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Home » This Box VP Loves Candidates With Side Projects, and Has One Himself
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This Box VP Loves Candidates With Side Projects, and Has One Himself

EditorBy EditorOctober 22, 2026No Comments3 Mins Read
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Knowing how to use AI is only enough to get a foot in the door for interviews, according to a Box executive.

Rand Wacker, Box’s vice president of product strategy, said that for candidates applying for a job at Box, AI literacy is a bare-minimum requirement. Having a fully developed side hustle or project — something he practices himself — is what gives potential hires a leg up in interviews.

Case studies, which he said used to be a staple in Box interviews, are now a relic of the past. Now, he expects candidates to be prototyping out their ideas.

What he really likes to see is candidates showing him a product they’ve built themselves using AI, even if it has nothing to do with Box’s business. He said he’s had potential hires show him mobile apps that they’ve built, gotten onto the App Store, and are monetizing to some degree.

“They’re running this little side hustle overall,” he said. “And it shows the passion.”

He said that people who explore and experiment with AI are the ones who win in the AI world, as they figure out how to use it most effectively in their personal and professional lives.

He practices what he preaches

Wacker, who’s spent almost 30 years in the software engineering and product management fields, said he started out as a “computer nerd” and loved playing around with software tools and building things.

As he progressed in his career, he said he had less time to experiment with building, but AI has recently allowed him to test small ideas he didn’t have time to explore before vibe coding existed.

He recently made an app to bring back old-school TV because he missed the days when he’d turn it on, pick one of three cable channels, and it would play a random movie from a random point.

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“These days, whenever I’m trying to find something to watch on the weekends, it’s decision fatigue. Which of the six streaming services do I go to? What are the 20 million titles I scroll through?” he said.

Using Cursor, he built an Apple TV app that would access his entire movie library, pick a random movie, and play it from a random point.

Working on these kinds of projects is a great way to learn the tools available on the market, get ideas for how to use them in other areas, and scratch the itch to create something of his own.

Wacker is one of many executives who have dipped their toes back into building and writing code in recent years. Leaders who haven’t written lines of code in decades have started experimenting with AI coding to stay closer to their products and feel like individual contributors.



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