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

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