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Shark Tank's Kevin O'Leary says if he were 25 today, he'd chase these two booming opportunities in the world of AI

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Shark Tank's Kevin O'Leary says if he were 25 today, he'd chase these two booming opportunities in the world of AI

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Even as Elon Musk calls philanthropy ‘very hard,’ everyday Americans gave a record $617 billion—despite feeling the squeeze over the cost of living

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The stock market is about to suffer a 'snapback' and will lose much of this year's gains as 'speculation is hitting extreme levels,' BofA warns
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Zillow CEO doubles down on remote-work model: ‘There is talent everywhere in this country’

Marco Quiroz-Gutierrez
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Marco Quiroz-Gutierrez
Marco Quiroz-Gutierrez
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Marco Quiroz-Gutierrez
By
Marco Quiroz-Gutierrez
Marco Quiroz-Gutierrez
Reporter
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May 17, 2026, 7:57 AM ET
Zillow CEO Jeremy Wacksman.
Zillow CEO Jeremy Wacksman.Steve Vargo for Fortune
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While some business leaders are leaning hard on return-to-office mandates, Zillow’s CEO is taking the opposite approach and seeking talent wherever they are based.

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CEO Jeremy Wacksman, who has led the company since August 2024, said the decision to cultivate a remote-first workforce—an effort the company calls “CloudHQ”—has led to stronger demand for its jobs across the board.

“For us, we see huge benefits in recruiting. We now have employees in all 50 states, whereas before we had them only in a handful,” Wacksman said on the Fortune Leadership Next podcast in 2025. “There is talent everywhere in this country.” 

The real-estate company’s remote-first efforts stand apart in corporate America, where many large companies are forcing workers back to the office. Even in tech, where companies have traditionally been more flexible, industry stalwarts such as Amazon have pushed for five days in office, while Meta and Apple have opted for at least three days.

But Zillow wasn’t always like this. Before the pandemic, Zillow, like many other companies, had a strong in-office culture, Wacksman said. But since then, the company has made a conscious decision to change, and now, even Wacksman works from home when he’s not at an in-person company retreat or town hall.

Although the approach, like any, isn’t perfect, Wacksman said, being transparent about both the benefits and drawbacks is a must. In the end, Zillow found a remote-first approach best fit its mission, size, and unique workforce. 

“We leaned in early. And, again, we really pivoted the company. We didn’t start the company this way. And what that means is you have to rebuild the cultural norms around that,” he said. 

Being remote-first has also helped Zillow improve its systems to drive conversations about performance and collaboration, forcing it to measure and act on new data. On the downside, not being in-person every day has presented a challenge for colleagues wanting to bond and relate with each other, Wacksman said. 

Zillow has tried to tackle this issue with in-person gatherings that give employees the chance to “travel instead of commute,” Wacksman said. During some of these events, employees gather in the office and tackle a problem together or learn new skills as a team, he added.

“It’s things maybe you were doing all the time, and you just kind of bring them together and concentrate them—and you’re just more intentional about when you do things so that you can take advantage of being together in person,” Wacksman said regarding in-person get-togethers.

A version of this story was originally published on Fortune.com on July 2, 2025.

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Marco Quiroz-Gutierrez
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Marco Quiroz-Gutierrez is a reporter for Fortune covering general business news.

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