Box CEO Aaron Levie joins Matthew Berman to discuss the real future of AI agents, the evolution of enterprise software, and why the job of the future isn’t doing the work—it’s managing the agents that do.

From bold takes on white-collar jobs to a deep dive into Box’s transformation into an AI-first company, Aaron Levie lays out one of the most compelling visions yet of how work will change in the age of AI.

Key Moments from the Interview

00:00 – The 50% Prediction
Why half of all white-collar jobs could disappear, and what comes next.

01:50 – What “AI-First” Really Means
Box’s strategy to expand capabilities, not just cut costs.

06:04 – How Box Deploys AI Internally
From Box Hubs to internal demos: building an AI-native company culture.

13:20 – Jevons Paradox for Labor
Why automation leads to more work, not less.

18:33 – Rethinking Work
AI flips the model: it’s not here to help you work faster, you’re here to make it productive.

22:55 – Managing the Agent Workflow
Why future jobs are about instruction, orchestration, and review.

31:00 – Memory, Portability, and Ownership
What happens when your agent knows you better than your coworkers?

35:47 – Agent Responsibility
Who’s liable when an agent screws up?

39:50 – The Real Bottleneck
Tech moves fast. People don’t. Change management is the drag coefficient.

43:20 – Who Owns the Agent Ecosystem?
Why there won’t be one winner—and why standards matter.

47:20 – The Application Layer Collapse
Does the SaaS UI disappear? Aaron agrees… sort of.

51:00 – Agents vs. Browsers vs. APIs
The future of the web might not have humans in the loop.

54:40 – Where Companies Get AI Wrong
Underestimating workflow change. Overestimating automation.

Full Interview: Aaron Levie on Agents, SaaS, and the Future of Work