How Zillow CEO Jeremy Wacksman is using AI to transform the real estate industry—for buyers, sellers, and agents

Listen to the episode or read the transcript below.

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Jeremy Wacksman: If we ask 100 people on our site, or 100 million Americans, nearly half of them will say they want to move in the next two or three years. Well, obviously that’s not true, right? About 4 or 5 million people actually move. But that long gestation period is what makes this category so fascinating because while you’re thinking about it, you’re dreaming. You’re imagining what your life might be like in a new place, a new neighborhood, a new type of house. Do you want to fix up your old home? Do you want—what is your neighbor’s experience like? And that is a huge and healthy part of getting ready.

Diane Brady: Hi, everyone. Welcome to Leadership Next. The podcast about the people…

Kristin Stoller: …and trends…

Brady: …that are shaping the future of business. I’m Diane Brady.

Stoller: And I’m Kristen Stoller.

Brady: And this week, we are speaking with Jeremy Wacksman of Zillow.

Stoller: Yes. Catching him at a very interesting week.

Brady: Yes. Well, let’s see—we should take bets. Is he going to talk about this lawsuit from Compass, which accuses Zillow Group, of course, being—I shouldn’t say of course. I don’t think it’s the case—of being a monopoly, of gatekeeping. Let’s unpack this a little bit.

Stoller: Yeah, well, I think you and I are certainly going to ask about it. But Zillow, in April, made this rule that if a listing is marketing to any home shoppers, it should be marketed to every home shopper.

Brady: Fair enough, say I.

Stoller: Yes. And Compass is saying, you know, listen, we like to do these private listings to give home sellers a chance to test the market, try out the prices, et cetera, et cetera. So I wonder who will win.

Brady: Well, they’ll have their day in court, but I will tell you, Zillow was one of the favorite apps of my kids growing up, because every time we’d go into a new neighborhood or a new city, up would come the Zillow app, and they’d start looking at home prices and trying to guess which house was worth how much. It was quite a game. And I think one thing about Zillow: It has this oversight of what’s happening with affordability in houses, hot housing markets, ones that are on the wane, you know, really fascinating stuff.

Stoller: It’s very depressing to look at those. In fact, I cry about it a lot because, you know, I’ll never own a home as a millennial.

Brady: Well, in New York City—talk about renting a home. You know, rental prices went up 8.6% in 2023. Wages only went up 1.2%. I think that was a factor in why Zohran Mamdani won the Democratic primary, also news this week, and housing affordability, rental affordability…

Stoller: Big issue.

Brady: Big issue. I think there’s a lot to talk about there, and few people will have more insight into what’s happening…

Stoller: …than Jeremy. And another big issue, which I love to talk about, is the return-to-office debate. And as you know, I have spent the entire month with Zillow.

Brady: Yes, you are. Kristen is all about Zillow.

Stoller: I am. So first…

Brady: COO.

Stoller: Our COO summit in Scottsdale, Arizona, a few weeks ago. Their COO, Jun Choo, was there with us. In May, we had our Workplace Innovation Summit, and their chief people officer Dan Spaulding was there with us, and I got to sit with him at breakfast for a very rousing debate with our table. He was trying to convince all the other CHROs, chief people officers there to go fully remote, like he is. And a lot of people didn’t agree with him. But he said remote work isn’t a perk. It is a business strategy. They are very intentional about…

Brady: Says the man in real estate. Well maybe it’s good for them, right? [Unintelligible] people go off to Indianapolis and other parts of the country. They can work anywhere. So that’s one reason certain markets are hot. We, of course, are five days a week, and love it. So…

Stoller: Well I will say, one thing that Dan said that was interesting is that companies, or his company specifically, they get access to a bigger talent pool. Their job applications quadrupled since they did this, allegedly, so…

Brady: Well…

Stoller: …works for someone.

Brady: All those… How to manage people on a beach by Jeremy Waxman. Well, lots to discuss, and we’ll be right back.

Brady: The best business leaders today know the value and importance of empowering those around them, personally and professionally. By encouraging and enabling others to grow, take risks, and fuel innovation, business leaders are not only driving greater engagement and performance, but also future-proofing their organization for years to come. I’m joined by Jason Girzadas, the CEO of Deloitte US, to talk more about this. Welcome, Jason.

Girzadas: Well, thank you, Diane. Great to be here.

Brady: Innovation is about empowering the people around you, and that’s something that a lot of CEOs struggle with. How do they embed it into their leadership style?

Girzadas: Well, I think there’s all types of CEO leadership styles, clearly, and proven that there’s maybe not one recipe for success, but it does require, I do believe, a commitment to inclusive leadership, where all are expected and invited to contribute around innovation. I think there’s also a collaboration and a collaborative culture that’s a requirement that’s also not something that maybe comes as naturally and has to be cultivated and be intentional about. And then also, I think giving leaders some autonomy to actually look at opportunities for innovation, look at opportunities for creative, new ideas to bring forth that requires a degree of trust and a degree of openness by CEOs in particular, to allow for that within an organization.

Brady: So Jason, I want to—on a personal note, I’m talking to a CEO here. What are some of the most effective strategies you think for fostering open dialogue, collaboration? A lot of what you’re talking about is the ingredients to innovation.

Girzadas: Well, for me, it starts with being genuine and authentic as a leader. Being clear that the single leader doesn’t have all the answers to every question, and certainly in my case, it’s inviting a very broad organization to participate in addressing the issues and challenges that we face. So I think that genuineness and that transparency and authentic leadership style is the key ingredient from my experience.

Brady: Good advice. Thanks for joining us, Jason.

Girzadas: Thank you, Diane.

Brady: So, Jeremy, good to see you. We are catching you on a week where, sir, you have lots in the news. Tell us about this Compass lawsuit.

Wacksman: Good to be here. Thanks for having me. Yeah, maybe we start with what’s topical. There is a big discussion in the industry right now about listing access, and the lawsuit is about rules and how the industry is evolving to ensure that buyers and sellers can see all the listings. I think many folks don’t pay attention to our industry enough to understand: The U.S. is the only market in the world where we, as buyers and sellers and our agents, can see all the listings for free. You can go to a Zillow, you can go to Realtor.com, and you can see them all—and your agent can, whether they work at a brokerage that has five or 5,000, right? And the rules of the industry have some cooperation in place to make that happen. Zillow really supports that cooperation. And there are a handful of companies that really want to undo that cooperation and really put the internet back in the box and keep their listings for themselves, and really make you pay them to see access for those listings. And we don’t think that’s good for buyers and sellers, so we have stood with the industry to have Zillow have the same standards that most MLSes and the structure of the industry have, which is make the listings available to all. And the lawsuit is really about that and challenging that. But if you zoom out and think about that industry, the transparency we have in this country, which is really unique, is so beneficial for buyers and sellers, and that’s really what we are all about at Zillow, right? We are about ensuring a buyer, a renter, a seller, a homeowner, can get information, can get tools, can get services, so that they can feel more empowered to complete a real estate transaction. And we can talk a lot about how we’ve built the company and the brand and the experiences we have, but these industry rules are really just the latest example of that, and you’re going to see Zillow go where the buyer and the seller want us to go. If we see something that can help us all as consumers, we’re going to advocate for it.

Stoller: Jeremy, one of the things I’m hoping you could help explain for me and others who might not be as familiar with the industry as you are, is that you know Compass and their CEO, who’s been very publicly posting on LinkedIn all about this, is saying, you know, they are really a fan of these private listings because they claim it helps sellers to test the market and do things like that that are beneficial to them. Is that true? Or what do you make of that?

Wacksman: Sellers have all kinds of choice right now. And I think that’s the part that maybe gets swept over in headlines or in other perspectives. A seller can test the market with their agent in a private listing rght now. The MLS allows for that. A seller can hide the address if they have a security and a privacy concern, right? A seller can actually share their listing with only the agents in a market and take it off the internet and not have it on Zillow or Realtor.com. All of those choices exist today. So the American buyer and seller has all of the choices they need right now. I think the challenge and the push for this change is about velvet-roping listings for the benefit of a company. And, you know—so that’s the part that we don’t think is good for buyers and sellers, and we want to make sure—sellers and buyers have all kinds of choice right now, and we make sure that the choices they have, that they’re available to them, and most importantly, they understand what those choices are and what those trade offs are.

Stoller: You keep saying MLS. I just want to quickly define that for people—many, like me, who don’t know what that means.

Wacksman: Yeah, the—again, the reason the U.S. real estate market is so transparent is because there is this collaboration between all of the brokerages, and that’s the Multiple Listing Service. That’s MLS. It is effectively a database where everyone shares listings with each other. And that’s what powers not just Zillow—we get our listings that way. We don’t have to, but we get them that way. But any other brokerage website you go to in your city, you can see all the listings, and they are freely available. And so that’s one of the services that that structure provides. But that cooperation amongst brokerages is something that is a rule set for the industry, and that’s the part, hat’s what all this is about is that as being kind of challenged in today.

Brady: You know, it’s interesting. One of—because you do have all the listings, when my kids were growing up, the Zillow app was very popular in our household because they’d call it up the minute we get to a new city, a new neighborhood, and try to guess which houses were worth, so you know, how much. Have you—how much do you feel like Zillow is just part of the zeitgeist now? I mean, how do you think people use it for reasons other than just buying and selling and renting?

Wacksman: We love that usage, and that’s really what this industry is all about. I mean, what people I think don’t understand until they spend time in the industry is we have what I always call the widest funnel of any category. We have—hundreds of millions of people are browsing and dreaming and shopping and window-shopping, and only a small fraction of them transact any given year. And again, back to our DNA, our real obsession is about how can we help a homeowner? How can we help your family browse and just be a little bit more informed casually, even if you may not buy for years? Because that is what helps get you ready when you actually do want to go do it. The average, you know, if we ask 100 people on our site, or 100 million Americans, nearly half of them will say they want to move in the next two or three years. Well, obviously that’s not true, right? About 4 or 5 million people actually move. But that long gestation period is what makes this category so fascinating. Because while you’re thinking about it, you’re dreaming. You’re imagining what your life might be like in a new place, a new neighborhood, a new type of house. Do you want to fix up your old home? Do you want—what is your neighbor’s experience like? And that is a huge and healthy part of getting ready, and we lean into that. And it is, I think, part of why the Zillow brand has become so synonymous with the category. It’s why we have this huge trust with so many Americans, because we are happy to let you do that. And part of what we do every day is trying to figure out, how do we make that better? We’re not in a hurry to turn you into a transaction, because this is helping you get ready.

Stoller: Diane just mentioned Zillow Gone Wild, which I think is the the most fun.

Brady: My friend calls it homemaker porn. But, yes. No need to comment on that.

Stoller: But how do you feel about accounts like that, or things like that? And do you ever plan to make it part of your own business strategy?

Wacksman: I think when you see Zillow Gone Wild, when you see Saturday Night Live repeatedly spoof Zillow, when you see, you know, pop culture references to it—as a marketer, you know, that’s our dream, right? The organic and the earned media that you get for your brand, it’s something that just shows that your brand is really delivering that experience so much so that people want to talk about it. So we love it, and we do lean into it. We, you know, we work—part of our marketing budget is, of course, advertising and teaching you the things Zillow does when you talk about that, right? We are doing new things right now that most of those users and your family doesn’t know we do, but part of marketing is also just leaning into partnerships and content and the zeitgeist to deliver the experience that we do deliver. And so we do love it. I think it’s a great reflection of a brand that doesn’t just deliver value, but has become very synonymous with something that people really love and enjoy.

Brady: Spoken like a true CMO, Jeremy, which is one of the roles you’ve been. COO, CMO, president, I think you were the product leader. Tell us a little bit about how you came to Zillow in the first place.

Wacksman: Yeah, I realized it’s going to be 16 years this fall…

Stoller: Wow, congrats.

Wacksman: …which turns into a long period of time. I met Rich Barton and Lloyd Frink, our cofounders, back in early 2009. 2009, for those that remember, was not a fantastic real estate market. It was the middle of the global financial crisis, and Zillow had actually started a few years earlier and had to go through some tough layoffs early in their tenure because of that. And I remember talking to friends and family, I was going to leave a job at Microsoft. I’d gotten to work on Xbox and some of the consumer mobile efforts, and they were like, “Why are you going to go work for this, you know, money-losing real estate startup? Real estate’s a terrible market.” But for me, it was the team, and it was, you know, the obsession with solving a customer problem. This team had done that in travel, and they’d done that in other places, and it was joining a team to go figure out how to solve problems, build a great brand, and build a great consumer experience. And that’s really what my career has been. I started my career in software engineering. I thought I was going to be a software engineer. I graduated during the end of the dotcom 1.0 boom, and worked for a startup that built and helped bring companies onto the internet. And I got to see fantastic brands thrive on the internet, and then some brands put their head in the sand and not want to buy things to help them learn e-commerce, right? So I got to see great brands early. I got a grad degree in marketing, and that’s what got me to Microsoft, and I got to work on great brands there. But for me, the obsession with solving a customer problem and building a product and then getting that product, you know, ever-present in the user’s mind, that’s been the common theme I’ve seen, and it’s driven my passion. It’s what led me to Zillow, and it’s honestly what keeps me at Zillow. I mean, I think that’s the culture we’ve built here over the last almost two decades is this obsession with—the category is very hard. It’s still very broken. There are parts of it that we delight you with. We talked a lot about, you know, some of that, but a bunch of it, we don’t delight you on. The category doesn’t. Half of all homebuyers and sellers cry during the process of buying and selling a home, and…

Stoller: I’m crying now just thinking about it.

Brady: Kristen’s crying because she can’t afford it. I cry because of the prices you have to pay when you sell it—buy or sell, but tell us a little bit about what you’re seeing right now on the landscape.

Wacksman: Yeah, it is challenging. We have been saying for three or four years now that it’s a very challenging housing market, and unfortunately, I don’t know that it gets any better. The real why behind why it’s challenging is just a pretty strong supply-demand imbalance. Home prices are up nearly 100% from pre-pandemic levels. Obviously incomes are not up that much, so affordability is a huge challenge. Rates are a little higher than they were, although they’re not historically high, but people were very used to 2, 3% mortgages, and 6, 7% mortgages are tougher. But the real issue is, the reason for the home price run-up is lack of supply. We are, we estimate nearly 5 million homes underbuilt. Coming out of the Global Financial Crisis, we started building fewer homes than we needed to keep up with household formation, and that deficit has grown, and we were kind of dealing with struggling affordability until rates went up, and now existing home sellers are just looking at their mortgage and they’re going, “I don’t really want to trade my 3% mortgage for a 7% mortgage, so I’m going to wait, right? I’m not going to list.” And so you have fewer listings, you have fewer new-construction homes, so you have just less supply, and that’s what pushes home prices up. The good news is, that’s also what makes it better when it does get better. And you’re seeing some markets where it does get a little better. You’re seeing Austin, Texas, you’re seeing Florida, you’re seeing the Sun Belt, where they actually did a better job of building over the last few years, both in rental and for sale. Home prices aren’t up as much, and home prices and rent prices are actually starting to go back down. And so, again, supply-demand does balance out over time. We are talking nationwide. I’m sure we can talk about New York, which is its own unique market and incredibly unaffordable. But that is the real way out is if we get more supply online, if we get more sellers to list and get unstuck from their mortgages, you will get back to a more normal market. And to give your listeners a bit of a framework for that, on an average year, about 5.5 to 6 million homes trade. So about close to 6 million people will go through the buying and selling process. Right now, we’re sitting at 4 million. So we are, you know, 50% down from the norm. You are down to the people who have to move, right? There is a level of turnover, of job change, life event, family change, where you have to move, and that’s really where we’re at right now, is the have-to-move level. But imagine what your market might look like if you had 50% more inventory.

Stoller: I think that brings me to my next question, because among my demographic, I think especially for us living in New York City, homeownership is just a bit of a joke for us right now. We just talk about it all the time. But do you ever see a world in which homeownership is attainable again for millennials and Gen Z, and how do you think that happens?

Wacksman: Well, the the affordability imbalance has to ease, but yes, I mean, the demand is still there. I mean, millennials are still buying homes. They’re waiting longer, they’re buying later, and so within that 4 million there are still first-time homebuyers, and part of it is where you buy. So New York may be challenging for even longer, but there’s commutable locations with different home prices, and people make those trade-offs, and they go find where they can afford. And that’s why you see some markets growing so quickly, because there are commuter markets, or there are secondary markets where home prices are a lot more affordable. And then the other side of it is not just the supply-demand piece, but buyers learning what tools are available to them. One of the big myths that a bunch of people come into our category with is they’ve heard this 20% down mantra, or you got to save up and you got to put 20% down to get your mortgage. Most people are shocked to find out, the average first-time homebuyer’s putting down single-digit-percentage down payment.

Brady: Boy, you talk about—subprime mortgage crisis comes to mind. So you don’t think it’ll be repeated. It’s different this time.

Wacksman: No, the regulations are much more stringent now, right? And the creditworthiness of the borrower is much stronger now, and you actually see a lot more—so even though the equity component might be smaller, right, the ability to qualify for the mortgage is still really there. You’re not into these, you know, no income, no asset verification loans we dealt with. But it is about having programs and banks giving programs to let you get in if you are creditworthy, but you just don’t have enough of a down payment. So…

Brady: That’s fair.

Wacksman: There are ways to get it done, and that’s actually a big part of our job is, people don’t know this, and they’re browsing and dreaming and shopping on Zillow thinking they can’t get it done. Well, how can we help teach them, right? They’re not going to…

Brady: You have your BuyAbility tool. I’ve used your BuyAbility tool in the past. I mean, I am curious, how do you innovate in this market when you’re seeing the actual raw supply and activity go down? What are you doing to keep people engaged and excited about Zillow?

Wacksman: The thing we do is we try and continue to make that process better and easier for those that are buying, because then as more buyers come, it’ll be better for everyone. And some examples that you brought up: one, BuyAbility. So that’s a personal financial calculator. It’s tuned to you. So you tell us your financial situation. We give you a sense of your credit score, and then you have a budget that follows you around while you shop on Zillow, and we’ll tell you: Does this home fit in your budget? Will you be able to make an offer on it or not? And that’s financial education while you’re shopping. We also spend a lot of time improving the transaction process. That’s really our goal, back to that “half of all people cry in the process.” They don’t cry because of the window-shopping part. They cry once they push the “I need help” button, and they have to go make three offers before they buy the house, and they have to coordinate with their agent and their mortgage provider and the buyer and seller on the other side. So we’re trying to make all of that easier with software. And the one thing we found over the 20 years is anytime you can bring technology to the process, people will consume it. They will become more educated and empowered. They will spend more time with it, and that does lead to a happier experience, because if you’re more educated as a buyer or seller, you don’t get mis-set expectations. You maybe don’t have as many footfalls through the process. And so that is what we’re doing, is we’re trying to build this integrated transaction, this ability to not just shop, but actually buy and sell, all within the Zillow app. And that’s an experience that, when there are more buyers and sellers, they’ll benefit from it too.

Stoller: Give us some more examples of how you’re using AI to transform your business and the industry.

Wacksman: Yeah. I mean, we have been working on AI since I got here. Obviously, gen AI is new, but the very first product at Zillow was 2006-era AI. The Zestimate. That’s machine learning, right, automated valuation models, and we’ve been doing personalization and computer vision work for a long time. So we can talk about gen AI, but a big part of the experience is computer vision and personalization, because one of the hardest parts of this process is to know which home is right for you, and should I actually commit, right? Because you are committing to this house for a decade. So I’ll give you an example. We are building—we call it a super listing. It is an AI-powered, machine-learning-generated listing where you take the photos and the panoramas that a real estate photographer would do, and we actually generate a full walk-through. You can walk through the house, 360 spin around. You can see an interactive floor plan. So we will tell you on the floor plan where the photos are, so you can get a sense of, well, what’s the light look like, and how much space really is there in this room?

Brady: That’s not a real window.

Wacksman: We now have drone flyovers that 360 spin around the house from a drone photographer. So this is us trying to create really a way for you to virtually tour the home, right? If you’re a real buyer and a real seller, wanting to get a sense of the market, you want to spend as much time as you can virtually, not just physically. And so that’s just one example of us using technology to create a more immersive, more digital real estate experience. We can talk about gen AI too. I’m sure we’ll spend some time there.

Brady: Well, I mean, I suppose we should get—I want to ask about your personal background, but before that, let’s, you know, natural narrative flow takes me to gen AI because I’ve been seeing some amazing stuff with agentic AI recently. Just came from seeing Intuit. They’re doing incredible stuff for small business owners. What’s the—tell me about some of the delightful things you can do on that front?

Wacksman: Yeah, the fascinating thing about this category is it takes so much time and effort and process and busywork, and, frankly, waste work. Not just you and I as buyers and sellers, but we go hire a bunch of professionals that have to do the same thing, right? You’re hiring a real estate agent that’s managing their business and flowing data and meeting with clients. You’re hiring a loan officer to get you your mortgage, and they’re doing the same thing. They’re coordinating with their professionals on the other side is coordinating with the seller. That is all incredibly ripe for not just an intelligent layer of technology to become proactive and fill in the gaps, but an agentic layer to actually maybe do the work for them, to make it more delightful. And that’s where we see I think a ton of opportunity in the short term. We are already piloting AI tools for the real estate agent and for the loan officers, so that it can listen to calls and summarize calls, and it can suggest next steps, and eventually will be able to proactively schedule those next steps. And I mean, if you think about going through this process, if you have been through the rental process or the for sale process, it’s a process where you have to do a lot on your own. You’re hiring a professional, really, as a part-time project manager, among other things, a therapist, right, a negotiator, an expert, but they’re helping you—what are all the things you have to do? And well, now you got to do this well, now you got to sign this document. Well, the bank now needs to know this. Well, I need to follow up with you. Well, did you do this? Those—I mean, imagine if you had an agent that helped you, and if the professional had that agent to help you as the client, get you from start to finish. So it’s…

Brady: And still charges 6%.

Wacksman: …tremendously exciting about what it can do. We’re obviously still very early in actually getting that done.

Stoller: Yeah, and I think it’s interesting, Jeremy, that you kind of serve two different groups. You got the consumers, you got the agents. You’re building tools for both of them. How do you manage kind of serving two different groups whose interests probably don’t always align?

Wacksman: Well, the interests do align at the end….

Stoller: Yeah, there you go.

Wacksman: …because everyone wants to get the transaction done. And that’s a little bit the answer on how we do it. What we—it took us a while, but what we worked out as a brand is, if you want to make the buying and selling process easier, you have to build great software for one side of the screen, right? That’s the side of the screen that you all think about more: the Zillow app. Can I converse with my agent? Can I just fire off a message in the app? Can I get a pizza tracker of where my transaction is? Can I get preapproved? That sounds great, but it only works if you actually also build software for the professionals that are helping power that on the other side of the screen, and that is part of what led us into real estate software and software for agents and technology and systems for the industry as well. We provide a lot of software, not just for individual agents, but for the industry. And it’s because if we want to build this delightful consumer experience, we can’t—we have to build a better way to do it from the buyer’s perspective, but also from the agent’s perspective and the other side of the transactions perspective. That’s what makes digitizing this industry so hard, right? You can’t just e-commerce it and fix one side of it. You have to actually plug everyone in to a digital experience so that we can all have the experience we all want. We get a digital experience from every other category on our phone, and we don’t yet have that in real estate, and that’s what we’re trying to build towards.

Brady: Well, Jeremy, I have to say, when I go to other parts of the world, I’m always struck by how high the broker’s fees, the agent fees are in this country. Do you—the type of thing that you’re talking about would seem to naturally lead to a lowering of those fees, when we can digitize a lot of those tasks. What do you see coming?

Wacksman: We see it more as elevating the profession and raising the expectations of who you hire. I mean, commission rates have come down since the dawn of the internet. Dollars haven’t come down because home prices have gone up more. But the bigger trend, and the pro-consumer trend, has been the elevation of the professional. And I’ll give you an example. Just think about what you hired a real estate agent for before the internet. They had information you didn’t have, right? They had a book of listings, and you had to pay for access to those listings, and you didn’t know if you were hiring someone who was good or met your needs or knew the market. You were just paying for access. Well, now the internet has democratized information and real estate agents, those that still do a great job and have built businesses, they’re local experts, they’re negotiators, they’re counselors, right? They’re salespeople. They help you on what you need, and it has moved the profession from information arbiter to negotiator. And gen AI, I think, will do that further, right? The more that you can do as a buyer and seller on your own, the more educated you’re going to be, and the more discerning you’re going to be at hiring the best professional. And so we see it as, we hope, continuing this trend of elevating and professionalizing the people you hire, because the one thing I think people miss on this category is because you only buy once every 10 years, and because it is so much of your net worth is tied up in this decision, it is not a decision that you’re going to bypass help, right? As you said, Diane, you may wait longer or wait later or be a stronger negotiator when you hire help, but you are going to hire help. Most, the vast majority of us are going to want help in the process. This just maybe helps us know what we want more and have more options in how we hire the professional, and it should help the professional not just do a better job, but actually be more efficient at what they do.

Stoller: Jeremy, if you could rebuild the U.S. housing market from scratch, you know, as crazy as you want, no zoning laws, no legacy systems, whatever you want, what would be the absolute first thing that you would change?

Wacksman: I would try and make it a lot easier to build. Which is something we’re spending a lot of time advocating for is the challenge we have in the housing market, the, you know, the why behind, “Hey, you’re, you’re 5.5 million or 5 million homes underbuilt.” Why? Well, the places where the people are, the urban centers, are the places where they’ve made it really hard to build, right? The time and cost to get a permit, the zoning restrictions and lack of zoning reform to build dense housing and to build affordable housing in the places where we all live, that is the snarl, right? And if I could do anything, it would be to just push to make it easier to build a lot more rental and affordable homes because, back to the conversation earlier,that is the real input to solving the supply-demand imbalance is just getting a lot more inventory online.

Brady: Well, I think that was a factor in the New York Democratic primary victory of Zohran Mamdani, because affordable housing was a big issue there. Let me ask you about your own background, because you actually started out in computer engineering. That was your undergraduate degree. And, of course, you know, went on, I’m sure, to do the MBA. But tell me a little bit about what have been some of the hardest learning—things you’ve had to learn. Because you’ve had a marketing role, a product role, an operational role, there’s a natural flow, I’m sure, to a lot of that. But you know, as a leader, what have been some of the toughest skills to adopt?

Wacksman: As an engineer, the hardest leadership lesson I had to learn was: Saying “I don’t know” is a strength, not a weakness. As an engineer, you’re taught to go solve problems, right? I was never going to be a practicing engineer, but the engineering discipline taught me problem solving. It taught me intellectual curiosity, and I think I’ve brought a lot of those tools to product and to marketing, and it’s just kind of who I am, but it also teaches you that you need to figure out the answer, right? And leadership is actually about empowering others to figure out the answer and to coach and to guide and to learn, which means you’re not the smartest person in the room. You may know enough to be dangerous to help guide a conversation, but you need to be comfortable empowering others and saying, “I don’t know.” And I think that’s something that I see a lot of early career leaders struggle with, too, is you got to your job and you got your promotion because you were the best at what you did. So now you should manage people who do what you do. But that immediately starts to flip the script to where you’re not doing it anymore, and you have to let go, and you have to be okay not knowing as much. So for me, early in my career, learning that “I don’t know” is a strength. It’s not a weakness to say “I don’t know.” It actually disarms the room, and it invites conversation and disagreement and invites analysis and challenging of perspectives. But as someone who was trained to solve problems and to find the answer, that was a very not native behavior for me to learn.

Stoller: Can you point to a specific moment in your career or time at Zillow that you think is the reason why you were selected to become CEO?

Wacksman: I don’t think it was any one thing. I mean, I think it was 15 years of saying yes to opportunities. I came here to work on marketing, and we were just starting to grow, and it was about building the marketing team. We had a great comms and data PR effort, but we really had done no marketing. And I got here, and six months after I got here, you know, 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, and mobile was going to be the future, and we didn’t know anything about mobile. And I had spent maybe like a quarter on mobile at Microsoft. They’re like, “You know a lot about mobile. Go help us figure it out.” And you know, I wasn’t hired to do that. I was hired to work on the product and work on marketing efforts, but mobile was new, but I said yes, and in many ways, my career was just 15 years of saying yes to the next thing. And I say that because that is actually what started to give me the skills. The other thing as an engineer, or maybe as an MBA, is you’re told you have to be really planful and thoughtful about your career, and how’s the ladder going to build. And we use a phrase at Zillow that it’s a career jungle gym, not a career ladder. And I am a shining example of that. I mean, I’ve gone all over the place, and you just learn new skills, and you learn new capabilities, and you have learned experiences from those things, regardless of whether they made sense on some plan. And so we talk a lot about that too. Be willing to just embrace the opportunity and take an opportunity. When you work at a high-growth, fast-growth company, it’s always going to change, and you’re always going to have new challenges and unexpected challenges, and you’ll throw yourself into something and it’ll work, or you’ll throw yourself into something and it won’t work and you’ll have to pivot, but you’ll have learned something, and now your toolkit is bigger and broader. So I don’t think there’s any one thing. I do think having the breadth and getting the experience across the business over time clearly prepared me for the last couple roles I’ve had, and then the last couple roles, I think, have obviously prepared me for this.

Brady: I’m fascinated by the fact you’re an advisor. I know it’s Rover.com, Dollar Shave Club, GoFundMe, I think Room 77. I’m curious the advice you give to them. But let me start with how that helps you do your day job.

Wacksman: When you see other companies and the challenges that other companies have struggled with, you pattern-match. Again, back to putting my engineering brain on. I’m trying to match patterns. And so I was really fortunate earlier in my career at Zillow to get to work with some of these other consumer marketplaces and two-sided marketplaces. That’s what we were building. And so as we were building Zillow, you know, we were going through a huge pivot at Zillow about the same time I was working with some of those companies, where we were moving from an information marketplace, right? We started this conversation about the dreamy and shopping we do on Zillow. Well, V1 of Zillow was just advertising. It was: Connect you with someone when you’re ready to buy and shop, and then we’re out of it. And we are—we have been pivoting the company to a transaction marketplace where we actually provide the buy and sell services for you, and more of them,and how do we integrate them and stitch them together, and what does that mean? And it means changing everything you do. So I got to see and work with other companies that were struggling with marketplace issues, and so I got to learn from them, and then I got to help them on problems we’d solve and things—oh, you were struggling with demand generation in this marketing effort, you know, we’ve done that before. So it was a really great two-way learning experience, where, you know, I could provide value to those brands and those teams, but I could also learn and see, how did things work, not in the real estate industry. And so I was really fortunate to get that experience in my career.

Stoller: Jeremy, I’m going to pivot a little bit because I was telling Diane, I feel like I’ve spent the entire last month with your C-suite.

Brady: All Zillow, all the time.

Stoller: Yes, with Dan, with June, who are great at our conferences. But one of the things that I’ve been talking with both of them about is CloudHQ, your non-return-to-office mandate. And it’s been interesting for me because I can’t find companies to talk to me on the record who have gone back five days a week, and so I would love to hear your thinking and your strategy behind being remote forever.

Wacksman: One of the most fascinating things to me about CloudHQ for us is we were a strong in-office culture until the pandemic. You know, we were 12, 13 years old, and we were built around Seattle and San Francisco and New York. And if you weren’t in the office and you were traveling, it was really painful to be a remote employer, to be on the road. And yet, when the pandemic came and we were forced to go to remote, we saw the benefits of it. And you know, for who we are, for the size company we are, for the type of workforce we are. We saw it really work for us. It really works great for product engineering and design. It really works great for sales. It works great for many roles and for the size company we are in terms of how we manage a workforce and how we grow, we saw a tremendous amount of benefits. And so we leaned in early and we, again, we really pivoted the company. We didn’t start the company this way, and what that means is you have to rebuild the cultural norms around that. You have to change what you were doing. And part of that is being clear about what our strategy is and being clear about what the benefits of it are and then also the drawbacks. There’s no perfect system for how we all work, but we’re just really clear: This is what we’re doing, and here are the benefits of it, and here are the drawbacks, and, therefore, how can we build programs to address the challenges that it gives, right? And so for us, we see huge benefits in recruiting. We now have employees in all 50 states, whereas before, we had them only in a handful, and there is talent everywhere in this country. And we see stronger demand for our jobs than we did before, which I’m sure Dan talked to you all about. We also see better systems internally for assessing and using data to drive conversations about performance and conversations about collaboration. We were a company that did a lot by osmosis in our centers, and this forced us to write things down and to get more systematized in what we manage and how we measure things. So those are the huge benefits. Obviously, there’s challenges with it. One of the big challenges is you’re not in person every day. And you know, relationships are built with nonverbal communication, and humans want to be together. And so we’ve had to build systems to try and not correct for that, but create that outlet. And so we built gathering systems, and we now—you basically travel instead of commute. And some folks, unfortunately travel more than they want, but they also get a lot of time with their teams and with their peers, and it’s really a heightened sense of interpersonal time to then take back when you work every day from home. So…

Brady: I’ve not heard that term.

Wacksman: …for me, it’s more about just knowing what you want to do and being clear on this is our goal. Here’s what’s working and here’s what’s not working.

Brady: So you call it “gathering systems”? I remember Satya Nadella once said he was the chief event officer, and he’s like, “Just because you show up doesn’t mean I have to feed you people pizza.” He didn’t say it like that. I’m paraphrasing, of course. So, how—is it event-driven, then? How do you actually get to know people on a personal level? Can you just give us some of the hacks for others who want to do this thing?

Wacksman: For sure. Yeah, yeah, at one point we called it a Cruise Calendar.

Brady: Cruise Calendar.

Stoller: Dan did say that, which I loved.

Brady: All right, I’m applying to Zillow. That’s it.

Wacksman: We like to put a “Z” in front of everything, so they’re retreats. So we call them zRetreats, but that is—I mean, they’re not events, although the bigger ones are actually planned by our events team, but they are coordinated meetings. So I’ll give you two examples, right? One, we do our Hack Week every year. We’ll do our Hack Week in person, and we’ll bring as many people to Seattle as we can, and we have a big event space in our Seattle office, and folks will spend the week doing their Hack Week projects together as much as they can for part of the week. That’s a good example. That’ll be more of an event that’s programmed because it’s thousands of people. But, you know, just last week, there were 100 people from a team in our for-sale business in the office, working on a problem and spending time together and learning new job skills together, and that was planned by their HR team and their leader. So, you know, small, medium, and big, you know, there will have—functions will bring their entire team together. The entire design team is getting together this week, and that’s a big training effort, you know. The design leaders are taking them through gen AI tools and plans and strategy, and then they’re going to spend time working in groups together. So it’s things maybe you were doing all the time, and you just kind of bring them together and concentrate them, and you’re just more intentional about when you do things so that you can take advantage of being together in person.

Stoller: Speaking of fun, I have a fun question for you, Jeremy. What is the weirdest or most outrageous feature that you’ve seen on a listing on Zillow that you love?

Brady: Let me pull up Zillow Gone Wild here, and I’ll let you know.

Stoller: Ask your kids.

Wacksman: I mean, agents are incredibly creative marketers, and so you see all kinds of good and all kinds of bad. There was a listing that went viral because they tried to make the photos like a horror film. They put, you know, something that you had to really pay attention to, to discover. And I can’t remember what the horror character was, but then it was in a few different photos, and clearly was intentional, clearly was a little subtle and was hoping to get picked up so that it went viral, and it did get viral, and it got tens of thousands of views. And I don’t know if it helped sell the house…

Brady: Did it sell? Yeah.

Wacksman: …incredibly creative marketing of the listing by the agent, for sure.

Brady: Is there anything that that you wish you were asked more often, or don’t get asked enough?

Wacksman: I think the big misunderstood part of our category and of Zillow is actually how big our rentals business is. We’ve just spent a lot of time talking about for-sale and affordability. There are more renters than buyers in this country, and our rentals business is a quarter-and-growing part of our business. And it’s not just that it’s a big revenue business. It’s so strategically important, if you are a company that is trying to help all movers, well, there are more renters than there are buyers and sellers every year, and today’s renters become tomorrow’s buyers when they pick a location and match their affordability that they can, and building up their renter résumé, and building up their credit, and helping them do that while they’re a renter, you know, that is how we help teach people how to become a buyer. But I think that’s the—people know Zillow so much for the for-sale business, and that’s a great thing, and that’s a great—we love that brand, and we lean into that. But people don’t know we are the largest rental marketplace in the country. We have—more renters come to Zillow Rentals than any other site. We actually—if you ask renters, “Name a rental site,” we come up first. And we have the most rental listings. The challenge with the rental market is we spent a bunch of time in the beginning of this talking about the machinations of the for-sale space, but the idea is that all the listings are available. There aren’t all listings available everywhere in the rental space. So what we’ve been doing for the last 10 years is trying to bring as much of the listings online as possible. There’s 4 or 5 million rental listings at any one time. We have more than half, but no one has them all. So, Kristen, I know you talked about being a renter, like when you go to re-rent, you’re scouring the internet for what places are available. We’re trying to get as much of it as possible. So the rental marketplace problem is in some ways harder than the for sale problem, and the volumes are higher and the challenges for a renter. But I think that’s the thing people miss about Zillow is, yes, we have this big residential for-sale business. We’re building a mortgage business, we have a software business, we work with agents, but we also have this growing rentals business, and we actually have more renters on Zillow, you know, renting than we have buyers buying, just because the category is so much bigger.

Stoller: Are you a renter or a buyer?

Wacksman: I’m a homeowner now.

Brady: He’s a homeowner. He’s the CEO of Zillow.

Wacksman: I have been a renter. I’ve done both.

Brady: You know, Barbara Corcoran, I saw a video recently with her, and I know she’s now more Shark Tank than real estate, perhaps, but she did say now is a good, excellent time to buy. What do you think?

Wacksman: I think that answer to that question always depends on your personal situation. And part of being a marketplace is recognizing that, right? Whether it’s good to buy or sell depends on which market are you looking in. There are markets where it’s better to rent than buy and better to buy than rent, and that calculator is based on your time frame, right? So a good agent will always ask you, well, how long are you going to be there? And if you say three years, or if you say 10 years, the calculator is different, right? So it does really depend on your personal situation. And I think that’s what a great professional does, is they meet clients and understand what those clients needs are, and they help guide them to the right decision. And sometimes the right decision is not, you know, going through something and warning someone off of a house that they fell in love with. And that’s what great professionals do. So it is a really personal decision. If you zoom out and give the economic answer, there are many markets where it’s better to rent than it is to buy, but in the markets where it’s better to buy, those markets are softening, and those markets are becoming buyers markets. And if you’ve been waiting for five or six years to buy a house and you find one you like, and it’s a little easier now than it was a year ago, well versus a year ago, it is a good time to buy. So it just depends on your situation.

Brady: Jeremy Wacksman, beloved by real estate agents everywhere. Thank you.

Stoller: Thank you, Jeremy.

Wacksman: Yeah, thanks for having me.

Brady: Really enjoyed chatting with you.

Brady: Leadership Next is produced and edited by Ceylan Ersoy.

Stoller: Our executive producer is Adam Banicki. Our theme is by Jason Snell.

Brady: Our studio producer is Natasha Ortiz.

Stoller: Leadership Next is a production of Fortune Media.

Brady: I’m Diane Brady.

Stoller: And I’m Kristen Stoller.

Brady: See you next time.

Leadership Next episodes are produced by Fortune‘s editorial team. The views and opinions expressed by podcasters and guests are solely their own and do not reflect the opinions of Deloitte or its personnel. Nor does Deloitte advocate or endorse any individuals or entities featured on the episodes.