In Upwork’s future of work, everyone’s a CEO and nobody works full time

Upwork CEO Hayden Brown on the rise of the freelancer, the problem with the term “freelancer” and the post-pandemic work trends that will change your office forever.

Portrait of Hayden Brown, Upwork's CEO, on a white background.

Hayden Brown has been Upwork's CEO since early 2020. A lot has changed since then.

Photo: Upwork

Anyone who tells you they know what the future of work looks like is lying to you. For some people, post-pandemic work looks completely different than it once did, while others are already back in the office in roughly the same way as before. But there are big trends, even bigger than the pandemic, around remote work, flexibility, corporate values and work-life balance, that are disrupting all facets of the workplace.

Hayden Brown, the CEO of freelancing platform Upwork, is definitely biased toward a freelance-first, gig-based version of the future of work. But she’s also had a front-row seat to a huge amount of change, after becoming CEO of the company only a few weeks before the pandemic hit. Since then, she’s had to help employers and workers alike navigate new ways of finding work and new ways of getting things done. And while she admits freelancing isn’t for everyone, she’s also confident that neither is a full-time job.

Brown joined the Source Code podcast to discuss Upwork’s recent rebrand and its efforts to describe and understand the future of work. She also talked about how a push for flexibility is changing workplaces everywhere, why the freelance economy is so appealing to so many people and what companies can do to catch up.

You can hear our full conversation on the latest episode of the Source Code podcast, or by clicking on the player above. Below are excerpts from our conversation, edited for length and clarity.

I want to talk about this big rebrand you went through. Because we’re in this weird time where everything is changing, nobody knows anything about the future of work, everything's very complicated. And it seems like you guys saw that as a moment to be like, OK, let's try and name some things, explain this world a little differently and figure out our place in it. What does that process look like at a place like Upwork? When you decide, “We’re going to rebrand,” what happens?

The starting place for us was the realization I had that no one understood what was happening on Upwork, or what this category was. I think that was really the genesis of the rebrand. People thought Upwork was freelancing, and people have very specific ideas about what freelancing is and means and can do for their businesses and talent. They have really specific ideas about whether freelancing is or isn't for them. And I think those ideas are very old-fashioned and outdated, for both clients and talent.

We had this lightbulb moment last year where it was like, Upwork is so much more than freelancing. And we need to define for the world what this is and what's happening here in our marketplace that's not just freelancing. And so we went through this journey of discovery: We talked to tons of customers, we did a bunch of research to figure out what is really happening here, what is the value we're creating for customers. What do we call this thing? And we came up on the other side of that research with the insight that this is really a work marketplace we're building. It's not a talent marketplace, because that implies clients shopping for talent, and that's commodifying the talent, which is not what we're about. And it's not something just for talent, either. It's a two-sided marketplace, where both sides are getting value, where work is really getting done in new and innovative ways. And so we concluded that, really, it's the work marketplace, and that we needed to put a name around this category that was not well understood in the world.

Part of the reason I'm so interested in the rebrand is that for forever, the two kinds of work were basically full-time work, which had a very specific meaning, and then freelance work, which also conjures an equally specific picture in your head of what that looks like. And the last 18 months have just broken all of that. Now it seems like there are a million new things in the middle. How do you even think about that now? Is work just this teeming mass of possibilities now? How do you map that out in your head?

This is my favorite subject. We are at this moment of absolute tectonic change. I think we're going to look back on what's happened through the pandemic as this very bright line — the before — and now we are starting to be in the after. And I think we're seeing people really waking up to the fact that work can look so different than what it was before.

On the talent side, there's been an explosion of career innovation, and people are starting to realize they can innovate their careers to be so many different things. We're seeing people do things like, “Wait a minute, I can work two full-time jobs at the same time?” We've seen through the research on our platform, 2 million incremental freelancers joined that economy in 2020. Now 10 million more Americans have said in our surveys that they are thinking about joining freelance right now, because of the flexibility it gives them. And that is just exploding.

People are just realizing the values that they have in terms of their work, their life, what they get from work, are very different than what they thought before the pandemic. And I think the things that for professionals were tolerable before, or were invisible to them before, in terms of the price they were paying to do certain types of jobs — whether it was a commute, or they didn't like not seeing their kids — all of those things that they were putting up with before or didn't even notice, have suddenly become intolerable. The invisible prices they were paying have suddenly become totally visible, and they can't imagine actually living with them after this.

People are just realizing the values that they have in terms of their work ... are very different than what they thought before the pandemic.

And then on the business side, the second big trend is businesses realizing that they cannot find the talent that they need through the old channels that they were using. The talent sourcing of FTEs (full-time employees) and that model is just breaking for them. You see that with the Great Resignation stuff: They're finding that the old work models are too stiff and brittle in terms of moving fast enough in an ecosystem that is calling upon them to move faster than ever. So now the companies are saying, “How do I keep up with the fact that talent is demanding new and different things, my business model is requiring me to move faster and have more agility, and I need to innovate how I'm working in fundamentally different ways?” And those things are converging to create this kind of cyclone effect of work innovation in terms of the practices and everything really changing dramatically.

Obviously, a lot of these things are like trends that have moved really quickly in your direction during the pandemic. But are there things that have gone differently from where you were, or that have changed your perspective on things? Does Upwork the platform have to be something different now than maybe it would have been if some of these trends had come more slowly over time?

I think what we're focused on is continuing to educate the market about what this work marketplace can really do for customers. I get the question a lot: What happens post-COVID? And I think, as much as we benefited from this COVID-related tailwind of people discovering remote workers on our platform they could suddenly tap into at scale, there is something like 90-plus percent of the addressable market who has never even heard of Upwork, or doesn't know us. The demand side of our business is just still so nascent. And despite being the market leader in our space, unaided awareness is a huge challenge for us.

We aren’t Zoom, it's not like everyone woke up during the pandemic, and said, “Oh, now I'm going to source all my talent through Upwork.” There was definitely an increase in awareness! But the metaphysical barrier for us is still giant, in terms of people just not being aware of us, and generally what the category can do for their businesses. There's so many misperceptions out there, the stigmas around what independent talent can do for businesses.

So I think for us, it's growing beyond those stigmas, breaking down those barriers and really reaching out to that other 90% of the market that doesn't know about us or think about us in the right ways.

Zoom is an interesting example. At first, everybody's like, “I need to have meetings.” And so we just found Zoom. Now, it's like, OK, but what if we thought about what work looks like if we didn't have so many meetings? And now we're starting down this road of much bigger, more interesting questions about how people work. And it seems like the questions about how talent works and how companies are put together is lagging behind that, but going to go down that same road. OK, how do I find good people when everybody's quitting their jobs? And then the question gets more nuanced and more complicated: How do I rethink the way that my company actually operates?

It’s a perfect analogy, because what's been surprising to me is the preoccupation still being about where the work is happening, almost two years into this. We need to move past where, to who and how, and I think that's starting to happen.

That's where the real unlock is for businesses, when they start to get past this whole obsession with where the work is, and start to figure out that once they are past that, they can tap into talent that really does serve their needs, and answer the question that they had before the pandemic: Where do I get the next great talented X? Or how do I fill this gap in my organization?

One easy criticism to level at something like Upwork would be that you're fighting against the idea of full-time employment, and you're like, “Everybody should be freelancers! Forget having a job, come do it here, it's better and cooler!” All the things people say about gig-economy and ride-hailing stuff that falls apart as soon as you start thinking about it. But my sense is that you don't necessarily see those two things at odds in the same way.

They're really not zero-sum. When you talk to the talent on the platform, here are the things you hear. Number one, “I'm doing this because I'm actually earning more than I was earning, doing whatever I was doing before.” And that's increasingly the story: People are able to command incredible rates for their work. The second thing you hear is people doing this because it's the thing they love. And so often, they were working a traditional full-time job as a graphic designer, or whatever corporate job they were doing before. They love doing that work, but they were doing much more politics and meetings and managing up and managing down. And so a lot of the folks on our platform are delighted, because now they're just doing the illustration, doing the graphic design. They’re not doing all the other stuff. And we take care of all the business management tasks for them.

The other thing you hear is just the freedom and flexibility, which is obviously something that so many workers have woken up to their desires for through the pandemic. Historically, freelancers have always been able to carve their schedule to be exactly what they want. They're able to define those parameters in their career to exactly meet their needs. And so these are extremely empowered professionals who are entrepreneurs, building their businesses, doing it on their terms. And I think that is really empowering and liberating for them.

How broadly applicable do you think that model is to everybody? The graphic designer is the perfect example, and a pretty easy one to imagine how a job and structure like the one you're describing works. But is Upwork a place for accountants or middle managers? Does this work for every kind of job in every kind of industry?

That's the beauty of the liquidity of a marketplace like ours: Once you start to build a system like this at scale, you realize how many niche skills even there's demand for in the world, and how someone can actually build a career doing these things.

You give the accounting example. How many FP&A teams right now are going through the budgeting process for their companies, and are wishing they had somebody who was on their virtual talent bench who knew their company, already knew their systems and was part of their team? And by the way, that's a process that they need every quarter.

When you start to peel apart the layers of work, there's this bad habit that corporate America has of thinking every unit of work is an FTE unit, or a guest TE unit. “Hey, I have some work, I better hire someone to do that.” And that's kind of the lazy person's way of estimating the workload, when in fact there's actually a much more sophisticated way to think about it and to parse that work out to a team or an individual freelancer who can actually augment and be super successful.

Flexibility has been a key thing for freelancers forever, right? But now all these companies are starting to embrace more-flexible work, and they're bending over backwards to try and retain employees. What are the new appeals of freelancing that you're finding as the platform is growing? Are people coming for different reasons than maybe they did a few years ago?

They're coming for a lot of the same reasons, I think those reasons have just become more top of mind. For example, half of Gen Z is freelancing today, and I think that's just growing in popularity, because people are realizing that the modern career path doesn't necessarily start in the large corporation and end in the large corporation.

What used to seem like the safe path of going the employee route, now actually doesn't necessarily look so safe anymore.

And, frankly, what used to seem like the safe path of going the employee route, now actually doesn't necessarily look so safe anymore. With layoffs in 2008, and going through the pandemic and seeing so many companies lay off, people are saying, “Am I actually more exposed if I just have one employer who might or might not lay me off? Or am I more safe building a career where I have a bench of folks I'm earning from, and if one of them goes under or pulls a project, I've got my whole business going?” When they look at that comparison today, I think they draw very different conclusions about which is the more safe and secure path for them.

I spend most of my time talking to people in tech, at deliberately innovative companies who went into remote work really fast, and are thinking big, deep thoughts about how things get done. They're trying new tools, they're trying new systems. But most companies and people do not operate like that. And so one of the things that's going to be interesting to see over the next few years is whether this keeps accelerating, particularly globally, or if there is a retrenchment period where people are like, “Oh, thank God, we can just go back to the office,” I do think the arc of the future bends toward the kind of stuff you're talking about, but I am curious sort of how straight a line it turns out to be.

I think the interesting thing there is, you actually don't need all of the industry players to be succeeding at this all at once. You really only need one or two winners in each industry before the entire industry basically faces a choice, right? Follow the leader, or fall behind. And that's what we see in our business: When we make inroads with a certain business in one space, they start using freelance talent at scale and programmatically. Up until that moment, most of the industry is not paying attention to what's going on with freelancing and Upwork. Once one of these industry leaders is actually doing this and realizing huge velocity, huge talent access, cost savings, flexibility, whatever it is, all of a sudden, everybody's looking around like, wait a minute, how are they doing that? How do I get it? How do I take advantage of that? I better get on that bandwagon.

It's not like all of the companies in packaged goods or logistics or ecommerce need to be winning at distributed remote work. All it takes is one Amazon who figures it out, and then the entire industry is like, “If we don't figure this out, we're gonna get totally lapped.” And you think about the Amazon example of how much they pioneered so much of day-one thinking and innovation and all these concepts that now trickle down to so many other players in their space and other spaces. I think there's a similar effect that we'll see here, with the companies that truly take advantage of the power of working differently with remote work, distributed teams, etc.

It could only be a handful of them, but they will be so successful and disproportionately effective at what they're doing and how they're doing it, that suddenly, all eyes will be on them. And everyone will be racing to catch up.


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