Tech
Zillow at 20: Real estate giant leans on AI to make homebuying hurt less
When Jeremy Wacksman joined Zillow Group in 2009, his first job was getting the upstart real estate site onto the iPhone. Now, amid a generative AI boom, the CEO says the next platform shift is even bigger for Zillow than mobile — and so are the company’s ambitions.
“It’s going to enable all of our services to just be a lot smarter and a lot more intelligent and a lot more personalized,” Wacksman told GeekWire. “And I think it will help us solve the problem we’ve been after forever: how do we digitize the transaction, and how do we actually integrate and remove all the busy work and the redundant paperwork and the errors and the pain of the transaction?”
Zillow built its brand by letting people window‑shop for homes and by generating advertising revenue from real estate agents. More than 200 million people visit Zillow’s apps and sites on a monthly basis. But now, as Zillow marks its 20th anniversary on Monday, its leaders are pushing toward something bigger: a “remote control” that keeps buyers, agents and lenders inside Zillow for the entire home-buying experience.
It’s part of a “housing super app” strategy the company first laid out several years ago, following the failed attempt to build Zillow Offers, its “iBuying” home-flipping business. Zillow remains focused on finding ways to streamline how people buy homes beyond search and alleviate what can be a stressful process.
“More than half of buyers report that they cry during the transaction process,” Wacksman noted.
While Zillow’s traditional advertising business still makes up a majority of its revenue, it has made a bigger push into mortgages — which grew 36% year-over-year in the third quarter of 2025 — as well as rentals, which grew 41%. Zillow, which reports fourth quarter results this week, is also piloting closing services.
The shift marks a deliberate move away from a model where Zillow made money when a shopper raised a hand, toward one where it participates in — and tries to simplify — the entire transaction.
Executives see AI as central to the super app play. Zillow CTO David Beitel, who has led technology efforts at the company since 2005, said the new capabilities of large language models feel “pretty monumental.”
He said AI models have improved so much and so quickly that there is no single part of the business where Zillow isn’t exploring how to harness them.
“It’s really starting to change the way we think about presenting information and change the way that we interact with our customers,” Beitel said.
Long before Zillow launched an app within ChatGPT, the company has used AI in some form since its early days. It applied machine learning to create the “Zestimate” home value tool and later built out computer vision tools to enhance listings.
Now the company is using AI to boost CRM tools for real estate agents — summarizing calls, drafting follow‑up messages, prepping next‑step checklists, and reducing repetitive data entry. Zillow says agents have sent millions of AI‑assisted messages, and that those tools are improving conversion.
Inside Zillow’s own walls, the shift may be even more dramatic.
Beitel said software teams are shipping more code with the same headcount thanks to AI‑assisted development — in some cases, up to a 15% improvement in productivity. The company also uses internal copilots that sit on top of documents, Slack conversations and email, letting employees ask natural‑language questions against Zillow’s own data. Recruiters are using AI to help schedule interviews and coordinate with candidates.
Just in the past two years, Beitel said, the company has “much higher expectations of our team about embracing these tools and using them in their daily jobs.” Zillow encourages experimentation but stops short of mandating specific tools across every team, letting managers decide how to adapt LLMs to their own workflows.
Both executives stressed that, for all the automation, they don’t see AI replacing real estate professionals. Instead, they framed the technology as the next step in a long evolution that started when agents were gatekeepers of listing books and became guides in a world where buyers already know what’s on the market.
“It’s going to pull away all the busy work, all the back office work, all the coordination, all the data collection — all the stuff that a machine can do — to let the human do a great job of actually being your guide,” said Wacksman, who was named CEO in 2024, taking over for co-founder Rich Barton.
All of this is unfolding against a housing market that Wacksman describes as “bouncing along the bottom.” Existing home sales remain well below pre‑pandemic norms; affordability is still strained in many markets; and even optimistic forecasts call for only modest improvement this year. That puts pressure on Zillow’s bet that it can keep growing revenue at a double‑digit clip by capturing a bigger slice of every transaction, even if there aren’t many more transactions to go around.
At the same time, the company is facing louder questions from regulators and rivals about how much control one platform should have over the digital plumbing of the housing market. Zillow is a defendant in a high-profile antitrust lawsuit from the Federal Trade Commission and multiple states over its multifamily rental listings syndication deal with Redfin — a case that alleges the arrangement stifles competition in the rental advertising market. The company is also defending a lawsuit from brokerage Compass challenging Zillow’s private‑listing policies and a separate copyright infringement case from rival CoStar over the use of listing photos.
Wacksman said it hasn’t changed the core roadmap — or Zillow’s room to grow. He said the company still touches a single-digit share of U.S. transactions. “We can grow our business regardless of what happens in [the] macro, and regardless of the clouds from external forces,” he said.