Zillow’s CEO says his friends were shocked when he quit a cushy job at Microsoft—but Steve Jobs led to his success at the $17 billion real estate firm

Success·ZillowZillow’s CEO ditched Microsoft for a ‘money-losing real estate startup’—and credits his career success to Steve Jobs’ Apple App Store launchBY Emma BurleighBY Emma BurleighReporter, SuccessEmma BurleighReporter, SuccessEmma Burleigh is a reporter at Fortune, covering success, careers, entrepreneurship, and personal finance

Before joining the Success desk, she co-authored Fortune’s CHRO Daily, extensively covering the workplace and the future of jobs

SEE FULL BIOThe late Steve Jobs bably didn't know it, but he gave Zillow's boss a major career break

Housing crisis, his friends told him he’d never make money

But Zillow’s current CEO, Jeremy Wacksman, says the time was the start of a new beginning

Real estate’s a terrible market. ’” The Gen Xer explained that his marketing degree is what got him the job at Microsoft—but also, what inspired him to ultimately leave. “Building a duct and then getting that duct ever-present in the user’s mind, that’s been the common theme I’ve seen, and it’s driven my passion,” Wacksman said. “It’s what led me to Zillow and it’s honestly what keeps me at Zillow. ” Wacksman joined Zillow as the VP of marketing and duct, right around the time the late Steve Jobs introduced the Apple app store—and it turned out to be exactly what the struggling company needed

Zillow declined to additional to Fortune

Thanks to Apple’s invention, users could rent out an apartment easily on their phone, sitting in their back pocket

And because Wacksman had spent a quarter of his time at Microsoft working on mobile jects, he was tapped to lead the effort—and saying yes to taking on work outside of his day-to-day responsibilities ved to be a career-defining moment. “I wasn’t hired to [help the company go mobile], I was hired to work on the duct and marketing efforts

But mobile was new, and I said yes,” Wacksman said. “And in many ways, my career was just 15 years of saying yes to the next thing. ” Wacksman slowly rose the ranks over the next decade and a half, assuming roles including chief marketing officer, president, and chief operating officer, before taking the helm as CEO in August 2024

Reflecting on his time at Zillow and the many other ‘yes’ moments he’s committed to, Wacksman said he’s learned to embrace opportunity

There will be times that jects fall through or unexpected challenges come into the fold, but the experiences make for a better leader. “You’ll throw yourself into something and it’ll work, or you’ll throw yourself into something and it won’t work,” Wacksman said. “You’ll have to pivot, but you’ll have learned something. ”Introducing the 2025 Fortune 500, the definitive ranking of the biggest companies in America

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