“I’m just finding more stuff to have the AI do — and then I end up doing more work as a result.”
That’s how Box CEO Aaron Levie sums up the paradox of generative AI at work: it saves time, and uncovers infinitely more stuff to take on.
On this week’s GeekWire Podcast, we catch up with Levie for our first in-depth conversation since GeekWire Startup Day in 2012. In some ways, it feels like a completely different world — and in others, not much has changed. Levie is still thinking about how technology reshapes work, how startups scale, and how to stay ahead of the next big shift.
We talk about Box’s new suite of enterprise AI agents, its integration with Microsoft Copilot, and why Levie says we’re still at the very beginning of figuring out how these tools fit into real work.
“We are on day one of agent adoption in the enterprise,” Levie says, describing 2025 as a year of pilot projects and experimentation. If you ask 10 people to describe AI agents, he says, you’d probably get 20 times the number of use cases than are realistic today.
At the same time, he said, some early use cases for Box’s new AI agents are already proving valuable for customers — such as extracting key information from contracts and organizing it into a structured database; or analyzing large volumes of internal data to help generate product recommendations or due diligence reports.
Levie talks about how AI is changing the way he works, as part of Box’s push to be an AI-first company. He uses AI tools and agents to write documents and strategy plans, research market trends and customer data, review and improve content, summarize internal materials, and build early versions of product ideas and prototypes.
But for the time being, at least AI is not drafting his social media posts.
“I write my tweets, I write the LinkedIn posts,” he explains. “It’s sort of a self-discipline of ensuring that I understand the topic and the subject. … Understanding things deeply means you’ll use better judgment when you come across that thing in the wild.”
Founded in 2005 by Levie and his fellow Mercer Island High School alum Dylan Smith, Box began as a simple file-sharing service and has evolved into a platform for what it calls intelligent content management. It went public in 2015 and has about 2,800 employees, with more than $1 billion in revenue last year and nearly $245 million in profits.
Even with all that growth, Levie says Box feels more like a startup than it has in years. He explains what he’d tell his 2012 self about the long game of building a company.
“It doesn’t get easier,” he says. “That moment doesn’t really happen. And if it does, it’s very fleeting, like six months.”
He explains, “There’s a window where things feel like all the pieces have been put in place, and then, boom — something happens in the economy, or the macro, or geopolitically, or now obviously directly in the tech space, and the whole chessboard just gets flipped upside down.”
Then it’s “back to figuring out where the pieces are,” he says. “And then you just go and grind again.”
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