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Can-One | Fortune

Can-One Company Profile, Stock Price, News, Rankings | Fortune

Zillow CEO Jeremy Wacksman joins Leadership Next to unpack the forces reshaping American real estate—and the friction threatening its transparency. In a wide-ranging conversation, Wacksman addresses the industry lawsuit brought by Compass and defends Zillow’s stance on keeping property listings open and accessible to all. He explains how the current system—a uniquely American one that allows any buyer or agent to view every listing — is now at risk.
With home prices nearly doubling since the pandemic and affordability out of reach for many millennials and Gen Z buyers, Wacksman outlines how Zillow is leaning into AI, computer vision, and immersive virtual experiences to create “super listings” that streamline the buying process. He also shares Zillow’s strategy for supporting buyers long before they’re ready to transact, highlighting the role of casual browsing in shaping the future of homeownership.
Wacksman discusses the emotional weight of buying a home, why nearly half of buyers report crying during the process, and how Zillow is building tools to ease the burden. He also opens up about the company’s remote-first culture, the power of retreats to foster creativity, and why he champions a “career jungle gym” over a traditional ladder.

Home Truths: Inside the Future of Real Estate With the CEO of Zillow

Courtesy of Jeremy Wacskman; Graphics by Fortune

Leadership

Jeremy Wacksman on AI, Industry Shakeups, and Making Home Buying Less Miserable

As the operational backbone of an organization, the strategic ascension of COO to CEO can be one of the most powerful succession strategies in corporate leadership. A COOs comprehensive strategic perspective, cross-functional relationships, and battle-tested decision-making capabilities create the unique foundation for a seamless executive transition and powerful leadership. This session explores the critical elements of CEO succession planning that transform operational leaders into visionary CEOs.  

THE ROAD TO THE CORNER OFFICE: HOW TO SUCCEED IN SUCCESSION

Conferences

Hello, good afternoon. Um, so the COO role is still the most common last stop on the way to the C-suite. I think a recent, recent data showed that 57% of new S&P 1500 CEOs were promoted from the COO world. So I just wanna check in with the audience here. How many people here are interested in making that transition? Yeah, show of hands. OK, great. That's um. And I want to talk a little bit later about like what questions people should ask themselves to find out if they are if that's something that they see for themselves, but I want to start by just asking maybe um Steven, I know that you're advising C-suite executives all the time that you've written a book about COOs riding shotguns. If you were to draw a Venn diagram of the COO job and the CEO job, what traits would sort of land in the middle, overlap and what's outside? Uh, a couple of things to get us going. Hi everybody, it's, it's great to be here. I, I think, um, a mistake many people make is when you've become CEO and you're the #2 inside the company, you think that you know how to do the CEO job and it's absolutely not true. There's no flight simulator for the CEO job. It is a different job. You can do every job inside the company and you haven't been the CEO. And I think what's really, really important is the COO is not a permanent position in most companies, so it's, it creates an artificial org chart and it creates often artificial direct reports in order to achieve an outcome whether it's project based or succession based where the CEO role obviously is permanent. The the big difference for me from going from COO or CFO or one of the sort of C-suite positions to the CEO is the CEO job is a staff job. And I know a lot of people like are sinking in their chairs when I say that, but ultimately to be CEO you have to be good at staff work. And you know, when you look at sort of private and public companies, I think on the private side there's definitely more COO plus if you will, in the CEO job, but if you're the CEO of a public company, you have to do staff work and you have to do it really well. You have to do it at the top end, whether it's corporate finance, shareholders dealing with activists, um, maintaining your license to operate now as a company through governments, regulators, the changing macro. COO job is generally down and in as it's defined most commonly. And so if you think about the, the big differentiation between the two roles, it's win in the business of today. COO, build the business of tomorrow, CEO. And you have to walk the tightrope together in order to deliver the full enterprise outcome when in the business of today and build the business of tomorrow, and that takes different skill sets often. He talked about Howard up here just a few minutes ago from Ancestry, and he was talking about the shift in terms of now he's all about building the business of tomorrow growth in the context that he described. Just a couple of other things that are really different in the CEO job. Number one is you're in the last office. In every other job inside the company, you're not in the last office. You have the last office to go into and what you get really good at is winning. You go in, they need to buy something, sell something, hire somebody, do something. You're really, really good at winning. When you're the CEO and you reside in the last office, nobody's good enough. So what you need to be in the business of now is hypothesis testing, triangulating information. And getting to next best. All I know is if you're the CEO, there is the next best answer. It's across what what time frame. And a lot of people who are really great at operations. You know, tactical short term drive outcomes, deliver the business of today, have developed this winning version of making decisions operationally down inside the company, and they have higher pattern recognition. The CEO job, everybody else does the easy stuff. So when you sit in the last office, you have to triangulate information, you have to deal with non-linear events. You're often formulating a point of view on behalf of the company. There's sometimes not a right or wrong answer, and you got to sort of weave and figure out in the gray area, how to deliver an outcome and have conviction around the outcome. And a lot of people who are used to the touch and feel of outcomes in the in the operational side of the company are really uncomfortable in the gray nonlinear side of the company. That's a great overview. Thank you so much. And and at Russell Reynolds, you're advising CEOs and COOs and boards, and so I wonder if you have anything to add to that, but also, is there anything about like right now this political moment and this moment in technology and you helped build the AI. Um, business in your company, so I'd love to hear what, what you would add. Yeah, happy to and thank you all for having us here. Um, if we just take a moment and, and look around about, uh, on all the conversation we've had since this morning, um, what, what was just mentioned around the uncertainty we're living through, um, between geopolitical and tech technological change that we're going through. Um, the expectation from the CEO is to have all the answers at the end of the day, like have the, the answer that we're gonna go forward with, and whether they got the answers to the use their team or have the answer by themselves, but the expectation is that they will have an answer. And so the and that's changing as you see the technology shifting and exponentially changing and becoming accessible, their expectation from the CEO tends to be seems to be changing and so how we assess CEOs. Um, it used to be a lot more around, um, system thinking, which is that over the last 10 years, system thinking around agility, around drive, um, as well as, um, social awareness. Um, what we're seeing now is 3 things. One is self-knowledge. What can and can I not do? I've been very clear in terms of where do I need help, because today your demands, you're expected to all of a sudden AI is not a tech topic, it's a CEO topic. Everything is becoming a CEO topic. So how do you shift your priorities and adjust for that? Secondly, your values, uh, your value system and aspirations need to be more clear than ever. Everything you're doing is very nuanced. Um, do you, do you take it and use more AI? What does that mean for your workforce, you know, what does that mean for your shareholders? Um, how much are you gonna invest in reskilling? Um, are you gonna cut costs all of these elements require you to have a moral compass that's gonna be very clear for you in terms of how you're going to, um, navigate through this. And the last thing is around legacy. Legacy was mentioned earlier by Scott. Um, today you can you can you're holding the wheel, you've got all of this pressure coming to you, all these advances that you can take, take, uh, forward and, and leverage. You're either gonna hold it tight and keep going straight or you're gonna make a turn, but you're expected to make a shift and, and that's a lot of pressure if you, if you don't have this inner, uh, want to have a legacy. You're gonna be stuck frozen in that moment. So we're seeing a constant shift. We've seen that over the years, but right now it feels like more than ever. So helpful. I'd love to hear a couple of stories of COOs that, um, you know, they found like just the perfect project or the perfect thing to do to sort of demonstrate that they were ready for that next role. And any derailment stories that you can think of like what is a common issue that sort of sends a COO off the path no longer in line for that for the corner office, um, would you like to start? Sure, uh, first derailment story, um, you know, when you're a COO, um, you're not the CEO and you need to be crystal clear on that. And if you start to move into and get out of sync with your CEO, it generally doesn't end well for you. And so in the context of um almost full derailment uh a COO um um really referenced himself as the heir apparent inside the company and then mistakenly referenced themselves as the heir apparent in the boardroom, um, which led to um emergency board meeting and a decision whether to get rid of them. And the board they need to be talked off the ledge because no as boards you want, you, you're the #2, you're the first among equals, but you're not the CEO and they want the ultimate decision to choose their next CEO and not have you thinking and it sort of gets the arrogance and hubris in the process, so. Being very careful there and number 2 quickly is if you don't get the blueprint right with your CEO, it's very important like the COO role is bespoke and it's customized. Everybody in this room would have a customized version of it within the context of their company if it's not a permanent COO. And what's really important is where there is a blueprint is how to synchronize and reduce friction. Uh with your CEO and the number one way you derail and the organization will test the organizational design structure to in the box every single minute of every day, and what they try to do is get the back door open and what they do is they go to you as COO and say make a decision, and then they try to take that decision to the CEO, assuming they want a different decision or slightly different, and see if the CEO will bite. And as soon as they bite, they they erode the entire construct of the CEO COO relationship, and generally that goes really poorly for the COO. So the blueprint and synchronization with your CEO and the consistency of that over time is really important. When it gets out of sync, generally the COO loses. OK, great. And so, um, I, I give a slightly different story in the sense that, um, where, where the succession doesn't go well because the CEO has a change of heart. Um, and this is where you need clear alignment, uh, you know, at the board level, um, and you can't have mixed messaging. Um, we've seen situations where one of the board members becomes a sympathizer and all of a sudden the timeline, although it's been declared internally well known in terms of when it's gonna happen. Um, you know, all of a sudden starts to shift and then you're sending mixed messages to your succession candidates and then your, you know, CEOO resigns who was going to be the CEO and, you know, the rest of the board is annoyed and it's a disaster, right? And so having clarity, um, in terms of the, the timeline and, um, how it's expected to play out is crucial for all parties involved. This is great, such great food for thought here and tips. Um, I'd like to ask the audience if they have anything that they would like to ask these two experts about the CEO to CEO transition. Do you have any questions? Um, while people are thinking, I'll ask you if anybody is sort of on the fence about whether or not they do want to make that move, what are the questions they should be asking themselves? Well I'll go back to what Courtney said, uh, that I think is really important is she talked in the on the construct of Blackstone their investment thesis which shapes the role, right? There's content that drops out of their investment thesis, and she said long term value in a short period of time, but it matters for every single time you think about. CEO role. What's the shape of the company in the future, right shape in the future, and how do you align to that shape in the future and hopefully if you distill your own investment thesis for the company in a 12 to 24 to 36 month period of time, the Venn diagram of your experiences and capability overlays with the investment thesis and the shape. Of the company in the future, it matters where you're in the public or private markets, and it matters for you to be successful. Probability of you being successful if your Venn diagram and motivation and passion for the organization looking forward and the skills and experiences that are required, um, chances of you hitting the ground running go way, way up. Thank you. um, and Fawad, um, any last thoughts when we're talking about public and private companies? Um, is, is there something that's very different when you're looking at that, that move, um. Um, the, the fundamental expectation of the CEO are quite similar in terms of what we look for, um, in terms of what makes them successful. It is a timeline. It, it's this very singular focus on value and how value is created. Um, and this concept of, um, treating your board members as stakeholders versus partners in terms of how they help you navigate it's just a very different mindset and certain individuals are going to be more geared towards that private partnership versus others that are gonna be more focused on, you know, working in a public environment. OK, so helpful. Thank you so much. Um, I, I do want to, you know, we did talk a lot about boards and developing relationships with the boards. Any quick tips in our last minute here about how to really do that, um, practical level? Two things, um, board members really care about. They care about what their peers think about them inside the board. Right, so most people don't think of it this way. So when you go into the boardroom and you've done your homework and you've got the answer to every single question and I ask you a question as a board member and you answer it lightning fast, it signals that I just asked you a stupid question and now I look poorly in front of my peers on the board and I care deeply about what my peers think about me on the board. So feel the question. It's an interesting point. I hadn't thought about that before. This is an important topic. Here's my initial thinking. Field the question. I don't care how stupid you think the question is. Mind, feel it. And number 2, don't tell them everything you know. They're asking you a question. Answer the question. If there needs to be a supplementary question, somebody else will ask it or they'll ask a second question, because if you double down on your knowledge, of course you did your homework because you have good intent, but you tell them everything you know on the topic after you answered it quickly, you've doubled down on it was a stupid question and now that you're really making them look stupid in front of their peers and that, you know, they may not get you this board meeting, but they will get you. Thank you so much. This is really enlightening. Thank you, thank you.

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