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  1. Super Data Science: ML & AI Podcast with Jon Krohn
  2. 951: Context Engineering, Multiplayer AI and Effective Search, with Dropbox’s Josh Clemm
951: Context Engineering, Multiplayer AI and Effective Search, with Dropbox’s Josh Clemm

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

Super Data Science: ML & AI Podcast with Jon Krohn · Dec 23, 2025

Dropbox VP Josh Clemm discusses fixing enterprise search with Dash, pioneering 'multiplayer AI,' and mastering context engineering to win.

Enterprise Search Is Broken; A Universal Layer Is the Only Fix

The fragmentation of knowledge across 12-20 work apps renders individual search bars inefficient. A universal search tool like Dropbox Dash, which ingests and connects content from all sources, is necessary to restore productivity for knowledge workers.

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

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

Super Data Science: ML & AI Podcast with Jon Krohn·2 months ago

Engineering Leaders Must Use Side Projects to Stay Technically Grounded

To avoid becoming an "ivory tower" manager, engineering leaders should use side projects as a playground for new technologies. This practice ensures they understand the limitations of new tools like AI and can provide credible, concrete, hands-on guidance to their teams.

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

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

Super Data Science: ML & AI Podcast with Jon Krohn·2 months ago

Engineering Leaders Should "Farm" by Cultivating Inputs, Not Demanding Outputs

Effective engineering leadership is like farming: growth isn't achieved by demanding it from the plants. Leaders should obsess over inputs—clear goals, sound strategy, team structure, and operational rigor—to create the conditions for great engineering to happen naturally.

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

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

Super Data Science: ML & AI Podcast with Jon Krohn·2 months ago

"Multiplayer AI" Is About Team Context, Not Just Agent Collaboration

The next frontier for AI isn't just personal assistants but "teammates" that understand an entire team's dynamics, projects, and shared data. This shifts the focus from single-user interactions to collaborative intelligence by building a knowledge graph connecting people and their work.

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

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

Super Data Science: ML & AI Podcast with Jon Krohn·2 months ago

Over-reliance on A/B Testing in Big Tech Creates Organizational Lethargy

In large companies, a culture of A/B testing every decision can become a crutch that stifles innovation and speed. It leads to risk aversion and organizational lethargy, as teams lose the muscle for making convicted, gut-based decisions informed by qualitative customer feedback.

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

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

Super Data Science: ML & AI Podcast with Jon Krohn·2 months ago

Browser-Embedded AI Will Reshape Knowledge Work by Meeting Users Where They Are

For many knowledge workers, the browser is their primary IDE. AI tools that operate as embedded extensions can leverage the real-time context of a webpage, combine it with a user's broader work data, and provide powerful, in-the-moment assistance without forcing a context switch.

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

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

Super Data Science: ML & AI Podcast with Jon Krohn·2 months ago

Enterprise AI Search Requires a Hybrid of Lexical and Vector Retrieval

Vector search excels at semantic meaning but fails on precise keywords like product SKUs. Effective enterprise search requires a hybrid system combining the strengths of lexical search (e.g., BM25) for keywords and vector search for concepts to serve all user needs accurately.

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

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

Super Data Science: ML & AI Podcast with Jon Krohn·2 months ago

"Context Rot" Degrades AI Quality; Bigger Context Windows Aren't Better

Even models with million-token context windows suffer from "context rot" when overloaded with information. Performance degrades as the model struggles to find the signal in the noise. Effective context engineering requires precision, packing the window with only the exact data needed.

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

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

Super Data Science: ML & AI Podcast with Jon Krohn·2 months ago

RAG Is Evolving From Single-Shot Retrieval to Multi-Step Agentic Workflows

Classic RAG involves a single data retrieval step. Its evolution, "agentic retrieval," allows an AI to perform a series of conditional fetches from different sources (APIs, databases). This enables the handling of complex queries where each step informs the next, mimicking a research process.

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

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

Super Data Science: ML & AI Podcast with Jon Krohn·2 months ago

Ground AI in Deep Work Context to Combat Plausible-Sounding "Work Slop"

AI-generated "work slop"—plausible but low-substance content—arises from a lack of specific context. The cure is not just user training but building systems that ingest and index a user's entire work graph, providing the necessary grounding to move from generic drafts to high-signal outputs.

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

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

Super Data Science: ML & AI Podcast with Jon Krohn·2 months ago