What the jobs report isn't telling you about AI & the workforce, with Upwork’s Hayden Brown

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1:57The future of work is arriving, and it's arriving on our shores right now, right here, whether we want it to or not. The urgency and the need for all of us to become fluent in using AI for our jobs, I mean, that is something none of us can escape. You can't learn to ride a bike in a seminar, and I think the same is true for AI. Until you're using these tools day in and day out, you know, really integrating and pushing what's the boundaries of what they can do. That's when I think people become extremely capable. Will humans win or machines win?

2:29I think that is distracting us from, in some cases, putting, you know, our collective societal energy towards building a future where everyone wins. That's Hayden Brown, CEO of Upwork, the global tech platform for freelance workers. As AI radically resets expectations across the workforce, Upwork has a critical vantage point on how the job market is actually evolving. I wanted to talk to Hayden about the on-the-ground reality beyond government job numbers and the dreamy predictions of AI cheerleaders.

3:05Hayden is forthright about the pressures facing organizations and their teams, including her own decision to lay off Upwork staffers earlier this year. She shares which jobs are most in demand, the good and bad of AI agents, and where she sees the future of work moving. Plus, she talks about the challenges of leading when even a one-year planning horizon is too far, revealing her specific practices for resetting strategy on the fly. So let's get to it. I'm Bob Safian, and this is Rapid Response.

Labor market data and realities

3:44I'm Bob Safian. I'm here with Hayden Brown, President and CEO of Upwork. Hayden, great to see you. Great to see you, Bob. Thanks for having me.

4:15You were last a guest on the show. We were talking geopolitics, Russia, Ukraine. It was pre-Great Resignation, pre-return-to-office controversies, pre-Gaza and Iran. Now, of course, AI anxiety dominates workforce discussions. It's like we've been through decades of change all piled together. How are you doing? I mean, it's been a challenging time to be a CEO. You know, it definitely feels like there's a lot happening. I have a kind of running joke with some friends who've run other companies.

4:47We all say, you know, what's going to be the black swan event of this quarter? Because it just feels like there is so much happening in the ecosystem and things are moving faster and faster. But I think that also is very exciting. It's a dynamic time. I was going to say a black swan every quarter or maybe a black swan every week. Like you sort of don't even you don't even know if it's a black swan until it's already moved on. Right. Exactly. You're on the front lines of changing work habits. And I find myself wondering a lot if sort of traditional assessments capture the realities of the U.S. labor market in 2026.

5:24Like the most recent monthly jobs report showed 23,000 jobs lost. But at the same time, unemployment numbers went down. Also, how do you make sense of this data? How much do you focus on it? Does it reflect what you see on Upwork? Yeah, there are a lot of competing dynamics. It certainly doesn't tell the whole story. We do see kind of consistent with the jobs report data, the labor market is very subdued. It has been for several quarters.

5:54It continues to be sluggish. I would say we particularly hear about kind of macroeconomic and labor slowdown with our very small business customers. You know, those are the guys who are out on the front lines of the economy without a lot of resourcing, without, you know, deep pockets and financial reserves. And I think they're the ones who are feeling quite pinched right now. And what they tell us is they have pulled back hiring across all channels. You guys recently released a future of work index.

6:24Is that what encapsulates this? Are there other things in that index that business news headlines maybe aren't capturing? Yeah. You know, while the picture overall is of this kind of slow-moving market, there are pockets within it that are incredibly vibrant. We really see the growth in AI-related skills, AI-related jobs. That is the place where energy and money is flowing. And we see that in our platform with our own AI category growing over 22% year over year. And just all of the data is telling us that the demand from both small businesses all the way up through large enterprises for talent who really know and can help them navigate this new world of work and bring in these relevant skill sets and knowledge of how to use AI tools, that is really where the energy is going.

7:12And the dynamics are moving from full-time towards fractional work, which is a really fascinating trend. Our most recent survey showed a 10-point increase in freelancing in the U.S. within knowledge workers. It's at 38% of the population today. It was at 28% just a year ago. So there has been a huge step up in both workers moving into the freelance economy for a variety of reasons, but also businesses saying, you know, we want to find these workers who are out there doing contingent work because we don't necessarily need the same number of full-time employees we needed before.

7:45We can approach this work differently. And also, we can't access these folks maybe through kind of full-time employment channels. There's so much talk about AI potentially taking jobs. And there are some layoffs that companies attribute to AI, and yet you have other CEOs claim that AI is allowing them to add staffing because each AI-enabled person is more productive. It sounds like both fit in what you're seeing, but, like, it seems early to know what AI's impact is going to be.

8:17Or is there something clearer that you see through all of this? You know, I think it's 60% of jobs that exist today did not exist in 1940. And I think that's helpful context for us as we look at what's happening with AI. Technology and other forces have, you know, destroyed and created jobs again and again through so many cycles. This is kind of a version of that, but happening just bigger and faster. More destructive on the negatives, but also more creative on the positives.

8:49It's a very binary picture. You know, there's the camp of AI is going to take all the jobs and, you know, humans and the companies, you know, that serve humans and do human solutions are doomed. And then there's the other side. The reality has to be somewhere in the middle. We do not see mass job destruction as the future. There is really, I think, a balance to be struck. And, you know, again, there's creation and destruction, but at the end of the day, it's not all destruction. It actually is a lot of new jobs and roles and businesses that are being born because of this exciting technology.

Staff cuts and AI realities

9:18You announced in May that you had to cut a quarter of Upwork's corporate staff yourselves. You published a pretty frank statement about it, owning the decision. And you talked about AI but didn't blame AI. Why was that necessary? Yeah, I made that decision earlier this year because we really did see that with the market conditions that were changing, this was the right time for us to expand the profitability of the business, which was already part of our long-term goals.

9:51At the same time, Bob, we've seen that because work is changing, our own work needs to change. And what we did for that was not, you know, really just automating and replacing work or workers with AI. Instead, we looked across the entire business and asked ourselves in every team and every department, what would this look like if we really were doing this function from the ground up today using the best technology and tools that are available? We also looked at newer operating organizational models where we could flatten the teams, get more leverage for managers with broader spans of control, fewer layers in the organization.

10:26You know, some of these things that are kind of evergreen opportunities to refine how we operate. I mean, there are contentions, I guess, that some CEOs do AI washing. They ascribe to AI the reason why they have to make changes as opposed to owning that maybe they didn't have the right strategy in the first place. But by blaming it on AI, like, they get credit for that. You know, their stock price goes up. It's like it's a positive. And I wonder whether when, as you were thinking about this, you were like, well, do I lean into that part of the messaging?

11:01Because maybe, you know, that that helps the story. You know, it was so important to me that our messaging around this be really true and authentic. Because, frankly, of course, AI is helping us and it is a contributor to our efficiency and our productivity. But that is not the biggest reason, A, that we made the changes, nor the biggest benefit that we were able to get from kind of driving these changes. So, you know, we're actually seeing the opposite trend in our platform in the sense that the AI washing that you're talking about has been happening.

11:32But also, a lot of folks are now reconsidering and coming back because they're seeing that the humans they let go, actually, they still need. And the AI can't do all of the things that they hoped that it could do. A recent survey we did showed that 23% of our own clients have actually already moved work back to humans from AI or are about to do so. So I think this pendulum, you know, it will keep swinging. When we've actually done testing of clients trying to use agents directly to deliver work products through our platform, the failure rate of agents is incredibly high.

12:05They almost never succeed in delivering even fairly simple tasks from clients end to end. But when you just add a little bit of human expertise and a few back and forth with an expert, suddenly the success rate goes up more than 70%. We have to sharpen our intuition around when to trust AI. And I think increasingly people are realizing, I'm not going to take this at face value. I want to couple that with a valued human expert who can bring a lot more to that equation.

AI agents hiring humans

12:30AI is directly impacting things that happen on your platform. There's been a rise in AI agents posting job ads, machines essentially trying to hire humans. Upwork even has, I think, a specific service for clients to allow agents to access your freelancer database. It could sound a little spooky. Did it feel that way to you when it first started? I mean, it really feels like the future of work is arriving. And it's arriving on our shores right now, right here, whether we want it to or not.

13:03And that was one of the reasons we launched this, what's called the MCP server, but really is a capability to let agents authenticate with Upwork so we know who they are. We know if they're good actors or bad actors. And then based on that authentication, they can go forward, help post jobs, make hires, manage projects, et cetera. Now, we are definitely doing this because this is where the world is going already. It's not something that we just came up with, you know, out of the box. And at the same time, we're seeing a lot of clients who are working inside these AI tools, Claude or ChatGPT, and they're getting stuck.

13:40And they're having a deliverable that didn't meet expectations or they need a human expert to finish it. With our MCP, now they can directly connect to Upwork, share that deliverable with a freelancer immediately, and get the on-demand help they need from a human expert in real time. Which is a huge advantage because now everyone expects everything in real time. You know, everything's moving so fast. AI has changed expectations. And now we too can meet that expectation around truly real-time human support inside of any of these AI tools where people need additional resourcing.

14:11Upwork has its own agent, Uma, that assists users writing job descriptions and prepping interviews and things like that. For a platform conceived to give humans more freedom, there's some irony in using AI to prepare a job application so another AI can review it, right? Are we entering a labor market where, like, the best job applicant is whoever is best at prompting the hiring machine? Or is it more like, I don't know, like online dating apps where, you know, algorithms are better at matching us than we are on our own?

14:48I mean, these are the big questions. And they're the right ones because we are seeing, you know, spam job proposals and applications. We really just want to put people's own interests and needs on steroids and then have that expressed through the hiring process and the recruitment process that we're supporting them with, including filtering out all of the AI kind of slop and noise that is creeping in now that these tools are so widespread. Right. I guess because if I'm a job applicant, I guess I can create a lot of different versions of my application to a lot of different jobs that may or may not be right for me and I may not even know what I'm doing.

15:24And I guess the same thing can happen on the other side about posting for jobs where if we can find a needle in a haystack, we'll do it. But otherwise, we're just sort of testing the water. Yeah. And I think that's one of the main values that we see being so enduring, even in the AI era for Upwork specifically and our customers, is, you know, the problem we've always solved for them is giving them real, tangible, accurate data around who can do what. It's real data from our platform observing people doing work and delivering for customers with dollars attached.

15:56So this is the most verified work history data really in the world. And it's at scale across, you know, 18 million freelancers that were active in the last year. This type of data is what then gives customers confidence in making that hire, not noise that was created by, you know, an AI agent applying for them, not these empty promises or claims about their expertise. It's actually stripping us back to, like, what does the data say in terms of who's good at what? And frankly, advancing this meritocratic idea of it shouldn't be about who has the best agent or who sounds the most shiny on paper, but really who has the data and the experience to demonstrate that they can do the work that's required.

16:34That in the trenches data Hayden cites illustrates how human-in-the-loop is actually unfolding in an AI world. 23% of businesses moving work back to humans from AI. So how does Upwork engage with the big AI companies, including open source players in China? And what does it mean that freelancers with AI skills earn 34% more? We'll talk about that and more after the break. Stay with us.

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17:36Hey listeners, Bob here. If you listen to Rapid Response on Masters of Scale, you may be missing half the show. Because every Friday, we release a second Rapid Response exclusively in the Rapid Response feed. The guests and topics are just as compelling and timely, from Ford's CEO to NASA's administrator to the lessons from the Devil Wears Prada. It takes about 10 seconds to find. Just search Rapid Response wherever you listen to podcasts, and hit follow to make sure you never miss an episode.

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18:14Humans will never be more intelligent than AI. There's going to be two types of companies. Those are great at AI, and those that went out of business because they weren't. How do we build a future that is human-centered? I'm Rana Elkayubi, and on my podcast, Pioneers of AI, we answer that question and so many more. As an AI scientist, entrepreneur, and investor, I know what it takes to build AI that works for everyone. Every week, I sit down with the pioneers shaping our future, and we take you behind the scenes of the AI that's transforming our lives.

18:52Find Pioneers of AI wherever you tune in.

18:57Before the break, Upwork's Hayden Brown talked about what's really going on in the job market as AI shifts expectations and needs. Now, she talks about dealing with the big AI companies, how to actually build AI skills effectively, and what Hayden calls her crystal ball. Plus, her specific strategies for leading in a world where, as she puts it, even a one-year planning horizon is too far out.

Engaging with major AI models

19:23Let's jump back in. Do you have a philosophy about how you engage with the big AI players? You know, we're at a moment where everything is in flux. We have this growth of these new channels where customers are suddenly doing work inside of ChatGPT and Claude and all of these third-party tools. That is now a new origination point for businesses like ours to be referenced, to be advertising, to be showing up. We also know with 900-plus million users on ChatGPT, you know, Anthropic growing so massively, you know, quarter by quarter, I think we can see that these are the new destinations for work.

20:03The momentum there is building and snowballing in such a way that I think we've taken the approach of building for these tools and this future that we see already appearing, even though there is going to be some ongoing volatility as things kind of mature and play out. Do you have a differentiation between places like OpenAI and Anthropic versus, like, the open models from China? I mean, you do have a global business. Like, do you let agents built on those models be on Upwork? Do you have to, like, treat them differently?

20:34You know, we, you know, look at everything in our authentication layer and do make some judgments about, you know, who is allowed and not allowed to operate in our ecosystem. And certainly those rules will continue to change, you know, as new information is available about safety, security, and other aspects of what these actors can do. So I think, you know, our approach today is to create the system, the framework, and the controls. Our customers really have told us they want to be using these things. They want to benefit on both sides, but they need to do so in a place that's not the wild, wild west.

21:06I ask because, you know, some CEOs I've talked to recently have been talking about how, you know, some of the models from China, they're just so much cheaper. They are. And even though they're not maybe quite as robust, they're robust enough. Absolutely. And I think a lot of those open source models can be used safely and securely with the right controls. It's not a binary of, you know, use Claude or, you know, good luck to you and there's nothing, you know, you can do. So we personally in our business have taken a gateway approach where we are constantly testing, you know, the performance of a variety of different models, including open source models.

21:44And now that token costs have been going up so significantly from the major providers here in the U.S., there are definitely use cases where we know we can get, you know, 10x savings or more by using open source models and doing it safely inside of our own environments. I think this is also a place where for us as a marketplace, creating more of the ecosystem where people can see the pros, the cons, and the costs of different combinations of AI models or agents with or without human supervision.

22:14This is a fascinating extension of our own business because we've always provided customers with the value of choice and selection across a huge supplier base to get something done. And they get to choose, do I want to pay more for speed and quality or am I happy to go a little bit slower and maybe have some savings? You know, these are the decisions businesses always need to make. And now with these AI tools, now they can kind of get the best of both worlds.

The rise of freelance careers

22:37Your emphasis on freelance work and fractional work, as you talk about, like there's been a sort of romantic sentiment behind it, you know, the promise of freedom and making your own schedule. In today's economy, how much of that is a choice versus a necessity, a sort of a symptom in some ways of companies shifting risk onto individuals? Absolutely both. 58% of current full-time employees are actually thinking about becoming freelancers for a lot of the reasons you mentioned around choice and control and deciding when, where, and for who they work.

23:15We also hear really loud and clear from freelancers that the economics of freelancing have become much more appealing over the last few years. Before the 2008-2009 Great Recession, people at that time, I think, felt they were very secure in a full-time job. And then that recession happened and they realized, wait a minute, I'm actually more secure. If I have a portfolio of three to five clients on Upwork, they keep coming back to me for repeat work. Maybe I'm also doing a podcast or a book or a creator economy thing on the side.

23:48And we really have seen this trend towards these portfolio careers. Gen Z is the biggest one. 42% of Gen Z are freelancing. It's actually them saying, look, I feel more comfortable that I'm not exposed and that I can really both learn and use and build the skills I want and also have income that is predictable and in my control versus at the whim of an employer. It's just a different conception of what a career is for younger folks, right? Absolutely. And it also reflects, you know, if you think about this AI moment when everyone is trying to prove that they have these skills or if they don't learn them and then prove like, hey, I've gotten these skills now.

24:27I am an AI-relevant employee or worker. Freelancing is an amazing way to do that because they're getting on-the-job experience, doing real work, proving their skills. And if they're on a platform like ours, that comes with a verified work history, all of the marketing kind of around that that freelancers can do to say, hey, now I can earn more and do more. And we do see them earning more. Freelancers that have AI skills are earning 34% more hour than folks who don't have AI skills. And I think that wage gap really speaks to the urgency and the demand from talent to move into a career where maybe in their full-time job, they don't have the opportunity to use these tools or they're not learning them inside of their employer.

25:06But here on our platform, they can really demonstrate and flex their muscles around AI and get paid for it. Hmm. There's a lot of burden on the individual to keep upgrading those skills as you go. I mean, when software can learn skills way more quickly than humans can, which is what we're seeing with AI, then it does put more pressure on humans. I guess whether you're in a freelance economy or anywhere, to keep upgrading your own skills or refining your own skills.

25:36That is the reality. The urgency and the need for all of us, I mean, you, me, all of us, to become, you know, fluent in using AI for our jobs. I mean, that is something none of us can escape. But what we do see is that freelancers, because this actually pays them and puts food on their table, they do it faster. They learn faster. They lean in harder. They move much more quickly to where the new technology is and learning its capabilities and applying those capabilities in real work settings. We see this huge advantage, actually, with the freelance talent pool that's well ahead of full-time employee counterparts in terms of their adoption and facility with AI.

26:13And that's another reason why businesses are turning more and more to the freelance economy, because they're looking in-house and they're realizing, you know, my team doesn't have these skills and it's going to cost a lot of time and money to try to get my team up a learning curve. Maybe I can short-circuit that by bringing in freelancers who can both add value and do work, but also upskill my team at the same time as a byproduct of sitting side-by-side with them. And so there's a lot of that. So it becomes a backdoor way to train my own team at the same time. Exactly. And not have to wait for those, you know, fruits to materialize before you start to actually see some real business benefit.

26:46Because a freelancer can be adding value in hours. Yeah, I mean, well, that is one of the big questions, you know, all of us have is like, how long does it take? What's the best way to train people in the AI skills? I was actually talking to one of our clients this morning and he said, you can't learn to ride a bike in a seminar. And I think the same is true for AI. You know, you could watch a YouTube tutorial and get more familiar. But at the end of the day, until you're using these tools day in and day out, you know, really integrating and pushing what's the boundaries of what they can do?

27:18What are the limitations? Why is that? How do I work around that? You know, that's when I think people become extremely capable. And that's one reason we're seeing the rise of a new generalist called the AI orchestrator. This is becoming extremely popular on our platform because people are looking for someone who can orchestrate and use these AI tools, but also is not necessarily so deep in one domain. Instead, they have the facility to evolve, adopt new tools, figure them out very quickly because we know the technology is moving so quickly.

27:49In what you do as a CEO, how are you using AI?

Internal AI use and leadership

27:54I think AI, obviously, some of its core skills are like data gathering generation and synthesis. And so inside of our environment, we've set up a very powerful tool. We call it Crystal Ball, and it has access to all of our internal data. And this is wonderful for me because instead of having to go ask someone on my team, like, hey, send me the most recent report on this or like, you know, what happened on this day with this customer type? I can actually just directly query our database just through natural language, get tons of insights around real-time business information, which then we are using in real time to make different decisions.

28:29As I alluded to it at the beginning, you've been CEO through this extraordinary period, you know, pandemic, Ukraine invasion, which prompted you to shut down operations in Russia and Belarus, a backlash against globalization, which also kind of threatens Upwork's premise. One CEO talked to me a while back about building a cadence of change inside his organization to, you know, keep it agile. But now the cadence of change is like coming from outside. And I wonder how that impacts how you make decisions, how you know what to focus on.

29:03We've worked to try to, like, remove noise in the organization so that it's very clear the small number of things that we're working on. And then if we need to change one of them, that we can communicate that really clearly once that decision is made. Because I think, you know, the more cruft there is in the organization around competing priorities and people moving in different directions, that just makes navigating through these types of environments even harder because it's so unstable externally that you need to have, like, full, locked-down stability and focus internally. We've also changed our planning horizons. I'd say, you know, in the past, you know, I was a product manager for many years before becoming a CEO.

29:39And, you know, you would have, like, a one-year roadmap. And, yeah, like, it would change and everything else. But it didn't feel unreasonable to have some idea of what you want to be doing for a full year. Now, in product, if you have a one-year roadmap and really you're executing the same thing in month 11 that you thought you would be, you know, when you started, something's probably wrong because you will have learned so much more and the technology will become more capable. So we've shortened some of our planning cycles, still setting kind of big, ambitious goals out in the future, but not being as committal to, you know, the steps required to get there.

30:11It's kind of like, let's take the first step and then reevaluate what is that second step. Let's not presume that from this vantage point today we know what that is. And when you're trying to focus and prioritize, like, do you have tools that you use to do that? I mean, I remember talking to Daniel Eck at Spotify at one point and he would say each quarter he'd, like, create a list of 10 things, but they were ranked. Like, you couldn't go to number two until you satisfied number one. We use ranked lists all the time, like Daniel.

30:41I think that's a really important one. We also look at kind of what is our portfolio, how much resource we're putting in for things that we have a really high confidence we'll deliver in the near to medium term because it's a road we've gone down before and we know it well. Versus where are we putting resourcing in for things that are much more speculative or building for future states that we anticipate or can kind of see coming but may not have arrived yet. And I think it's become even more important in this environment to be very clear and have internal alignment around how much of each of those activities you're doing.

31:13And also when you make changes, again, maybe something that was out in the future six months later, now it's here, it's arrived today. You know, it has to move into the other part of the portfolio and then you've got to be thinking, okay, where are we investing in that next, next horizon once now that we've, you know, accomplished the thing that was out there in front of us. What's at stake for the future of work right now? The binary debate that's happening around, you know, will humans win or machines win, I think that is distracting us from, in some cases, putting, you know, our collective societal energy towards building a future where everyone wins.

31:48Where humans win with AI and empowered by AI, but not at the loss, you know, of jobs, opportunities, and purpose that people, you know, have and will, I think, always need from doing meaningful work. Well, Hayden, this was great. Thanks so much for doing it. Thank you so much. Great to see you.

32:09There's so many rich insights in Hayden's comments about how to lead in changing environments, about the good and bad of AI agents, about how to build skills today, and Gen Z's changing perspective on work and careers. I keep coming back to her reflection on meritocracy, that Upwork's system quantifies and captures what specific human talent actually gets done and the value delivered. When it comes to how AI will change the future of work, so much of the data is essentially guesswork.

32:40Of course, gazing into the future has always entailed a bunch of guesswork. Whatever crystal ball Upwork has built internally, it only reflects the past. But what we do know is that what's valuable to humans can only be determined by humans. Appreciating what we each do and how we do it, that's something that will always stand the test of time. I'm Bob Safian. Thanks for listening. Rapid Response is a Wait What original.

33:18I'm Bob Safian. Our executive producer is Eve Trow. Our senior producer is Alex Morris, and our associate producer is Masha Makutonina. Mixing and mastering by Aaron Bastinelli and Brian Pugh. Our theme music is by Ryan Holiday. Our head of podcasts is Leetal Malad. For more, visit RapidResponseShow.com.