At the time, Zillow was capturing only 15% of rental listings while Craigslist dominated with 60% market share. The rental market represented a $50B opportunity. The design challenge wasn't features—it was trust. Landlords defaulted to Craigslist not because it was better—because it was familiar. Zillow had brand recognition with renters. But landlords saw Zillow as a search tool, not a management platform. To win the rental market, we needed to earn landlord trust—which meant building tools that felt essential, not optional.