Name: From Static to Fluid: Rethinking Where and How Work Happens
Uploaded: 2026-05-20
Duration: 18 min 18 s

The 9-to-5 in a dedicated office is no longer the default—and neither is the full-time employee. As AI reshapes workflows and hybrid trends become more prevalent, companies are treating both physical workspace and workforce composition as strategic levers. Two CEOs at the center of this shift—one reimagining where work happens, one redefining who does it—share how they are shaping workplaces and teams to help businesses stay agile and competitive.

Hayden Brown, President and CEO, Upwork
John Santora, Chief Executive Officer, WeWork
Moderator: Phil Wahba, Senior Writer, Fortune; Co-Chair, Fortune Workplace Innovation Summit

From Static to Fluid: Rethinking Where and How Work Happens

Conferences

Um, so many changes affecting the workplace at the moment. Um, AI, of course, lots of layoffs we're seeing aging population, uh, immigration limits, um, entitlement programs, um, lots going on. So, um, from your respective seats, what is affecting, what is changing your business the most at the moment of, of all these trends reshaping the workplace? So Hayden, why don't we start with you. Sure, uh, thanks for having me. We at Upwork are really in the center of the AI storm right now, so that's, you know, the biggest trend. It's impacting both what talent businesses are looking for in our platform. Uh, small businesses are really looking for us to be the AI diffusion layer that gives them access to AI talent they need. It impacts our enterprise customers who are looking for AI power solutions from us in terms of deploying contingent, uh, workers at scale, and it impacts us as a tech company because we're not only building AI tools, we're also adopting them internally and changing our own workforce as a result so that. Feels like it's really hitting every layer of our business right now in a very exciting way, but also, you know, creating a lot of new questions to answer. And over at WeWork, so we're seeing some real significant growth across the boards, um, in all our offices and in all levels of, of occupancy. Real estate is becoming more of a. The, the flex world is becoming more of a critical component and long term structural shift in how real estate is held, right? The, the, the, the investments in 10 year leases, 15-year leases with lots of capital, we've given the flex world has given the ability for companies to balance that out and not always be in that. And then we're seeing tremendous growth from the AI sector. And from all the startups, so we have 220 AI firms in our spaces today. Lots of them are startups. We have the biggest, but we have all the startups, and, and we just see continued growth in that entrepreneurial business across the board. So it's an exciting time. So a greater percentage of the labor force right now is on contract or part-time. Um, Will that be a permanent change and how does that affect your respective plans? So Hayden, how about we start with you? Yeah, this is, this is a permanent fixture of the workforce. Uh, the percentage of workers who are in the freelance economy or the contingent economy has continued to grow every single year for probably the decade plus that we've been doing an annual study on that, and the reasons for that are several. One of the things that's very unique right now is. Freellancers are increasingly choosing to work at the flexible model because it gives them actually more economic security. It insulates them from some of the, uh, uncertainty and volatility in the market, and that's a reason why when you actually talk to Gen Z. 83% of Gen Z say working a freelance career is actually more valuable than a traditional job, and 53% of Gen Z are actively freelancing. So we are seeing, I would say, at every successive generation, more and more participation in contingent of freelance work and a greater recognition that this is what gives people kind of the freedom, the flexibility, and empowerment to run their career on their own terms. And does that attract more people who might want a space at a WeWork? I think it, I think it absolutely does, and I think the So we say that the workplace is becoming more flexible but more accountable, right? So when I look at my, our direct workforce, so I say you need to be in 3 or 4 days a week in the office and then the 5th day you can be from anywhere, but life gets in the way. Right, there's childcare, there's parental care. You've got to go to a doctor. When was the last time anybody could see a doctor on a Saturday, right, or a dentist or, or get your car fixed. All life gets in the way. You have to give people that flexibility, and if you don't, they're going to migrate to some other company or some other way of working. And we continue to see the freelancers, we actually had two. Jobs last week that people decided they originally accepted and then decided no I kind of like this flexibility of free freelancing um so so yeah it's a different that's the old contract like I had where I spent 47 years at Cushman and Wakefield and you progress up. That's no longer here, that's long gone. But the commitment from both sides isn't the same, and I think as companies stopped with pensions and all kinds of benefits, the employees said, well then why do I need to go through this? Well, I'm gonna move for more salary, more flexibility, more optionality. I wanted to go back to AI because it's probably been what, 3 minutes since it was mentioned, but um. Uh, just in the last few weeks, you know, we see headlines, this CEO or that CEO, they're usually in tech, say, oh, AI is going to briefly lead to 20-30% unemployment, and then we're going to figure it out and it'll all be rosy. Now, of course, if you've studied history and have a bit of humanities, you know that 30% unemployment is a recipe for a lot of things that would not be good for business. So Uh, at all, it just seems sometimes that a little HQ is lacking over there, but anyway, um, what can companies do to reassure workers that AI is not going to lead to this massacre and help them get the training they need to adapt to it and maybe sort of change this. I mean, I'm, I'm actually amazed that they think say things like that, uh, are constructive, but, uh. Yeah, I mean the hype is real and I think the fear mongering is a real challenge because it does create a lot of this, not just uncertainty, but I think employees are really wondering what their place is, you know, are they gonna have a future, etc. But the data is actually very different. So yes, we do see some companies doing layoffs, and I, I call it AI washing those layoffs, saying like, oh, it's AI, we're getting all these AI benefits. Quite often I think it's just plain, you know, tightening belts and responding to a volatile economy in a time where companies need to be more lean. But at the same time we actually have done some studies on our own platform where um we've measured what can AI agents do alone, what can they do with humans, and what can humans do alone, and even for the smallest, simplest tasks, think of things that can be done for a couple $100 we see that agents complete those tasks 70% better if they have human oversight. And that really is, I think, just one indication of the fact that this technology is very powerful, but it still needs human intervention to be usable and useful. We're also seeing some really interesting trends where for the first time in 2025 we heard our client side on our platform saying, you know. I used to hire for the most technical person or the person with the deepest domain experience. Now I actually want to hire for someone who has judgment, creativity, problem solving, someone who can move and learn at the pace that technology is moving at. And I think both of these things are good signs that there are robust and growing roles for people. We see AI skills growing more than 40% year over year in our business. Some of them are up 200% plus. There's new demand out there. It's just that the demand looks different and the roles are changing. And so I think the fear mongering around job losses and all of that is, um, a factor, but it doesn't actually, it's not actually supported in a lot of the data that shows jobs are growing in a lot of areas. The work is changing, and for people who can adapt, um, there's gonna be a lot of opportunity for them. Yeah, there's no, there's no question that the. The entry level higher is under pressure, right? And, and, and the young talent coming out of schools they're challenged by AI can do the research, AI can do some of the basic tasks, but it's incumbent upon all of us to bring that talent in and to educate the talent and, and teach them to be the future growth of all our organizations. Um, AI is not going to provide empathy and leadership and mentoring and all those skills that you need to lead a company for a company to be successful. So I do think there's clearly an over rotation on the layoffs on the holding back on hires, but I think it ultimately balances out. We go through these cycles and have and, and, and every time there's a new technology change or an industry. Uh, change, so, um, I think it, I think it does balance out. I think companies become more productive, which means they make more money and they grow and they hire more people, but this is a tough time to be in that middle that as we, as it, as it balances out. And if more workers are freelance and unattached, how do they get the training that they need to stay relevant? Well, an amazing reality of the freelance economy is freelancers are intrinsically motivated to self-skill and upskill much faster than in-house employees, and we see this in the data. Uh, freelancers typically have been adopting AI tools at a faster rate. They're more confident with those tools, and it makes sense because they've gotta have those skills to put food on the table, whereas employees, you know, have a different calculus in terms of what needs to get done every day. So we actually see large and small businesses turning more to the freelance economy right now because they do need the people with those AI native skills with those capabilities and often it they don't have them in-house, uh, training people to get there is an option, but that can be slow and expensive and so they're really looking at redesigning. In their workforce to have a bigger portion of the workforce be flexible and contingent so they can access on demand skills, uh, spin up and down new projects at the pace they need to, and, and relatively to that shrinking their full-time employee base just because the benefits of having a larger contingent workforce are become even more apparent. I couldn't, I couldn't agree more with you. Um, the other thing is. We as leaders need to give them those tools. We need to train. We need to bring them on board. We need to, you know, for, for us in our world, we did 52,000 networking events last year in our spaces. Those events help from an education standpoint but also help them meet the people they can learn from, learn with, and grow with, so. Uh, I, I, I think the world has changed, that, that the freelancer is such an important part of our world and will be going forward. Of course you know that does beg the question about benefits. I think millions of Americans stay in their jobs for their health insurance and not because they love the job, so I, I wonder if that doesn't affect um. If there was, you know, healthcare that was more affordable for freelance workers if we see more freelance workers, but, uh, I don't know what, what, what do you think impedes more people from choosing that route? Yeah, I mean how sad is it to stay in a job you hate just to get the health care that you need, you know, we don't want that as a society. Um, the good news is on our platform we see freelancers actually earning more and more and actually earning a premium to what they were their, uh, full time jobs if they were doing a full time job before because they're able to really monetize these highly valuable skills. AI skills are commanding a 40% premium in the market on our platform. Uh, and that's just one indication of how I think people can really create economic conditions that let them, if they need to pay for healthcare, other things, of course, do that, uh, and have the lifestyle they want while also maintaining flexibility and freedom, which is so important to people. So one thing that I guess is self interested I'm fascinated by is is how much later we're all gonna work because who knows if there's Social Security waiting for us um uh so longevity is uh there's we're all living longer hopefully that means better as well but. What will this look like, um, in a few years? Are we going to start to see a lot more people not go from 40 hours a week to zero and then sort of when they get to their mid-60s to a few years? Of, of working like what does this, where are we going when you factor in, uh, social programs but also the benefits and, and demographics and, uh, longevity where do you think we're going? I, I see and we see in our spaces that the, the reinvention of the, the 60 year old, the 65 year old, they're, they're becoming consultants, they're out there working, they're, they're helping to train talent, I think. It's, it's, it's actually wonderful to see now. I took on a second career. I mean, I spent my entire career at Cushman-Wakefield for 47 years, and I said I'm gonna do this, this is something different, and I was ready to hang it up, but it's one we're healthier, longer, right? We want to work, we wanna. Minds to go and they have something to give back and I love seeing that. I'll see a, you know, a 60 something year old and, and then a bunch of young talents in the same office in room and it's like this is really cool. It's a great, great next step or or last phase of work. Yeah, and I add to that, you know, this idea that we do all this learning, you know, through college and in our early twenties and then it's about just being employees or workers after that is, is totally not true anymore. Instead it's all about like lifeline, lifetime learning, reinvention on the job, learning from the work you're doing, and we see that a lot in our platform where when we talk to freelancers, one of the top reasons they say they love freelancing is because they're constantly able to move into new places, try new things, work with different clients, and that becomes this continuous kind of refreshment and learning opportunity for them, which is very dynamic. I think that's gonna become more predominant. We really see this side hustle becoming the main event for. So many folks as they, whether they're Gen Z and they're seeing that they can have this portfolio career or whether they are tired of doing, you know, the thing they've done for so many years and they want more freedom and flexibility to freelance on their own, there's so many reasons why I think people have more options now and that's amazing at a time when, you know, it can feel scary. Instead, actually people have a lot more options for how they can earn and how they can learn through, uh, these types of freelance jobs. They also bring those soft skills that are really needed, right? And, and that's the part that's missing, um, the ability to train, to lead, the empathy and, and that's, that's something that the older generation has that, that needs to be taught. Yeah, a couple of years ago I interviewed, uh, the former, now, uh, CEO of AARP, and the discussion was job shortage, and she said, old people, why don't the companies get it? Hire old people, we're reliable and we work hard, and anyway, I guess, you know, we're, we're, um, and it's as I 65 gets closer and closer every day, it's like it's not that old after all, you know. No, it's a new 45 and when you were 2065 was like, oh, they're fossils, but anyway. Uh, perspective changes, um. Do you think we're ever gonna get to an era where um. Even younger people might say they'll hit their 40 45 hour work week by splitting themselves at 3 different employers, 4 different employers, and are we, are we going to an era of much more flexibility on the part of workers but also on, on companies, or. Uh, and this idea of somebody being a full-time employee for quite a while, is that, is that, uh, Phil, I think that era is here. I think it's already happening. I mean, when we talk to young folks today, I mean, I'm sure you guys like have this too, they have their blog or their YouTube channel or the book they're writing on the side or the consulting that they're doing. I mean, they already are really living into this portfolio career vision. I think, um, you know, it's kind of our, our social norms and our. Kind of idea of what's happening with the career has yet to catch up with that, but the reality on the ground is people are building these, these multifaceted careers already. Yeah, we, we see it. I see it in my own children, and I, I see it across the board that, and for us we see a lot of the young talent comes in. They start as a community associate. They grow there a little bit, and then they move to other companies and there's no longer. And, and I think that's great because they learn different skills at each location, each different thing that they do. So in our, in our last, uh, minute together, say something optimistic for young people, people in their twenties. Why should they be optimistic about their career and job prospects? Well, um. I, I think the opportunities out there if you embrace the tools that we have, whether it be the AI tools and all the other tools they're going to be tremendous. This next growth period, if you look historically when new technology gets introduced, the growth period is amazing. There's that bumpy ride and then it takes off and you just think, look back over history and so, um, and the other part of it is. That you know the baby boomers are retiring, so there's an opportunity to fill those spots going forward. So, um, I would look at it with bright eyes if I was 25. Great. So on, on that note, uh, thank you both for joining us today and, uh, here's to young people and old people alike and everybody in the middle. Thank you.