Earlier this month, Jeremy Wacksman was named CEO of Zillow Group, the real-estate marketplace company that has the online home-search market cornered. The promotion comes as company cofounder Rich Barton heads for the door; Wacksman was the heir apparent, owing, among other things, to his unusually long tenure.
Fifteen years in one place may sound like a long time—and indeed it’s more than triple the typical tenure these days. But to Wacksman, he told Fortune in an interview shortly after his appointment, “it’s felt like a new job every 18 months; that’s how I characterize my time here.”
Indeed, Wacksman, 47, has worn an array of hats over his time at the 18-year-old firm. He left a “very stable job” at Microsoft in 2009 for Zillow, where he first worked as a marketing and product management lead before ascending to chief marketing officer, and later president, and finally COO—his most recent role before taking the corner office.
The company he’s now helming bears little resemblance to the one he joined; during the 2009 financial crisis, Zillow “was a money-losing operation,” he recalled.
But it was the small team and the cofounders, Barton and board chairman Lloyd Frink, who drew Wacksman in. “They said something to me at the time that I remember,” he noted. “If you solve a customer’s problem, everything else will take care of itself.”
Barely getting started
“Shopping. Dreaming. Gawking.” That’s how most people know Zillow, Wacksman said. Look no further than the ubiquitous Twitter/X account Zillow Gone Wild, which documents some of the most garish and bizarre interior design you can find in the app. The account boasts north of 660,000 followers and enough of an audience to warrant an accompanying newsletter. (The real and markedly less raucous Zillow, meanwhile, has about half the number of X followers on X.)
But Wacksman isn’t looking to go viral so much as democratize homebuying. “Our first decade-plus was turning on the lights in real estate,” he said. “It’s hard to remember, but in the beginning, the internet hadn’t come to real estate. People didn’t realize you could go see other listings, get hi-res photos, and virtually tour properties with 2006-era tech.”
That underpinned Wacksman and his teams’ mission. “A more empowered shopper is better,” he recalled thinking. “That leads to more, better transactions—and hopefully a happier customer.” The customer, for most of Zillow’s lifespan, has been anything but happy.
Half of all homebuyers cry at some point along the journey, Wacksman said, citing Zillow’s own data. That’s why he isn’t satisfied when people say they love using Zillow; if the home purchase led to tears, there’s work left to be done. His hunch: “The actual transaction is still not digitized,” he said. “It’s not online. It’s a big, complicated transaction with a lot of fraught coordination.”
Zillow may well have brought the fantasizing and window-shopping experience online, but it hasn’t yet digitized the actual buying and selling, which was a large part of Wacksman’s mission as COO—and his primary charge as CEO. It excites him, he said, because of just how complex it will be to solve.
Head in the clouds
Much like Brian Niccol, another new CEO of a Seattle-based company, Wacksman leads his publicly traded firm entirely remotely. But unlike Starbucks, Zillow’s whole employee base is remote-first, too.
Since the early lockdowns, Zillow has embraced “CloudHQ” as its primary model, which caters to work from home with a small handful of “center of gravity” offices throughout the country; it shed two-thirds of its footprint during the pandemic.
Zillow had a staunchly pro-office culture prior to the pandemic, but “very early on, we declared we’d challenge our own assumptions and shift to being cloud-focused,” Wacksman said. “We’re clear-eyed that that’s who we are. We iterate and try things, we listen to our people, and we try to create an environment for people to do their best work.”
That’s also a cornerstone of their recruiting and retention approach: “Treat adults responsibly, and set them up to do their best work.” The CloudHQ model has underpinned Zillow’s outsize popularity among job seekers; Wacksman said the firm gets about quadruple the number of job applicants per listing now than pre-pandemic. “For sure, there’s a strong demand for flexible work,” he said.
Action items
Wacksman is staring down a daunting strategy challenge: complete digitization of a fully face-to-face transaction with no room for error.
“Think of booking a flight, reserving an Airbnb, or calling an Uber from your phone,” he said. “The end-to-end experience is all there on the app.” Then there’s buying a home, which, naturally, has to conclude in the natural world.
“You and your buyer’s agent have to work with the seller, seller’s agent, loan officer, title officer, escrow officer, and a myriad of other parties,” he explained. “It’s a big challenge.” In the short term, that means Zillow is working on software to bring, bit by bit, more of the interaction online. It’ll be front and center for the first years of his tenure. “It’s so complex because you can’t jump into one universe on your own,” he said. “You’re not buying a good from a company. The whole system needs to be more digitized.”
Naturally, that need lends itself to AI, which he embraces. It “has the potential to really accelerate a lot of our stuff,” Wacksman said. “We at Zillow are no strangers to AI.” Most people don’t know Zillow was founded in 2006 with the “AI of the day,” he said, and has since relied on it to personalize the site, automate workflows, and outsource “low-value work.”
“AI is not a blanket you just throw over an industry and it changes everything magically,” he said. “It’s a tool you have to use.” That’s especially true for a real-estate app, existing in an industry with a six- to nine-month transaction cycle. “We’re excited, but it’s early; I think it’ll take a while for this stuff to play out at a scale.”
Wacksman appeared at the Fortune Brainstorm Tech conference earlier this summer, speaking on a lunch panel about what capabilities an AI copilot might have. “Ideally, it helps a real-estate professional do their best work.”
Even so, every agent and buyer needs something different. “What makes a great agent in Phoenix is very different from in Seattle,” he said. “All real-estate professionals love client service, sales, and helping people. They don’t love the paperwork and factory part of it. AI solves the factory part of it; that’s the potential.”
Wacksman likened it to the difference between interacting with a checkout clerk at a store, versus seeing the nuts and bolts behind the employees-only door. “There’s a whole bunch going on back there” that could be ripe for AI automation—while still leaving the human element maintained face-to-face.
“You only do this once every eight to nine years, on average,” he said. “You’re not an expert in the transaction, and it’s a large financial decision that you want to get right.” That winnows the margin for error way down—no hallucinations accepted.
More is more
A word on the housing market: In the macroenvironment, America is woefully underbuilt. “We just don’t have enough supply,” Wacksman said. “There’s not enough inventory being built, and we don’t have enough home inventory coming online as listings. That is the overall macro challenge.”
Inventory is down 30% from pre-pandemic levels, and prices are sharply up. “The relative relief is helpful, but getting back to a healthy supply-demand balance will take more inventory,” he said. That far-off goal may be cold comfort to the millennial demographic, despondent and depressed over their circumstances, which make it seem quite likely that they’ll never own a home.
What would Wacksman say to them? “Hopefully, things will get better—that’s my short answer,” he said. “They’re right: Look at every year going back to the ’70s and ’80s, and look at today. It’s not a good sign. You never want to be at all-time highs for prices or lows for inventory.”
But Wacksman remains optimistic, and hopes young would-be homebuyers are, too. “What I can say is, hopefully we’re further towards the end of the storm than the start. Forces can work together to rebalance the market.”
Namely, as mortgage rates come down, prices will become more affordable for the masses, and a bunch of sellers will become “unstuck” with their inventory.
“Many people are sitting on a very low mortgage rate, and don’t want to become a buyer,” he explained. “Rates coming down will unstick more inventory, and more supply against the same demand should ease prices. These things should feed off each other over time.”
Nonetheless, Wacksman concedes that “we’re at some real extremes right now.” Home turnover usually averages between 5.5 million to 6 million per year; now, that rate hovers around 4 million, which he admits is “daunting” but hopefully temporary.
He and his Zillow team are staunch advocates for upping supply. “We need to work on how historically underbuilt we are; we haven’t built back up since the financial crisis, and over time the marketplace should correct that problem.”
The outlook isn’t terrible. “We’re past the eye of the hurricane,” he insisted. “It seems we’re closer to easing rates, and closer to supply coming online than we were two to three years ago.” Zillow forecasts a cloudy near-term future for the housing market, “but we’ve suffered through quite an abnormal period, so we should start to see balance come back.”
Wacksman bought his first home, in Austin, in his mid-twenties. He was working at his first job after college, and he called the purchase a relatively inexpensive starter home in the Austin suburbs—where most spots were relatively inexpensive. Now, he acknowledges, the same area is “incredibly unaffordable.” (Though it’s a gold mine for renters.) But back in the mid-2000s, “you could get [a home] for $200,000.”
To Wacksman’s point about greater inventory, Texas still has lots of room to build more houses; the city of Austin is “unrecognizable” from when he lived there two decades ago. Granted, he still was ahead of the curve when it came to buying property.
“The average homebuying age is late-thirties,” Wacksman said. “And that keeps moving up, because people have to delay the purchase. But the demand is still there, and demand on the supply side is still there. The number of people who want to move and sell their home is at an all-time high.”
