Did you ever stop and wonder how many hours you lose each week hunting for files, tabs, links, or half-written ideas scattered across your apps? It is a familiar frustration, and it sits at the center of today's conversation with Dropbox VP of Engineering, Josh Clemm. Josh has spent two decades building products shaped around scale, personalisation, and clarity, and he brings that mix of experience to Dropbox's push into AI and knowledge management.

In this episode, Josh shares stories from his time at LinkedIn and Uber, including the surprising Krispy Kreme promotion that took down Uber Eats across the globe and triggered a major rethink of architecture and resiliency. That experience shaped his belief that chaos often teaches the most. It also sets the stage for why he sees AI fluency as a leadership requirement rather than a trend.

You will hear how Dropbox is approaching internal experimentation, why context rot and work slop are real problems inside companies, and why the empty chat box often creates more anxiety than opportunity.

Josh walks through the thinking behind Dropbox Dash, a standalone AI powered knowledge layer that connects all of your cloud apps, understands their content, and turns search into something sharper and faster. He explains why context aware AI is the next leap, how Dash builds knowledge graphs across apps, and why the future of AI might look less like single player workflows and more like tools that sit inside the flow of teamwork.

It is a wide ranging conversation that moves from engineering history to the practical steps behind building AI products that feel useful rather than overwhelming. So here is the question that sits underneath everything Josh shared. What would your day look like if your information finally made sense without you having to chase it?

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Rosie Waterland

The AI-powered Podcast Player