The Tech Blog Writer Podcast - Inspired Tech Startup Stories & Interviews With Tech Leaders, Entrepreneurs And Innovators

What does it actually take to move beyond AI pilots and turn enterprise ambition into real productivity gains? That question sat at the center of my conversation with Olivia Nottebohm, Chief Operating Officer at Box, and it is one that every boardroom seems to be wrestling with right now. AI conversations have matured quickly. The early excitement has given way to harder questions about return, trust, and what changes when software stops assisting work and starts acting inside it. Olivia brings a rare vantage point to that discussion, shaped by leadership roles at Google, Dropbox, Notion, and now Box, where she oversees global go to market, customer success, and partnerships at a time when AI is becoming embedded in everyday operations. We talked about why early adopters are already seeing productivity lifts of around thirty seven percent, while others remain stuck in experimentation. The difference, as Olivia explains, is rarely the model itself. Strategy matters more. Teams that treat AI as a chance to reth