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Upwork CEO Hayden Brown: ‘There will be plenty of work for humans, even as AI agents do more’

Diane Brady
By
Diane Brady
Diane Brady
Executive Editorial Director
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Diane Brady
By
Diane Brady
Diane Brady
Executive Editorial Director
Down Arrow Button Icon
October 6, 2025, 4:53 AM ET
Hayden Brown CEO of Upwork.
Hayden Brown CEO of Upwork. Courtesy of Upwork
  • In today’s CEO Daily: Diane Brady talks to Upwork CEO Hayden Brown about AI.
  • The big story: Trump pressures Netanyahu to accept Gaza peace plan. 
  • The markets: Broadly up.
  • Plus: All the news and watercooler chat from Fortune.

Good morning. Dayforce will today release its annual pulse survey of roughly 7,000 workers in six countries, showing that 71% of workers have not received AI training in the past year—even though 63% of workers say developing such skills is important. The result is that 27% of the workers surveyed say they’re using AI on the job, vs 87% of executives and 57% of managers.

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Another fascinating front in the war for AI talent is the freelance platforms. On one hand, companies like Upwork and Fiverr have suffered as generative AI has disrupted simple contract jobs like copyediting and translation. But I recently spoke with Upwork CEO Hayden Brown about how AI is enabling the platform to win more business from larger enterprise clients. She cites research showing 63% of executives feel they don’t have adequate talent in-house, which may explain why searches for skills like prompt engineering rose more than 50% on Upwork in the last quarter. Some questions to think about:

What is ‘AI’ talent? Brown says there are 250,000 AI experts on her platform, 80,000 of whom are in the U.S. – “Companies are looking for creativity, problem solving, judgment, people who can move up a learning curve quickly as the technology changes,” she says, “so that’s leading to this AI generalist profile that is becoming much more sought after in our ecosystem.” As AI gets applied to different tasks, functional expertise is as coveted as technical expertise. And how do you know if those AI skills are real? Check the ratings.

What is the future of gig workers? The unemployment rate for Gen Z is more than double the national rate, which means freelance work may be a necessity as much as a choice. While the lack of benefits, risk of burnout and isolation are clear risks, Brown says the desire for flexibility is strong. “Younger generations don’t want to be tied to a single employer,” says Brown, arguing that a portfolio approach allows multiple income streams and lets workers “optimize around where the ROI is highest.”

How do the best leaders think about AI? Leaders who hire contractors to replace more expensive full-time workers probably view AI as another cost-saving tool. Those who instead see a flexible talent pool as a strategic advantage in building a dynamic and flexible company will likely fare better. Brown, for one, argues that “there will be plenty of work for humans, even as AI agents do more.”

Contact CEO Daily via Diane Brady at diane.brady@fortune.com

Top news

Trump applies four-lettered pressure to Netanyahu

When Hamas said it was interested in pursuing the peace deal for Gaza pushed by the White House, President Trump saw it as a positive development, and was disappointed when he discovered that Israel’s Benjamin Netanyahu thought little of it. “I don't know why you're always so f—ing negative. This is a win. Take it,” he told the Israeli leader. Trump later told Axios that Netanyahu has no choice but to accept the deal. “He was fine with it. He's got to be fine with it. He has no choice. With me, you got to be fine.” Ordinary Gazans who spoke to the WSJ urged Hamas to take the deal.

Shutdown layoffs will start if Dems won’t deal

National Economic Council director Kevin Hassett said on Sunday that mass layoffs of federal government workers will happen “if the president decides that the negotiations are absolutely going nowhere” with Democrats in Congress.

Trump sends California guards to Oregon

A federal judge this weekend ruled that the president could not deploy 200 Oregon National Guard troops in Portland, so the president ordered hundreds of California National Guard troops to deploy there instead. He also ordered the Texas National Guard to prepare to enter Chicago. Local officials have made it clear they do not want the troops deployed on their streets.

MasterClass CEO warns CEOs against using AI

MasterClass founder and CEO David Rogier told Fortune that the onset of generative AI has given him back the equivalent of an entire workday, and says CEOs who don’t use the technology are holding themselves back. “You’re like, ‘I only want to be 80% as productive as I can be,’” Rogier told Fortune.

CEOs want Elon Musk-style pay packages

More CEOs are seeking Elon Musk-style pay packages, but making them contingent on high goals is incredibly risky. That’s according to Todd Sirras, a managing director with consulting firm Semler Brossy, who told Fortune that “It’s more risky to invest in a human being than it is to invest in a machine because human beings break in different and unpredictable ways.”

Sanae Takaichi elected as leader of Japan’s Liberal Democratic Party

Japan’s Liberal Democratic Party chose Sanae Takaichi to lead the party over the weekend, positioning her as the country’s next prime minister. Her more relaxed take on fiscal policy, particularly when it comes to Japan’s growing debt problem, sent the U.S. dollar up 1.2% against the yen following the news.

Must read: “America has become one big bet on AI”

AI spending accounts for 40% of U.S. GDP growth, 80% of stock gains, and government debt is approaching 100% of GDP. That’s not sustainable, argues Ruchir Sharma, chair of Rockefeller International.

The markets

S&P 500 futures were up 0.26% this morning. The index closed up marginally in its last session at a new high of 6,715.79. STOXX Europe 600 was up 0.35% in early trading. The U.K.’s FTSE 100 was up 0.18% in early trading. Japan’s Nikkei 225 was up 4.75%. China’s CSI 300 was up 0.45%. The South Korea KOSPI was up 2.7%. India’s Nifty 50 was up 0.66% before the end of the session. Bitcoin rose to $123.8K.

Around the watercooler

Larry Summers praises Ford CEO Jim Farley’s concept of the essential economy because it doesn’t ‘fetishize manufacturing’ by Jason Ma

These co-CEOs swear by splitting the job: ‘The demands on a modern CEO are close to unsustainable’ by Amanda Gerut

Jeff Bezos agrees with OpenAI’s Sam Altman: We’re in an AI bubble. But Amazon’s founder says the benefits will be ‘gigantic’ by Nino Paoli

Trump says the U.S. can grow its way out of $37 trillion in debt. Ray Dalio’s debt-cycle research says not so fast by Eva Roytburg

CEO Daily is compiled and edited by Joey Abrams and Jim Edwards.

This is the web version of CEO Daily, a newsletter of must-read global insights from CEOs and industry leaders. Sign up to get it delivered free to your inbox.
About the Author
Diane Brady
By Diane BradyExecutive Editorial Director
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Diane Brady writes about the issues and leaders impacting the global business landscape. In addition to writing Fortune’s CEO Daily newsletter, she co-hosts the Leadership Next podcast, interviews newsmakers on stage at events worldwide and oversees the Fortune CEO Initiative. She previously worked at Forbes, McKinsey, Bloomberg Businessweek, the Wall Street Journal, and Maclean's. Her book Fraternity was named one of Amazon’s best books of 2012, and she also co-wrote Connecting the Dots with former Cisco CEO John Chambers.

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