Wednesday, May 27, 2026

Former Zillow executives discuss AI and housing challenges

Former executives from real estate platform Zillow share their insights on AI and ongoing housing challenges. 

Zillow is widely recognised for transforming online home searches via a home search portal. Many former executives from Zillow have since gone on to create and lead new companies within real estate and technology sectors. 

“When you work at a company like Zillow or any of these great corporations, you have incredible scale and power, when you start something from scratch, no one cares – except for you, hopefully your teammates and your mom.”

Greg Schwartz, CEO and Co-Founder, Tomo Mortgage

Greg was the former President of Media and Marketplace at Zillow and described the adjustment from working at a large public company to starting a business from scratch.

He was required to recalculate his approach from being in a leading company already at scale with organisational support – in contrast to a smaller scale where any newly implemented idea would only be seen by a handful of people.

Luis Poggi, Co-Founder and CEO of the AI real estate agent assistant HouseWhisper, also reflected on lessons learned at his time at Zillow where he served as the company’s Vice President of product and engineering.

He recalled being encouraged early in his job to seek exceptional talent for job roles at the company rather than settling for adequate candidates, an experience and strategy which has helped him long-term when hiring. Also, with the emergence of AI, curiosity in new tech has changed what he values in future employees.

“A person who uses AI today can do the work of three or four or five people. I think the biggest constraint today is your imagination. Learn, test, try, fail. The only way a young, smaller company can compete with incumbents that have massive scale is to be faster”. 

Greg Schwartz, CEO and Co-Founder, Tomo Mortgage

Luis also recalls from his tenure at Zillow, trying to create a home improvement product before quickly moving to nix it. One of his biggest lessons was that home improvement, even in real estate, is a different industry and the diversion wasn’t helpful for his team.

“Most startups die for lack of focus, for distraction, not for competition. There was a big learning in how quickly we tried to do something too far – and then quickly killed it and focused on the core business. People are really suffering. Our kids are suffering – I think it’s pretty selfish that the industry is focused on this.”

Greg Schwartz, CEO and Co-Founder, Tomo Mortgage

Greg further suggests the industry as a whole has a distraction problem tied to the debate over private listings. He describes being a little discouraged that industry leaders are discussing exclusive listings in the middle of the housing affordability crisis in America.

Consulting Founder Jay Thompson, who previously was Zillow’s Director of Industry Outreach for roughly seven years said he developed what he calls ‘The High Road Philosophy’ during his time at the company.

“It’s a conscious thought process to go through when I deal with problems – whether they’re people or relationships. Be kind and be decent – to your teammates, your family, to your partners, your customers – rather than exercise conflict and power.”

Jay Thompson, Consulting Founder

Deviki Patel
Deviki Patel
Deviki is a Digital Journalist at AI PropTech News, Rental Living News and BTR News. She holds a BA (Hons) in Law and an LLM from the University of Leicester. Having transitioned from a background in property law, she brings a strong foundation in research and analytical thinking, supporting the delivery of well-informed, insight-led content across the Living and PropTech sectors.

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