At VB Transform 2026, Zillow's engineering chief said AI ROI numbers only hold up if you measure before you build

Zillow's SVP of Engineering, Toby Roberts, shared at VB Transform 2026 that AI's return on investment hinges on measuring its impact before implementation. The company struggles to maintain customer context across multiple interactions, which a chatbot can't manage alone. Roberts and Glean's CEO, Arvind Jain, discussed creating AI systems that can seamlessly carry context throughout the customer journey, highlighting the importance of upfront measurement for successful AI deployment. This insight underscores the necessity of strategic planning in AI to ensure it meets real-world needs effectively.