But Zillow’s CEO, Jeremy Wacksman, says the time was the start of a new beginning. Less than one year later, he ditched his job as a marketing and product manager at Microsoft Xbox to join the real estate startup, despite nervous looks from his friends. 

“Back in early 2009, for those that remember, [it] was not a fantastic real estate market,” Wacksman told Fortune in a 2025 Leadership Next podcast episode. 

“I remember talking to friends and family [that] I was going to leave a job at Microsoft…And they were like, ‘Why are you going to go work for this money-losing real estate startup? Real estate’s a terrible market.’”

The Gen Xer explained his marketing degree is what got him the job at Microsoft—but also, what inspired him to ultimately leave. 

“Building a product and then getting that product 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 product, 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. 

Success came from saying ‘yes’ to responsibilities outside of his day job—including launching on Apple

One of the most pivotal moments for the $10.5 billion real-estate marketplace came shortly after Wacksman joined the business as the VP of marketing and product: Apple was finally taking websites mobile with apps for the iPhone. 

“Six months after I got here, Steve Jobs launched the App Store on the iPhone, and it became clear that this company that had 100-plus people and was a great desktop website needed to go into mobile,” Wacksman recalled to Fortune’s Kristin Stoller and Diane Brady. “Mobile was going to be the future.”

Now, many online businesses, from Zillow and Airbnb, to eBay and Etsy, all have their own bespoke apps to bring convenience to customers. 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 projects, he was tapped to lead the effort—and saying yes to taking on work outside of his day-to-day responsibilities proved to be a career-defining moment. 

“I wasn’t hired to [help the company go mobile], I was hired to work on the product 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 projects 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.”

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