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Box's Aaron Levie: Why SaaS still matters | Pioneers of AI

1.7K views· 3 likes· 42:35· Jan 14, 2026

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SaaS companies made work easier by revolutionizing enterprise software. But AI is starting to actually do the work for us. So what role do legacy SaaS platforms have in the AI era? Pioneers of AI sat down with Box CEO and co-founder Aaron Levie to discuss how his 20-year-old, 4 billion dollar company is back in startup mode to keep up with AI. Levie refers to the current moment as the third wave in Silicon Valley disruption following the dot com and app booms. He describes how Box is adapting to the rapidly evolving landscape, how AI is disrupting labor and software markets, and why SaaS still has value in this next chapter. Chapters: 00:00 Introducing Aaron Levie 01:21 Box’s origin story & Mark Cuban’s advice 08:22 Inside Box’s pivot to the cloud 11:06 The ‘magic’ behind AI 16:00 Is SaaS dead?? 19:16 Box’s pivot to agentic AI 26:32 How Box thinks about security for agents 29:27 Will AI replace workers? 35:55 Why to start a company now 40:05 What does it mean to be human in the age of AI? 🎧 LISTEN TO THE PODCAST Apple Podcasts: https://podcasts.apple.com/us/podcast/pioneers-of-ai/id1763085968 Spotify: https://open.spotify.com/show/6gbpjgcqJ40rtPrHnXeOWG 💻 LEARN MORE Our website: https://www.pioneersof.ai/ ⚡JOIN OUR COMMUNITY LinkedIn: https://www.linkedin.com/company/pioneersofai/ Facebook: https://www.facebook.com/pioneersofai Instagram: https://www.instagram.com/pioneersofai X: https://twitter.com/pioneersofAI TikTok: https://tiktok.com/@pioneersofai 💡ABOUT US Pioneers of AI is your guide to the latest technological frontier. Each week, host Rana el Kaliouby (AI scientist, investor, author, co-founder of Affectiva) is joined by the leading creators, critics, and thinkers behind mind-blowing technology and asks the important questions about how artificial intelligence is changing the way we live. As we venture together into the unknown, Pioneers is your tool to understanding and anticipating what comes next. #artificialintelligence #ai #technology #technology #machinelearning #ranaelkaliouby #pioneersofai #affectiva #aitechnology #futureofai #aiinnovation #aiadvancements #aiethics #aipodcast #aiinterview #techinterview #saas #saasdevelopment #futureofsaas #box #aaronlevie #futureoftech #futureoftechnology #software #softwaredevelopment #softwareasaservice #founder #founderstory #markcuban #entrepreneur #entrepreneurship

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