a16z General Partner Martin Casado sits down with Box cofounder and CEO Aaron Levie to talk about how AI is changing not just software, but the structure and speed of work itself. They unpack how enterprise adoption of AI is different from the consumer wave, why incumbents may be better positioned than people think, and how the role of the individual contributor is already shifting from executor to orchestrator. From vibe coding and agent UX to why startups should still go vertical, this is a candid, strategic conversation about what it actually looks like to build and operate in an AI-native enterprise. Aaron also shares how Box is using AI internally today, and what might happen when agents outnumber employees. Timecodes: 00:00 Introduction to AI in the Enterprise 00:31 Aaron Levy, CEO of Box 01:32 AI in the Enterprise: Challenges and Opportunities 03:07 The Evolution of AI Adoption 04:54 AI's Role in Workflow Automation 05:55 Faster Buy-in Than Cloud: CIO Attitudes Have Changed 08:08 SaaS vs. AI-Native: Who Wins? 10:00 Is AI Just a Consumption Layer? 12:00 Business Models and the COGS of AI 15:00 New AI-First Categories Are Emerging 19:25 Box's Journey and AI Integration 21:39 The Future of Software and AI 27:41 AI in Decision-Making Processes 29:53 The Impact of Memo-Oriented Meetings 31:03 AI in Research and Strategy 32:18 AI's Role in Enterprise Budgets 43:03 The Future of Entry-Level Engineers 48:28 AI's Influence on Small Businesses 55:36 Predictions for the Next 5-10 Years Resources: Find Aaron on X: https://x.com/levie Find Martin on X: https://x.com/martin_casado Stay Updated: Let us know what you think: https://ratethispodcast.com/a16z Find a16z on X: https://twitter.com/a16z Find a16z on LinkedIn: https://www.linkedin.com/company/a16z Subscribe on your favorite podcast app: https://a16z.simplecast.com/ Follow our host: https://x.com/eriktorenberg Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures.