In its 20-year history—Zillow celebrated the anniversary this week—the company has always used AI. Wacksman, who joined in 2009 and became CEO in 2024, notes that machine learning is the engine behind those “Zestimates” that gauge a home’s worth at any given moment. Zestimates became a viral sensation that helped make the app irresistible, and sites like Zillow Gone Wild—which is also a TV show on the HGTV network—have built a business around highlighting the most intriguing or bizarre listings.