Startups & Venture · August 2026
Upwork CEO Hayden Brown, discussing what happens when clients try to have AI agents deliver freelance work directly through the platform without a human in the loop. She contrasts this with the much higher success rate once a human expert is added back in.
Transcript
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. At 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. 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, as you were thinking about this, you're like, well, do I lean into that part of the messaging? Because maybe, you know, 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, but 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. They 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 forths with an expert selling 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 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?
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