The Enterprise Context Wars: Tokens, Trust, and the Race for Relevance with Arvind Jain, Founder & CEO of Glean

What happens when finding a design document at Google is harder than finding anything on the entire internet? In this episode, Cameron Adams sits down with Arvind Jain, Founder and CEO of Glean, to unpack why enterprise knowledge was broken for decades and what it took to finally fix it. Arvind spent over a decade as a distinguished engineer at Google working on Search, Maps, and YouTube, then co-founded and led R&D at Rubrik, before a company-wide struggle to "find anything" inspired him to build Glean. Arvind traces the exact moment search and language models converged to make enterprise-wide understanding possible, and explains why he believes AI tools like Claude and ChatGPT are still too "brute force," burning tokens and time hunting for context that a well-built knowledge graph could deliver in one shot. They dig into the real economics of the AI boom, from budgets that vanish a month into the year, to the tradeoff CEOs are increasingly making between hiring more people and buying more tokens. The conversation turns candid on the messier realities of this moment too: the tens of thousands of half-built agents cluttering companies, the fine line between helpful AI-driven insight and workplace surveillance, and why Arvind pairs new graduates with veteran executives to reinvent business processes. He closes with the leadership lesson he can't stop repeating: you can't credibly ask your team to embrace AI until you've gotten your own hands dirty building with it first. Key Quotes “ Nothing about today's environment feels normal. The appetite for AI is unparalleled. There's never been any technology where enterprises feel as compelled as they do today that they have to bring these technologies in.” “You'll have to figure out what skills are being actively used,  where innovation is unconstrained. But then there are mechanisms to let people find the right things for themselves.” “You can have AI give you the first version of these skills, learning from the best people inside your company. You can make that same expert the owner of that skill and publish it in a company.” “ The more you know, the better you can manage your team members. It doesn't have to be seen as surveillance, but as your managers can help you more with all the insights that they have on you.” Timestamps 00:00 Introduction 01:38 The Prompt 04:00 Creative All Hands 07:00 1/3 of all employee time is wasted just trying to find information to do their jobs. 19:05 Annual AI budgets: Token costs are ballooning faster than anyone expected. 24:25 90% of enterprise AI users just ask occasional questions. Only 10% are power users. 27:35 Glean customers have built 30,000 to 40,000 internal agents. 35:27 Large enterprises are building digital clones of employees nearing retirement to preserve decades of expertise. 43:01 More insight means managers can support their teams better – without employees feeling surveilled. 47:14 Arvind and his chief of staff are automating away his role together. 48:05 Design Reveal 49:42 Rapid Fire Links Subscribe to the Prompted Newsletter: https://promptedwithcam.substack.com/ Cameron on LinkedIn: https://www.linkedin.com/in/themaninblue/ Arvind on LinkedIn: https://www.linkedin.com/in/jain-arvind/ Glean: https://www.glean.com/ The State of Marketing and AI Report 2026: https://www.canva.com/marketing-ai-report/?utm_medium=organic_social&utm_source=google_youtube&utm_campaign=b2b_dg_global-gen_awareness_pro_wbr_prompted-podcast-2026&utm_content=description-link&utm_term= AI Vision Sydney: https://www.canva.com/events/ai-vision-syd/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.