Building Enterprise AI That Actually Works with Glean's Arvind Jain

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Aug 18, 2025

Arvind Jain, Founder and CEO of Glean and co-founder of Rubrik, shares insights on revolutionizing enterprise AI. He explains how Glean transformed from a search tool to a powerful conversational AI without pivoting. Arvind discusses the significance of customer relationships in competitive markets, the challenge of attracting talent from major tech firms, and the balance between innovation and product alignment in a growing team. He also delves into the delicate decision between remaining independent or considering acquisition as the company scales.

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INSIGHT

Search To Conversational Assistant

Glean began as enterprise search and naturally evolved as model capabilities improved.
Improved generation and reasoning let Glean synthesize answers, becoming a conversational assistant connected to company data.

ADVICE

Use Hype To Accelerate, Not Mask Weakness

Leverage market interest but focus on product readiness before scaling.
Use hype to accelerate growth only if you have a working product and customer traction.

INSIGHT

Search Is The Foundation For Enterprise AI

Search is the foundational infrastructure for enterprise AI and agent-building.
Because of that foundational role, major software companies are all trying to compete in the same space.

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Arvind Jain is the founder and CEO of Glean, building enterprise AI that connects to all internal company data, and co-founder of Rubrik, which recently went public. Starting as an enterprise search company in 2019, Glean has evolved into what Arvind calls "a more powerful version of ChatGPT inside your company," now approaching 1,000 employees and serving the world's most iconic companies.

What you'll learn:

How Glean evolved from search to conversational AI without pivoting by riding AI model capabilities
Why making it easy for customers to leave can be a competitive advantage in enterprise sales
The challenges of competing against every major software company building similar products
How to recruit from FAANG companies when you can't match their compensation
The difference between building for established markets vs. creating new product categories
Why enterprise buyers are tired of AI overpromising and prefer honest positioning
How to stay close to product development while scaling to 1,000 employees
The transition from Google engineer to startup co-founder and the skills you have to relearn
Why customer success and shared roadmaps are critical for complex AI implementations
The decision framework for staying independent vs. acquisition when building at scale

In this episode, we cover:

(00:00) Introduction to Arvind Jain and his journey from Rubrik to Glean

(01:27) Lessons learned building two different types of enterprise companies

(03:09) How Glean works as enterprise search and AI assistant

(06:00) The natural evolution from search to conversational AI

(08:00) Navigating the AI hype cycle and competitive landscape

(11:04) Competition strategy and staying ahead of major software companies

(16:40) Honest positioning vs. overpromising in AI sales

(20:01) Building enterprise reputation and customer relationships

(24:41) Motivation for continuing to build after previous success

(26:56) Staying close to product at scale and avoiding bottlenecks

(31:08) Using Glean internally and rapid iteration cycles

(32:18) The decision to stay independent vs. acquisition

(37:24) Transition from Google to startup founder

(43:45) Rapid fire questions and leadership lessons

(48:31) Uncomfortable feedback about constraining team speed