, we built a compliance engine that asked the right questions and delivered tailored recommendations.
I designed a step-by-step interface that felt more like a quick consult than a checklist: clear, approachable, and respectful of the client’s final say. This balance gave users the guidance they needed without taking away their autonomy.
Pay Without Borders: Automating Global Payroll
In mission-critical flows like payroll, the best UX is almost invisible, it works so smoothly users barely notice.
Global payroll is often full of friction, from currency conversion issues to late deposits. Freelancers frequently voiced frustration about delays and inconsistent payments.
Rather than reinvent the wheel, we built on Upwork’s trusted payments infrastructure to automate deposits behind the scenes, keeping things seamless for users.
On the design side, we focused on reliability signals, clear status indicators, confirmations, and payout timelines, to build trust and reduce payment anxiety.
Simplifying the Complex:
3 Steps: Hire, Pay, Manage
Early testing revealed that even small amounts of upfront information could overwhelm users, especially when dealing with global hiring.
To reduce friction, I leaned on progressive disclosure, surfacing the right details at the right time. I worked closely with legal and operations teams to identify which information could be revealed just-in-time, mapped across a simple Hire, Pay, and Manage flow.
We built this journey around user expectations, not backend logic. The result was a guided experience that felt intuitive, reduced confusion, and gave users the confidence to move forward without guesswork.
Trust Is Earned, Not Assumed
When users can understand and anticipate what’s happening, trust comes naturally, even in complex systems.
Transparency was key to closing the trust gap, especially for new users managing sensitive tasks like compliance and payments.
We used anticipatory design to stay one step ahead, answering common questions before users needed to ask, elements like cost previews, benefit breakdowns, classification comparisons, and in-context disclosures to reveal what the system was doing behind the scenes.
This clarity helped users feel informed, in control, and confident in every step.
Risk Offloading and Safety Net Design
Confidence doesn’t come from ignoring risk, it comes from knowing you’re protected when things go wrong.
To support non-experts making high-stakes decisions, we applied a risk-offloading framework that shifted legal and compliance burdens from the user to the platform.
I partnered with legal to reframe messaging, moving from vague advisory language to proactive reassurance. We visualized EOR partnerships as protective shields, clearly showing what coverage clients had and when it would apply.
We also highlighted a legal protection, not buried in fine print, but displayed as a visible safety net to ease fear and support confident decision-making.
Localization That Doesn’t Feel Like Work
True simplicity comes from systems that adapt to users, not the other way around.
I partnered with legal and engineering to handle complex localization variables like benefits, taxes, currencies, and languages behind the scenes. On the front end, I designed a smart contract wizard that removed legal friction and made the process feel like guided customization.
Where users typically expect roadblocks, the experience felt streamlined. Contracts, compliance, and Employer of Record (EOR) setup were all integrated into one adaptive flow, helping clients onboard talent in minutes instead of days.
Deliver
The Pivot: A Quiet Launch and a Strategic Shift
The launch was intentionally low-key, and momentum never fully picked up. In a last-minute shift, leadership chose to move away from positioning Any Hire as a standalone payroll solution for external talent.
The focus turned inward, toward enabling full-time employment for freelancers already on the Upwork platform. That shift led to my next project, Full Time—but that’s a story for another day.
At the time of the pivot, about 250 early adopters were actively using Any Hire, most of whom joined during the testing and pre-launch phases.
