GLEAN

Arvind Jain knows a thing or two about search. He spent nine years at Google, where he worked on core search infrastructure before becoming an engineering director.

He left in 2012 to start Rubrik, a cloud data management company, which went on to be worth over $4 billion. So when he sat down to figure out his next move, he had a very specific frustration in mind.

At Rubrik, and at basically every fast-growing company, the same problem kept appearing: the company's knowledge was scattered across dozens of tools. Jira, Slack, Google Drive, Salesforce, Zendesk, Confluence, GitHub.

Everyone was drowning in information and simultaneously unable to find the thing they needed. New employees took months to become productive because they couldn't locate institutional knowledge.

Senior employees wasted hours searching for files they knew existed but couldn't surface.

Jain co-founded Glean in 2019 with T.R. Rajan, Piyush Prahladka, and Tony Gentilcore — all Google and Rubrik veterans.

The idea was straightforward: build a universal search layer that sits on top of all your enterprise tools, indexes everything with proper permissions, and lets employees find what they need in seconds. The founding team had built search systems at planet scale before.

They were going to apply that experience to the enterprise, where the bar for search had been embarrassingly low for decades.

Glean sells to companies, not individuals. The pitch is simple: your company already pays for fifty tools, but none of them talk to each other and nobody can find anything.

Glean connects to all of them — over 100 integrations including Slack, Google Workspace, Microsoft 365, Salesforce, Jira, Confluence, ServiceNow, GitHub, Zendesk, and more — and builds a unified, permissions-aware search index across all of it.

The critical word is permissions-aware. When an employee searches for something, Glean only shows them results they're actually allowed to see.

The engineering team doesn't surface HR salary documents. The intern doesn't see the board deck.

That sounds obvious but it's technically hard, and most previous enterprise search attempts got it wrong or just gave up and siloed everything.

Glean charges on a per-seat, subscription basis — enterprise SaaS pricing, typically sold through annual contracts. Deals tend to be large: the target customer is a company with hundreds or thousands of employees, each of whom benefits from search.

As companies expanded Glean's footprint from one department to the whole org, deal sizes grew accordingly.

Since 2023, Glean has expanded from pure search into a broader AI assistant platform. Employees can now ask natural language questions — 'What did we decide about the Q3 roadmap?' — and get synthesized answers drawn from across company knowledge.

It's moving from 'find the document' toward 'just tell me the answer,' which is a much stickier and more valuable product.

Glean Search is the core product — a unified search bar that indexes all your connected tools and returns relevant, permission-filtered results in real time. You type a name, a topic, or a phrase, and Glean surfaces documents, messages, tickets, emails, and more from across your entire company knowledge base.

It's significantly faster and more accurate than whatever native search exists in individual tools.

Glean Chat is the AI assistant layer built on top of that indexed knowledge. Instead of searching and clicking through results, you can ask natural language questions — 'What's our refund policy for enterprise customers?' or 'What did the product team decide about the API redesign last quarter?' — and Glean synthesizes an answer from actual company documents, with citations so you can verify the source.

This is where Glean is increasingly competing with Microsoft Copilot and Google Workspace's AI features.

Glean Agents allows companies to build custom AI workflows on top of Glean's knowledge graph. Think automated onboarding assistants, IT helpdesk bots, or sales enablement tools that can draw on company knowledge to answer customer questions.

It's Glean's move from individual productivity tool to platform — giving enterprises a way to build internal AI applications without starting from scratch.

Glean also offers a Developer API, letting companies embed Glean's search and retrieval capabilities into their own internal tools and applications. For engineering teams building internal platforms, this removes the need to rebuild the search infrastructure from scratch.

Glean's first advantage was its founding team. When you're selling enterprise software to large companies, credibility matters enormously.

Having a team of ex-Google engineers who built search infrastructure at scale is a very different opening conversation than a couple of MBAs with a PowerPoint. Customers trusted that Glean actually knew what they were building.

The second move was depth of integrations. Enterprise search had been tried before — Lucidworks, Elastic, even Microsoft's own search — but most competitors connected to a handful of tools and called it done.

Glean went to 100+ integrations. The message became: whatever you use, we connect to it.

That made Glean the default choice for companies running modern, fragmented tech stacks.

The timing with the AI wave was also fortunate in a way that felt earned. When ChatGPT exploded in late 2022, every large company's executive team suddenly wanted to know how to use AI internally.

Glean was already sitting on a permissions-aware index of all company knowledge — exactly the foundation you need to run an enterprise AI assistant safely. They weren't just a search company anymore; they were the infrastructure layer for enterprise AI.

The pivot was smooth because the foundation was already there.

Glean also grew through land-and-expand. They'd often start with one team inside a company — IT, engineering, customer support — prove value quickly, and then watch internal champions spread it to other departments.

The product sold itself once people started using it, because the problem it solved was universally felt.

The most obvious threat to Glean is Microsoft. Microsoft owns the productivity stack for most large enterprises — Outlook, Teams, SharePoint, Office 365 — and has been aggressively embedding Copilot into all of it.

If Microsoft's search and AI assistant becomes good enough, a lot of companies will ask: why are we paying separately for Glean when search is now included in what we already pay Microsoft?

Glean's answer is that Copilot only works well within the Microsoft ecosystem, while Glean connects to everything — Salesforce, Jira, Slack, Google Workspace, and the rest. For companies that live outside the Microsoft monoculture, or even for companies that use Microsoft alongside other tools, Glean is genuinely better.

But it's a real fight, and Microsoft has distribution, bundling power, and essentially unlimited resources to improve Copilot.

The second challenge is pricing. Enterprise AI deals are being scrutinized hard right now.

CFOs who signed up for exciting AI tools in 2023 are increasingly asking for ROI evidence. Glean is an efficiency tool — it saves employee time — but quantifying that in a way that justifies a meaningful seat-based contract isn't always easy.

Renewals are going to depend on whether companies can actually point to productivity gains, not just a feeling that search is better.

Third: the space is filling up with competitors. Notion AI, Confluence AI, ServiceNow AI, and a dozen point solutions are all adding AI search within their own products.

Glean's bet is that a neutral, cross-everything layer wins. That might be right.

But it requires constantly proving it.

Glean's investor list reads like someone handed a 'greatest hits of enterprise software investing' playlist to a DJ and said play everything.

Sequoia Capital led Glean's Series D in 2024, a $200 million round that valued the company at $4.6 billion. Sequoia has been involved since the early rounds — their backing was a signal to the enterprise market that this was a serious team building serious infrastructure, not another search startup that would fade in eighteen months.

Lightspeed Venture Partners was an early and consistent backer. Lightspeed has a long track record in enterprise software and understood exactly what Glean was building — they've seen enough enterprise infrastructure plays to recognize when the founding team and problem space genuinely align.

They also attracted some notable strategic and crossover investors as the rounds got larger. The inclusion of investors like Kleiner Perkins and General Catalyst alongside Sequoia gave Glean both capital and a network of enterprise customer introductions that pure financial investors can't provide.

The $1.8 billion total raised through 2024 is a lot of money for a search company. It reflects two things: first, that enterprise AI infrastructure is genuinely expensive to build at scale — the indexing, the integrations, the trust and permissions layer all require serious engineering investment.

And second, that investors believe the winner in enterprise AI search will be enormously valuable, and Glean currently looks like the most credible independent bet on that outcome.