Jay Thompson’s Journey to Zillow and Inman (Part 1)

We interviewed Jay Thompson, former Director of Industry Outreach with Zillow. Jay tells us about his Zillow journey including the things he did, dealing with haters, spreading Zillow’s mission, and what he thinks about Zillow’s plans.


About Jay Thompson

Jay is the former Chief Evangelist of Zillow where he worked there for six years. One of the brightest minds in real estate, Jay is a writer for his own blog as well as for Inman, the leading real estate news source for real estate agents, Realtors, and brokers.

It was in 2005 when Jay started a real estate blog with the domain phoenixrealestateguide.com. It blew up and got him on the map where he received a ton of business from. He and his wife then decided to start a small independent brokerage where they were getting more leads from the blogs.

Jay got licensed in 2004 when he was in Arizona. During that time in Arizona, you need to have a sales license for three years before you can sit for your broker’s license. After three years as a licensed sales agent, Jay took classes and got his broker’s license, and opened Thompson Realty.

Jay’s Time Before Zillow

Before real estate, Jay was in the semiconductor manufacturing industry in Austin at Motorola. In 2004-2005, there weren’t a ton of real estate blogs out there, but there were a few big ones in the Phoenix area. Jay was a relatively new agent that needed business. He thought that he can marry this love for writing and get some business out of it. It appealed to him, he was new in real estate and it was all new to him. He wrote about lenders and how real estate works. Jay also taught himself some SEO.

The SEO competition wasn’t that big, but Google was important. He never paid for Pay-Per-Click or Google Ads. It was all organic search results. His first goal was to make the blog rank number one on Google for the search term and then quickly realized that he got to the first page of Google after a year.

Despite ranking number one in the search results, the money wasn’t there. It was more of the overused hyperlocal things such as Gilbert Golf Course Homes as opposed to Phoenix Real Estate which is a big, broad, category. Those long-tail keywords are where the gold is and did much better-converting someone looking for golf course homes in Gilbert than someone that has randomly found him through Phoenix real estate.

Joining Zillow

Jay wrote about Zillow fairly often in his blog because it was in the news and Zillow launched in 2000. He wasn’t a Zillow fanboy and certainly was not a Zillow hater. He was kind of ambivalent. Jay knew that the company understands how to rank really well in search engines and they would put listing up there for free. He was very open to getting his listings out there on the internet for free not caring whether it be on Zillow, Realtor.com, his blog, or any other website. The more eyeballs on his listing, the better.

He continued to write about Zillow frequently on his blog because of the Zestimate which progressed to Agent Reviews which he is a fan of. The more Jay wrote about Zillow, the more he and the people from Zillow got to know each other. He quickly connected with Spencer Rascoff, who was the CEO of Zillow at that time. After making the connection over time, it grew into a good business relationship.

It was early 2012 when Zillow hired the CEO of the Arizona Regional MLS. Jay wrote a blog about Bob Bemis, the CEO. As a casual interviewer, he asked questions such as why are you going to Zillow, what’s going to happen to your spot, and tell us more about it.

Every time Jay wrote something about Zillow in his blog, he would always get a comment or a direct Twitter message from Spencer thanking him for writing about them. After a month of writing about Bob, Spencer wrote him back and told him to come to join the fun at Zillow.

Jay walked into the Zillow office in Seattle and he didn’t think that it would be a job interview. The HR handed him his scheduled and it showed that there were about 7 people interviewing him including the co-founders, Spencer, and the executives. Jay had no preparation for the interview. The interview went well and after a few weeks, they offered him a position.

It was a giant decision for Jay. He was a proud broker of a very successful brokerage in Phoenix with 30 agents and was profitable every month. They have also expanded their office in Tucson, Arizona where things were going great. Zillow kept calling him and Jay then accepted the opportunity and got hired as the Director of Industry Outreach.

The Intent of Zillow

A big part of Jay’s job ad the Director of Industry Outreach was reaching out to the industry. Another big part of his job that people didn’t see was letting people understand how real estate works. Zillow hires smart people most of them being young web developers, management, and salespeople. A lot of them didn’t have a lot of understanding of how real estate works. In the social space, Jay’s part was to respond to Zillow brand mentions particularly in the social space.

Zillow has changed so much since Jay left and what seemed to be primary amongst the Zillow brand detractors was the lack of understanding of what the company is doing. At the time it was needed to communicate better Zillow is plans and intentions where there was a lot of fear. 

It wasn’t because every hater was scared of Zillow, but there was fear, uncertainty, and doubt like there’s this big behemoth coming over the hill coming to take out jobs. It was a lot of baggage from the founder Rich Barton and Lloyd Frank who started Expedia. It got credit or blame for cratering the travel agent industry. There are still travel agents out there just like what people use real estate agents for.

The baggage is out there and originally Expedia really took it where the internet kind of crushed travel agencies and they’re going to do the same thing to real estate agents. That was never the intent of Zillow.

It leads people to question things hence the fear, uncertainty, and doubt about what are they doing and why are they doing it? When Jay worked for Zillow, he got death threats just because he worked for Zillow. It seemed crazy to him because why would you hate the person you don’t know simply because of who their employer is.

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Jay says that change is the only constant in life and in this industry. There are a bazillion very successful real estate people that have never given Zillow a dime, but you need to understand what it is that they offer and how to leverage it. Because if Zillow has one thing, whether you hate it or love them, you can’t argue that they have consumer eyeballs on their website and why not take advantage of that if you can. 

There are a lot of things you can do for free on Zillow. You can buy leads from them, but you’ve got to at least understand that Zillow, Realtor.com, Redfin, and OpenDoor, all these new people are not even new, but just change that’s come into the industry. You don’t necessarily have to use it but you sure better understand it.

Zillow Flex

When I was a premier agent with Zillow, I still had reservations about the platform. It was in February of 2021 when I became a flex agent and being part of Flex is they meet you once a week for six months and that experience was amazing for me.

Now, we meet every two weeks with my Zillow advisor, Todd. One of the things that taught me was Zillow is so smart at figuring out the kinks in a sales process from when a call comes in, meeting with who, to writing offers. Like in a traditional sales funnel, it’s not as dialed down. Zillow is not our only lead source, we also use another Ylopo product and they implement that to our other lead sources, and Todd, the advisor, has been really open and helpful.

I think that it’s a big fear that everyone has that at some point, Zillow could turn into a brokerage. I think that they realized that that’s not where it’s at. Of course, that could change but I just don’t see it happening with the way my interactions with them.

Will Zillow Become a Brokerage?

This is one of the biggest concerns that Jay has gotten as feedback when he worked for Zillow. He hasn’t worked for Zillow for almost four years and people still come out and attack him. They would say that he’s the guy that said Zillow will never be a brokerage and they went and got brokerage licenses and did the iBuyer thing. The iBuyer business is gone and shuttered.

Rich Barton, the co-founder and current CEO of Zillow said from his pre-Expedia days, he likes to take big swings, to use a sports analogy, you swing for defenses, and what happens to big homerun hitters in baseball, sometimes they connect and launch the ball out of the park, and sometimes they strike out. That’s just what happens when you swing bay.

Zillow Offers was a strikeout for Zillow and it’s rare, but it did happen. They didn’t put so much into that, but even during the iBuying cycle, you didn’t drive down the street and saw Zillow Realty signs on buildings and malls. They didn’t have offices or agents.

The reason Zillow got its first brokerage license during iBuying was that the state of Arizona’s Department of Real Estate said if you want to do this iBuying thing in Arizona, you need a brokerage license, and Jay came from the Arizona real estate market.

Zillow struggled for years to get good listing data for their site and they were making deals MLS by MLS across the country which involves negotiations and renegotiations and renewals. Jay thinks that someone at Zillow finally said that they’ve got a smattering of broker licenses for the pipeline thing and they can start pulling IDX feeds straight from the MLS where they can go have 700 listing suppliers to one.

Jay thinks that Zillow is going to be Zillow Realty where you see agents going in, working, and answering the phones. That’s not how that work. The big swing that Jay sees is the investment into the agents and the investment that he is putting into his firm as well as any other firm. For Jay, it’s the indicator that they’re going to keep it that way.

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