Zillow’s Senior VP of Engineering, Toby Roberts, alongside Glean CEO Arvind Jain, shared insights at VB Transform 2026 about building AI architectures that maintain customer context throughout extended real estate journeys. Zillow integrates AI deeply into processes touching 80% of U.S. real estate transactions annually, emphasizing that tracking customer context—not just data—proved to be the biggest challenge. They developed a proprietary context layer to ensure seamless experience across various interaction points, rejecting reliance on single chatbots or general AI models. Instead, Zillow utilizes specialized AI models and works closely with Glean’s platform to centralize integrations and control costs. Key takeaways include setting a measurement baseline before AI implementation, centralizing context management, enforcing strict permission protocols for sensitive data, and treating context management as a cost-saving strategy rather than simply a feature.
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