Show notes
In 2024, OpenAI asked its own investors to avoid funding five companies it saw as competitive threats: Anthropic, Elon Musk's xAI, Ilya Sutskever's Safe Superintelligence, the search engine Perplexity, and one enterprise AI company, Glean. Arvind Jain built Glean after a decade as a distinguished engineer at Google and after co-founding the data security company Rubrik, starting it in 2019, years before most of the world had heard of generative AI.
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Glean is now valued at $7.2 billion, generates more than $300 million in annual recurring revenue, and employs roughly 1,500 people, one of the largest pure-play enterprise AI companies in the world. Its bet is that enterprises don't need Glean to build its own frontier model. They need it to be the context and intelligence layer that plugs into whichever model, Claude, GPT, Gemini, or an open source one, actually gets the job done.
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In this conversation, Arvind walks through why he doesn't believe AI will let companies meaningfully shrink their workforce, even as it reshapes what people do all day. How Glean's own leaders, not just its engineers, are required to build their own AI agents, no exceptions. And why, after seven years running one of the most AI-native companies in the world, the feeling of having "arrived" still hasn't shown up.
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Arvind Jain is the founder and CEO of Glean, an enterprise AI platform valued at $7.2 billion that he founded in 2019 after spending more than a decade at Google as a distinguished engineer, leading teams across Search, Maps, and YouTube. Before Glean, Jain co-founded Rubrik, the publicly traded cloud data security company, where he led R&D. Glean has raised more than $765 million from investors including Sequoia Capital, Kleiner Perkins, Lightspeed Venture Partners, ICONIQ, and Wellington Management, most recently a $150 million Series F in June 2025. In 2024, OpenAI reportedly asked its own investors not to fund Glean, placing it on a list alongside Anthropic, xAI, and Safe Superintelligence. Jain holds a BTech in computer science from the Indian Institute of Technology, Delhi, and a master's in computer science from the University of Washington.
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Where to find Arvind Jain:
• Glean
• X
• LinkedIn
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Where to find Nakul:
• Audacious Ventures
• X
• LinkedIn
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Where to find Audacious Ventures:
• Website
• LinkedIn
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In this conversation with Arvind Jain:
00:00 Who is Arvind Jain?
01:56 What is Glean's edge as OpenAI, Google, and Notion pile in?
04:56 MCP vs. context graphs: why did Glean go its own way?
07:56 What structural advantage does Glean claim over the frontier labs themselves?
11:00 How does Glean stack up against AI-native platforms like Notion?
12:38 What happens to the SaaS stack by 2027 and 2028?
14:52 Is Glean an app, an agent platform, or core infrastructure?
19:22 How much of Glean's use today is questions versus real agent work?
20:52 What does a knowledge worker's life look like in three years?
24:08 Why doesn't Arvind think AI will let companies shrink their workforce?
27:32 How does Arvind self-serve strategy, talent, and customer insight with AI?
33:19 Is every department at Glean AI-native, not just engineering?
36:44 What did Arvind find flawed in the AI SDR dream?
38:19 How has AI reshaped hiring at Glean, and who thrives there now?
41:07 Are Glean's 1,500 employees secretly doing the work of 2,500?
41:55 Why does Arvind say you never feel like you've "arrived"?
45:38 What's Arvind's advice for anyone who wants his life?
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Arvind's sharpest lines from this conversation:
On why headcount survives AI:
"Ultimately, the business success is indeed proportional to the human capital that you have inside the company."
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On AI closing the skill gap:
"Take a calculator. Does everyone know how to use it today equally well? I think that's what's gonna happen with AI."
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On the real job of a CEO:
"As a CEO, most of my job is understanding, and I think these are actually harder problems, frankly."
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On AI SDRs and human judgment:
"AI should be used as a tool, not something that replaces the entire human task. It can replace 90% of the task."
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On spotting AI-written text:
"My high school kids can tell you very quickly what text is written by AI and which one is not."
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On why nothing feels defensible now:
"Everything that you build, instead of it feeling like your moat or your IP, sometimes it feels like a liability, because you have to quickly get rid of it."
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On what AI still can't do:
"AI is not capable of replacing you right now. Let's be clear, it's not ready to replace even a single human today, no matter what job they do today."
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On advice for someone starting out:
"Work very, very hard until the very last day. You'll be building connections with the people who've worked with you, and your impressions always carry forward. That's the one that actually gives you those rewards."
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