Super Data Science: ML & AI Podcast with Jon Krohn

951: Context Engineering, Multiplayer AI and Effective Search, with Dropbox’s Josh Clemm

Dec 23, 2025
In this engaging discussion, Josh Clemm, Vice President of Engineering at Dropbox, shares insights into Dropbox Dash, a revolutionary AI-powered universal search tool. He explains the concept of 'multiplayer AI,' emphasizing its role in enhancing collaborative work. Josh delves into the importance of context engineering, warning against 'context rot' that can diminish AI output quality. He also highlights lessons learned from building search apps and advocates for a balance between data-driven and intuitive decision-making in tech leadership.
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INSIGHT

Universal Search As The New Dropbox

  • Dropbox Dash is a universal search and context layer that ingests and organizes content across apps, not just Dropbox files.
  • Josh Clemm positions Dash as the critical first step for chat, answers, and future agentic workflows.
INSIGHT

Multiplayer AI Means Team-Aware Systems

  • Multiplayer AI means AI systems that understand multiple people, projects, and their connections, not just single-user assistants.
  • This enables collaborative workflows where the AI acts as a teammate across a team's shared data and tasks.
ADVICE

Bring AI Into The Browser

  • Embed AI into the browser so tools meet users where they work and capture page context and browsing history.
  • Use a side panel to combine page context with connected data sources for a powerful working set.
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