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HB Hayden Brown Chief executive of Upwork, on Masters of Scale about verified work-history data as a defense against AI-inflated résumés and about AI agents attempting freelanc...

“The failure rate of agents is incredibly high. They almost never succeed in delivering even fairly simple tasks from clients end to end.”

Masters of Scale · Startups & Venture · August 2026

“The failure rate of agents is incredibly high. They almost never succeed in delivering even fairly simple tasks from clients end to end.” — Hayden Brown, Masters of Scale

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.

Masters of Scale · 2026-08-18 Listen to the episode → More from Hayden Brown → More Startups & Venture quotes →

Transcript

Masters of Scale Around 08:06 into the episode
Hayden Brown

…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.

Bob Safian

…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.

Hayden Brown

…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.

Speaker 4

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.…

Bob Safian

to

Speaker 4

you when it first started?

Speaker names from our own diarization · position estimated from where the line sits in the episode

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