A week after OpenAI’s o3/o4-mini volleyed with Google’s Gemini 2.5 Flash, I sat down with Arvind Jain— ex-Google search luminary, Rubrik co-founder, and now CEO of Glean —just as his company released its agentic reasoning platform and swirled with rumors of a new round at a $7 billion valuation. We open on that whirlwind: why the model race is accelerating, why enterprises still gravitate to closed models, and when open-source variants finally take over. Arvind argues that LLMs should “fade into the background,” leaving application builders to pick the right engine for each task.

From there, we trace Glean’s three-act arc—enterprise search powered by transformers (2019), retrieval-augmented chat the moment ChatGPT hit, and now agents that have already logged 50 million real actions inside Glean enterprise customers. Arvind lifts the hood on permission-aware ranking, tool-use orchestration, and the routing layer that swaps Gemini for GPT on the fly. Along the way, he answers the hard questions: Do agents really double efficiency? Where’s the moat when every startup promises the same? Why are humans still in the review loop, and for how long?

The conversation crescendos with a vision of work where every employee is flanked by a team of proactive AI coworkers—all drawing from a horizontal knowledge layer that knows the firm’s language better than any newcomer.

If you want to know what’s actually working with AI in the enterprise, how to build agents that deliver ROI, and what the next era of work will look like, this episode is packed with specifics, technical insights, and bold predictions from one of the sharpest minds in the space.

Glean

Website - https://www.glean.com

X/Twitter - https://x.com/gleanai

Arvind Jain

LinkedIn - https://www.linkedin.com/in/jain-arvind

X/Twitter - https://x.com/jainarvind

FIRSTMARK

Website - https://firstmark.com

X/Twitter - https://twitter.com/FirstMarkCap

Matt Turck (Managing Director)

LinkedIn - https://www.linkedin.com/in/turck/

X/Twitter - https://twitter.com/mattturck

(00:00) Intro & Glean’s $7B valuation rumor

(02:01) The AI model explosion: open vs. closed in the enterprise

(06:19) Why enterprises choose open source AI (and when)

(10:33) The agent era: what are AI agents and why now?

(12:41) Automating business processes: real-world agent use cases

(16:46) Are we there yet? The reality of AI agents in 2025

(19:24) Glean’s origin story: reinventing enterprise search

(26:38) Glean agents: from apps to agentic platforms

(31:22) Horizontal vs. vertical: Glean’s strategic platform choice

(34:14) How Glean’s enterprise search works

(39:34) Staying LLM-agnostic: integrating new AI models

(42:11) The architecture of Glean agents: tool use and beyond

(43:50) Data flywheels and personalization in Glean

(47:06) Moats, competition, and the future of work with AI agents