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 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.
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.
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.
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.
Discover
Understanding the Payroll Advantage
At the heart of this discovery was a simple but critical insight: clients don’t choose payroll employees over freelancers because of talent gaps, they choose them because of trust.
Payroll employees come with built-in signals of stability, accountability, and commitment. Contracts, benefits, legal protection, and internal systems all reassure clients that things won’t fall through.
Freelancers, on the other hand, often lack those same structural safeguards. They’re seen as temporary, transactional, and harder to manage at scale.
This isn’t just about perception, it’s about real operational risk.
When trust feels uncertain, clients default to what feels safer. To compete, we realized we couldn’t just match freelancers on flexibility or price, we had to offer the trust and accountability that traditional employment signals, while still preserving the benefits of freelance agility.
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 where clients or freelancers can get reliable guidance.
Most platforms left users to figure it out on their own. As a result, clients turned to Google or third-party providers, which introduced delays, compliance risks, and unexpected costs.
Many were unsure about potential legal penalties and felt exposed and unprotected.
This confusion often pushed both sides back toward slower, traditional vendors.
I realized the real solution wasn’t a quick feature, it was building a foundation of trust and support, one that made global hiring feel safe, transparent, and scalable for everyone involved.
The Hidden Cost of DIY Contracts
Clients were often left to draft or review contracts on their own, usually by copy-pasting terms or relying on fragmented email threads without legal guidance.
This lack of structure led to misaligned expectations, delayed onboarding, and disputes over payment terms.
Each unclear agreement didn’t just slow things down, it eroded trust and weakened the platform’s credibility.
I saw an opportunity to solve this by introducing intuitive, legally guided tools that streamlined the process, reduced friction, and gave both sides greater confidence and clarity when working together.
Compliance Was an Afterthought
Clients were increasingly worried about misclassifying freelancers or violating local labor laws, yet most platforms offered no built-in safeguards to prevent it.
Without clear checks, alerts, or legal guidance, users faced serious risks, fines, reputational damage, or even business bans. These uncertainties made companies hesitant to scale their freelance programs, despite growing demand.
That’s when I began to see compliance not as red tape, but as a critical UX layer, one that could build trust, reduce fear, and unlock enterprise adoption by making global hiring feel safer and more scalable.
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?
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
A Strategic Split to Build Trust
At first glance, hiring international employees and hiring contractors may seem similar, but once I mapped the workflows and mental models behind each, the differences became clear.
Payroll clients had different priorities, definitions of success, and compliance concerns compared to freelancer clients. This tension exposed a critical insight: the experience that worked well for freelancers was fundamentally misaligned with what payroll buyers needed.
We explored whether the existing Upwork platform could support both audiences. Technically, it was possible, but doing so would introduce complexity, confuse the user experience, and dilute the value for both segments. It would also require a full redesign, a major investment that didn’t align with our MVP goals.
Instead, we made a strategic decision to build the payroll experience as a standalone product. This gave us the freedom to tailor every part of the journey, messaging, flows, and success metrics, around the unique mindset of payroll buyers. It allowed us to move fast, stay focused, and, most importantly, build something that felt intuitive and trustworthy to the users who needed it most.
A Payroll Tool That Doesn't Feel Like One
No one wanted a complex payroll system. What they needed was simple, reliable global hiring without the headache of compliance, legal paperwork, or confusing workflows.
But simplicity isn’t just a visual choice, it’s a product philosophy. It means stripping away the noise and focusing on what’s essential.
To get there, I used the Jobs-to-Be-Done framework to break down user goals and rank them by impact.
This approach helped us define an MVP rooted in what users actually needed, not what sounded good on paper.
The result was a streamlined experience that gave users clarity, control, and the confidence to grow their teams globally, without second-guessing every click.
Fixing the First-Click Confusion
Even as a standalone product, users exploring both AnyHire and Upwork’s freelance platform often became confused.
Many assumed AnyHire was just another freelancer tool, understandable, given the shared branding and familiar interface.
Despite clear messaging that positioned it for payroll use, freelance clients were signing up for the wrong product, drawn in by the clean UI, lower price point, or the Upwork name. Their mental models were already set before they arrived.
We quickly realized this wasn’t just a copy issue, it was a clarity gap at a critical decision point.
To address it, I designed a lightweight onboarding flow that educated users from the very first click.
Through intent-driven questions and contextual cues, we guided users to self-select the right path and better understand what Any Hire was, and wasn’t, designed for.
The result was more than fewer support tickets, it was a shift in confidence. By aligning expectations early, we gave users a clearer sense of direction and built trust in the product from the start.
Helping Clients Navigate the Gray Areas
Legal compliance wasn’t just a recurring theme, it was one of the most complex and emotionally charged challenges that surfaced in nearly every client interview.
Worker classification depended on multiple factors, location, role, responsibilities, and there was rarely a one-size-fits-all answer.
Some clients wanted to skip classification entirely to save time, while others didn’t fully understand what it meant or why it mattered.
This tension revealed a deeper insight: clients didn’t want more rules, they wanted more clarity and control.
To address this, I designed a step-by-step wizard that transformed a legally dense process into something that felt more like a guided consultation than a static form, clear, approachable, and flexible.
It provided tailored guidance without overwhelming users, while still keeping them in control of their decisions. This struck the right balance between compliance and autonomy, making clients feel supported instead of scrutinized.
Building on What Already Works
In mission-critical flows like payroll, the best UX often feels invisible, it works so smoothly that users barely notice it. But global payroll is rarely that seamless.
Rather than reinvent the system from scratch, we built on Upwork’s proven payments infrastructure to automate deposits behind the scenes.
This allowed us to deliver speed and reliability without adding unnecessary complexity.
On the design side, we introduced subtle but intentional nudges that prompted clients to set up payments before sending a contract. This ensured funds were ready in advance, so payments could be processed automatically and on time.
The result was a system that felt smooth for users but delivered powerful emotional benefits: clear status updates, predictable timelines, and payment confirmations that reassured both sides. For employees, it reduced anxiety. For clients, it signaled professionalism and reliability.
Answers Before Questions
When users can understand and anticipate what’s happening, trust builds naturally, even in complex systems. During interviews, we found that uncertainty, not difficulty, was often the source of user hesitation, especially when dealing with sensitive tasks like compliance, contracts, or payments.
Transparency became a key strategy in closing this trust gap. Rather than waiting for users to ask questions, we aimed to stay one step ahead, proactively surfacing the answers they didn’t know they needed. Features like cost previews, benefit breakdowns, classification comparisons, and in-context disclosures gave users visibility into what was happening behind the scenes.
This level of clarity helped users feel informed and in control. But more than that, it reduced anxiety and replaced hesitation with confidence, creating an experience that felt less like navigating a legal form and more like getting guided support from a trusted partner.
Protection as a Product Feature
To support non-experts making high-stakes decisions, we shifted the burden of legal and compliance risk away from the user and onto the platform.
In testing, we found that fear of making a wrong decision, especially one with legal consequences, was a major blocker.
Clients didn’t want to become employment law experts, they just wanted to know they were protected.
To address this, I partnered closely with our legal team to bring compliance to the forefront, not as a disclaimer, but as a promise.
We framed our messaging around clear, proactive reassurance, highlighting the platform’s legal coverage as a visible safety net.
The result was a shift in mindset: clients no longer felt like they were navigating risk alone, they felt supported, secure, and confident enough to move forward.
Deliver
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.
(Need a better view? Click the expand icon in the top right, then hit "Z" to zoom it just right.)
The Pivot: A Quiet Launch and a Strategic Shift
In a last-minute pivot, leadership decided to shift away from expanding a payroll solution for external talent, so the AnyHire launch was intentionally low-key.
The focus turned inward, toward enabling full-time employment for freelancers already on the Upwork platform. That strategic shift led to my next project, Full Time, but that’s a story for another day.
At the time of the pivot, around 250 early adopters were actively using Any Hire, most of whom had joined during the testing and pre-launch phases.
