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AI meets real estate, with Zillow's engineering SVP Toby Roberts artwork

AI meets real estate, with Zillow's engineering SVP Toby Roberts

GeekWire

September 19, 2026

On this week's show, recorded live at Atmosphere Seattle on the shores of Lake Union, Zillow Senior Vice President of Engineering Toby Roberts joins us to talk about what AI is doing to the business of buying and selling homes.

Speakers Toby Roberts, Todd Bishop, John Cook, Brittany Robinette

TopicsTech NewsNewsTechnology

Toby Roberts (0:00)

The home buying journey is the most expensive and one of the scariest transactions that people are gonna go through in their lives. Actually, like 50% of people cry during a home purchase. I mean, I'm sure, hopefully there's tears of joy, but there's a lot of tears of frustration in that, you know, at times.

If the AI agents are enabling real estate agents in terms of like doing a lot of that kind of fundamental blocking and tackling work that, you know, that the real estate agents are doing, they can spend more time focused on what is that human connection that has to kind of exist in this really scary transaction.

Todd Bishop (0:48)

Hello and welcome to GeekWire. I'm GeekWire co-founder, Todd Bishop.

John Cook (0:58)

And I'm GeekWire co-founder, John Cook.

Todd Bishop (1:00)

We are coming to you from Seattle, where we get to report each day about what's happening around us, in business, technology, and innovation. What happens here matters everywhere. And every week on this show, we get to talk about some of the most interesting and important stories and trends in the news. We are recording this week's show live on location at Atmosphere Seattle. It's an event venue here on the shores of Lake Union, in front of a room of real estate professionals and invited guests. We're here in partnership with Real Estate At Work. That is a meetup and professional networking group led by Leka Devatha, a Seattle real estate developer and broker.

Toby Roberts (1:40)

Yes.

Todd Bishop (1:43)

We've got a great crowd in the audience. It's a mixture of technologists and real estate professionals, coming up on this week's show AI meets real estate.

Seattle has been a key intersection for technology and real estate. In fact, we've been covering this mega story in the region for many years now. John, I feel like you broke this entire story back in the day.

John Cook (2:08)

Yeah, I set this multi-trillion-dollar industry on the path it's on. No, you're referencing, actually, I was looking back to one of my first stories I ever wrote at the Seattle Post Intelligencer where Todd and I worked a long time ago, a newspaper base here in Seattle. I was the first reporter to break the news that Rich Barton and Lloyd Frank were starting a new company out of Expedia. This company at the time, in fact, I said it was tentatively called zillow.com, so they weren't even sure on the name. But that was back in 2004, and the first headline was, former Expedia exec is back. Then a few months later, we had another story on the PI where it said, tight-lipped Zillow pulls in financing. We had a quote from Rich Barton at the time that said, we really think this thing can be big.

That's all he said.

Todd Bishop (3:00)

Well, that's the history. Tonight, we have a special guest to help us get our minds around what's next. Our guest is Toby Roberts. He's the Senior Vice President of Engineering at Zillow, where he's been for 10 years. He runs their core technology, the apps, the website, the data, the AI, with a team of about 650 engineers in the US, Mexico, and India.

He's the one who moves Zillow off its own servers and onto the cloud, and before Zillow, he worked at companies including Amazon, and Cox, and in electronic arts. Please welcome to the show, Toby Roberts.

Toby Roberts (3:36)

Thanks for having me. Great to be here.

John Cook (3:38)

Toby, great to see you and great to have you here with us for this conversation about where AI is meeting real estate. Something I bet you're thinking a little bit about these days.

Toby Roberts (3:47)

Every day.

John Cook (3:48)

Every day.

Toby Roberts (3:48)

Every day, over and over and over again.

John Cook (3:51)

Yeah. So Zillow was born 20 years ago, just celebrated your 20th anniversary.

Really, you came of age in the mobile era. Now, we're switching to a new technological era. That's right. Moving to the era of AI, or we're immersed in it in many ways. Just to start us off here, I'd love to hear your thoughts on how you feel AI is changing the way we find, buy, and sell homes.

Toby Roberts (4:20)

Yeah. I mean, it is a complete watershed moment, really. It has changed the full ecosystem, everything from how I understand what I'm even looking for, to understanding my financing options now, to really narrowing down where my search is, and really what's the type of home I'm looking for? Am I ready for renting, or am I moving from that rent to the buy scenario?

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