Are we in the iPhone moment of AI, or are we still building janky mobile apps? Box CEO Aaron Levie brings 15+ years of enterprise software experience to break down the biggest questions facing SaaS companies today. From pricing models to regulatory risks, this conversation goes deep on what's actually happening behind the AI hype.

The Great AI Pricing Experiment

Every software company is scrambling to figure out how to monetize AI agents. Do you charge by seats, tokens, outcomes, or some hybrid model? Levie reveals the chaos happening in boardrooms:

"There's no board of directors in software that is not making this the number one topic of every board meeting."

The challenge isn't just technical - it's existential. Companies are making architecture decisions in a vacuum, and there's a high probability many will get it wrong.

Why AI Layoffs Could Backfire Spectacularly

Here's where things get controversial. Levie warns that tech leaders using AI as cover for regular performance management are setting the industry up for regulatory disaster:

"People like Bernie Sanders will then totally jump on that. And so we as an industry are doing ourselves a disservice when we kind of over prop up that message because that's actually the surest path to over regulation of this technology."

The Productivity Paradox: Why AI Made Box Hire MORE Engineers

Forget the cost-cutting narrative. Levie shares how Box's AI implementation led to hiring more people, not fewer:

"If we can accelerate our product roadmap, that actually encourages us to hire even more engineers, because now we have higher productivity in this part of the organization to deliver even more value."

The key insight? Companies focused on output expansion rather than cost reduction will dominate their markets.

The Oracle Reality Check

In a moment of refreshing honesty, Levie admits his past predictions about "obvious" disruptions were dead wrong:

"You live long enough to see Oracle as a $600 billion company. When you're naive, you would have said, well, everything's obviously moving to SaaS and this business is going to get totally disrupted. You're constantly reminded that Larry Ellison's the G.O.A.T."

This humility shapes his contrarian take on AI disruption.

Will AI Kill Salesforce? The Surprising Answer

Levie's boldest prediction: traditional SaaS platforms will coexist with AI rather than be replaced by it. He compares it to how movies and TV coexisted rather than one killing the other:

"I look forward to replaying this in 10 years and it might be so laughably wrong, but just think about other paradigms, right? When movies came out, when TV came out, it coexisted with movies."

The Architecture That Matters: Church and State

On the technical side, Levie argues for strict separation between AI agents and core business data:

"I think you really do need to have a separation of duty or a church and state between what the agent is doing and the underlying object model, data model, or kind of business process."

The risk? Non-deterministic AI systems corrupting your deterministic business data.

The Final Word on AI Strategy

Levie's closing advice cuts through the noise:

"Everybody should be thinking about AI agents for expanding the capability of their software and their organization. And when you have that kind of prism in which you execute, you will find 10 times more interesting things to do than just replacing some kind of cost center."

This episode is essential listening for anyone trying to understand how AI will actually reshape enterprise software - beyond the hype and fear-mongering.

Companies Mentioned:

Box
Oracle
Salesforce
ServiceNow
Workday
Microsoft
Meta
Dropbox
DocuSign
Glean
Conga
Snowflake
Airtable
Intercom
Linear
Asana
Atlassian
ChatGPT/OpenAI

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S2E10: Why AI Won't Kill Salesforce | Aaron Levie (Box)

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