Zillow’s CEO reveals friends were stunned when he left a comfortable Microsoft job, but Steve Jobs fueled his success at the $10.5B real estate firm

(SeaPRwire) –   The 2008 economic collapse left deep scars on the American psyche, defined by mass unemployment, families struggling to make ends meet, and a failing real estate sector.

However, Zillow CEO Jeremy Wacksman views that era as a turning point. Less than a year after the crisis began, he left his position as a marketing and product manager for Microsoft Xbox to join the real estate startup, despite the skepticism of his peers.

“In early 2009, as many will recall, the real estate market was in a very difficult place,” Wacksman remarked during a 2025 appearance on the Leadership Next podcast.

“I remember telling my friends and family that I was leaving Microsoft… and they questioned why I would join a loss-making real estate startup when the market was so poor.”

The Gen X executive noted that his marketing degree helped him land his role at Microsoft, but it also provided the impetus for his departure.

“My passion has always been creating a product and ensuring it stays at the forefront of the consumer’s mind,” Wacksman stated. “That drive brought me to Zillow and is what continues to motivate me there.”

Wacksman arrived at Zillow as the VP of marketing and product just as the late Steve Jobs unveiled the Apple App Store—a development that proved vital for the then-struggling firm.

Growth was driven by taking on extra-departmental tasks—including the Apple mobile debut

A defining moment for the $10.5 billion real estate platform occurred shortly after Wacksman’s arrival: Apple’s move to bring web experiences to mobile devices through iPhone apps.

“Six months into my tenure, Steve Jobs introduced the App Store, and it was clear that our company, which then had about 100 employees and a strong desktop presence, had to transition to mobile,” Wacksman told ’s Kristin Stoller and Diane Brady. “Mobile represented the future.”

Today, numerous digital businesses, including Zillow, Airbnb, eBay, and Etsy, utilize custom apps to enhance user convenience. Thanks to Apple’s innovation, people can easily manage real estate needs from their smartphones. Because Wacksman had dedicated significant time to mobile projects at Microsoft, he was selected to lead this initiative. Accepting this responsibility outside his core role became a landmark moment in his career.

“I wasn’t specifically recruited to lead the mobile transition; my focus was on product and marketing. But mobile was the new frontier, and I accepted the challenge,” Wacksman explained. “In many respects, my career has been defined by 15 years of saying yes to the next opportunity.”

Wacksman climbed the corporate ladder over the following decade and a half, serving as chief marketing officer, president, and chief operating officer before being named CEO in August 2024.

Looking back at his career and his willingness to take on new challenges, Wacksman noted that he has learned to value every opportunity. He believes that while some projects may fail or face hurdles, the resulting experiences create stronger leaders.

“You might commit to something and see it succeed, or you might commit and see it fail,” Wacksman said. “You may have to change direction, but you will have gained knowledge in the process.”

An earlier version of this article was featured on .com on July 2, 2025.