Upwork
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, the pandemic-driven surge in freelance hiring began to level off, and more companies started to shift toward hiring payroll employees. Meanwhile, competitors like Deel, which target enterprise payroll clients, started landing high-value accounts.
With retention rates shifting, Upwork is proactively evolving its strategy to lead in a changing talent landscape.
The Challenge
Bottling the Freelancer Magic for the Payroll World
The goal for the project was to make hiring a payroll employees outside of Upwork, as easy as hiring a freelancer on Upwork.
Our high-level goals were:
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 with 2 researchers and 2 content designers from time to time.
The app launched globally on April 28th, 2023.
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 Employers Choose Payroll Over Freelancers
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 prioritizing reliability and accountability, we can explore more meaningful projects and forge stronger connections between clients and their employees.
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?
The Journey Of A Global Hire
The hiring process went through multiple stages, shifting priorities, and involved several stakeholders, often leading to confusion, scope creep, and a loss of focus on the core goals.
Given the amount of time and resources required, the most friction-heavy phases turned out to be entity setup and contract drafting. These areas clearly represent the highest-impact opportunities for improvement. One unexpected insight: it often takes clients much longer than anticipated to deliver official international offers.
The biggest realization was that not all stages deserve equal attention, most of the friction stemmed from the client side. By focusing on these high-friction points, we can help clients cut down on time and resource demands, while also speeding up the path to hiring the right talent.
Guiding Principles
A few design principles I used to maintain a clear vision, prioritize the right features, and get stakeholder buy-ins:
Clarity Over Complexity
Cross-border hiring is filled with legal, financial, and logistical hurdles. The goal is to strip away unnecessary steps and make each interaction feel approachable, not overwhelming.
Global-First Experience
Hiring rules vary widely by country, what works in Canada won’t fly in Brazil. The product needs to adapt to different regional realities without losing cohesion.
Minimize Risk
When it comes to legal compliance and payroll, the stakes are high. Most clients aren’t experts in global labor laws or compliance frameworks. We need to design for the worst-case scenarios, embedding safeguards, fallback plans, and clear guidance, to give users peace of mind, no matter their level of experience.
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
Designing for Agility: Standalone by Intent
While hiring may appear similar on the surface, I broke down the subtle differences between hiring international employees and contractors, and quickly saw tension between how we currently serve freelancer clients and the experience we needed to create for payroll buyers. The two groups had fundamentally different mental models, workflows, and definitions of success.
We considered whether the existing platform could support both audiences, but doing so would introduce confusion, compromise usability, and risk hurting key metrics. While technically possible, it would have required a full redesign, an ambitious undertaking that didn’t align with our MVP goals.
So we made a strategic decision: to design the MVP as a standalone product. This gave us the freedom to focus entirely on payroll clients, tailoring messaging, user flows, and success metrics to their needs without being constrained by legacy systems or diluting value for either segment.
Simplicity as a Non-Negotiable
After speaking with startup founders, HR leads, and small business owners hiring globally, and reviewing past research, I found a common thread across all personas: no one wanted a complex payroll tool.
What they needed was a simple, reliable way to hire and pay international employees without the headache of compliance or legal red tape.
But simplicity isn’t just about making things look clean, it’s about focusing on what’s essential. To do that, I used the JTBD framework to break down user insights and rank them by impact. This helped us design an MVP grounded in real user needs, not bloated with features, keeping the experience focused, purposeful, and easy to navigate.
Intent-Based Onboarding
Even as a standalone product, users exploring both Any Hire and Upwork’s freelance platform often got confused. Many assumed Any Hire was just another tool for freelancers, understandable, given the shared branding and familiar interface.
Freelance clients were signing up for the wrong product, drawn in by the clean UI, lower price point, or Upwork name, despite messaging that clearly framed it for payroll use. Their mental models were already set.
We realized this wasn’t just a copy issue, it was a clarity gap at a key decision point. So I designed a lightweight onboarding flow to educate users from the start.
Through intent-driven questions and contextual cues, we helped users self-select the right path and understand exactly what Any Hire was, and wasn’t, for. It cut support tickets and, more importantly, aligned expectations early, improving user confidence and overall fit.
Smart Compliance: A Flexible Engine, Not a Gatekeeper
Legal compliance wasn’t just a common concern, it was one of the most complex challenges that surfaced in nearly every client interview.
Worker classification depends on multiple variables, like location, role, and responsibilities, so there’s rarely a one-size-fits-all answer. Some clients wanted to bypass classification altogether, while others needed education to even understand what classification meant.
To make this manageable, I designed a step-by-step wizard turn a complex process into something that felt more like a consult than a form: clear, approachable, and flexible. It offered tailored guidance without overwhelming users, while ensuring clients kept full control. This struck the right balance between compliance and 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 nudged clients to set up payment before sending the contract to talent to make sure payments were processed on time and in the background, without added steps or follow-ups. As a result, both sides received strong reliability signals: clear status updates, payout timelines, and confirmations that helped build trust and ease 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
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 handling sensitive tasks like compliance and payments.
We try to stay one step ahead of user needs, surfacing answers before questions came up. Cost previews, benefit breakdowns, classification comparisons, and in-context disclosures helped users understand what the system was doing behind the scenes.
This clarity made users feel informed, in control, and confident in every step.
Offloading Risk
To support non-experts making high-stakes decisions, we shifted the burden of legal and compliance risk away from users and onto the platform itself.
I worked closely with legal to frame our messaging as clear, proactive reassurance, bringing legal protection front and center. Instead of burying it in fine print, we positioned it as a visible safety net to reduce anxiety and help clients move forward with confidence.
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 pivot, 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.
