At VB Transform 2026, Zillow's engineering chief said AI ROI numbers only hold up if you measure before you build
The Avocado Pit (TL;DR)
- 🏗️ Zillow says AI ROI requires measurement before the build, not after.
- 🧠 Context, not just data, is crucial for real estate tech.
- 🔄 Centralizing AI tasks can cut costs and boost efficiency.
- 🔍 AI models need enterprise context for true value.
Why It Matters
Let's face it: AI promises to sprinkle fairy dust on your business problems, but without a solid plan, you're just adding glitter to chaos. At VB Transform 2026, Zillow's engineering maestro, Toby Roberts, spilled the beans on why measuring before building AI systems is like having a GPS before a road trip—essential if you don’t want to end up in the tech equivalent of a cornfield.
What This Means for You
If you're steering your own AI ship, remember that ROI isn't just an alphabet soup you can whip up post-launch. Lay down your measurement markers before you even start tinkering with AI. It's akin to baking a cake; you want to know if you have all the ingredients, not just hope it rises in the oven.
The Source Code (Summary)
At the VB Transform 2026 conference, Zillow's Senior VP of Engineering, Toby Roberts, emphasized that the company's AI success hinges on measuring success metrics before diving into technology development. This approach isn't about throwing data at the problem, but about maintaining context throughout the customer journey. Zillow's architecture avoids relying on a single chatbot to carry conversations across platforms, instead opting for a persistent context layer that follows customers seamlessly. Partnering with Glean, Zillow uses specialized AI models and centralized integration to streamline operations and cut costs.
Fresh Take
Zillow's strategy is a refreshing reminder that AI isn't magic; it's a tool that requires groundwork. By focusing on context and centralizing AI tasks, they're not just saving pennies—they're redefining the value AI brings to real estate. This isn't just about keeping up with the Joneses; it's about making sure your AI investment isn't a shot in the dark. So, before you jump on the AI bandwagon, take a page from Zillow's book: measure twice, build once.
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