The Search Engine Behind Fortune 500s

Finding information in daily life is frictionless. A quick Google search pulls up restaurant reviews, historical facts, or the name of that actor from a movie you can’t quite place. But inside a company, finding the right information is far more complicated. Employees waste hours searching across disconnected platforms—emails, Slack messages, Google Drive folders, customer databases—only to come up empty-handed.

This inefficiency is more than an annoyance—it’s a productivity drain. Studies show workers spend nearly 20% of their week searching for information or the right colleague to ask. In large enterprises, where thousands juggle dozens of tools, this problem can cost billions in lost productivity. As companies grow, their knowledge base becomes increasingly fragmented, buried in emails, internal wikis, and forgotten Slack threads.

While consumer search engines have been refined over decades to deliver near-instant, relevant results, enterprise search has remained clunky, unintuitive, and siloed. Employees either struggle to find what they need or give up altogether, relying on colleagues to fill in the gaps—repeating questions, duplicating work, and slowing down decision-making.

This is the problem Glean is solving. By applying artificial intelligence to enterprise search, Glean enables employees to quickly surface the information they need—whether it’s a document, a presentation, or the name of a subject-matter expert—without digging through multiple applications. Rather than relying on keyword-based search, Glean understands context, intent, and permissions, ensuring that employees see only what’s relevant to them. As AI becomes a key productivity multiplier, Glean is positioning itself as a critical layer in how modern enterprises manage and retrieve knowledge.

Traction

Glean has emerged as one of the fastest-growing enterprise software companies, scaling its annualized recurring revenue to $100 million as of November 2024, a 203% year-over-year increase. Just ten months earlier, in January 2024, ARR stood at $39 million, itself a fourfold jump from $10 million in 2023. Such rapid growth is rare in enterprise software, where sales cycles are long, budgets are scrutinized, and adoption can take time. Glean’s trajectory signals strong demand for AI-powered search tools that solve a fundamental problem: finding information across fragmented enterprise software.

The company’s early traction came from fast-growing technology firms with 500 to 2,000 employees, where knowledge fragmentation often led to duplicated work and information silos across engineering, customer success, and product teams. Early customers included Databricks, Canva, and Confluent—companies generating and storing vast amounts of information but lacking a unified way to retrieve it. By 2024, Glean had expanded beyond the tech sector into financial services, telecommunications, retail, and healthcare, industries where knowledge discovery is equally critical. Today, the company serves more than 200 enterprise customers, including Duolingo, Grammarly, Webflow, Confluent, and T-Mobile.

To support its rapid expansion, Glean nearly doubled its workforce in 2024, growing from 337 employees in March to 614 by September. Hiring at this scale reflects both strong demand and the company’s investment in AI innovation and global expansion. With its move into industries like finance and healthcare, where security and compliance requirements are more stringent, Glean is positioning itself for long-term growth beyond its original base of technology firms.

While the revenue numbers are impressive, engagement tells an even more compelling story. Many enterprise SaaS tools struggle with adoption after purchase, with daily active user rates often languishing between 10 and 20 percent. Glean, by contrast, has achieved a DAU to MAU ratio of 40 percent as of September 2024, an unusually high level of engagement for enterprise software. Its AI-powered search assistant is used frequently, averaging five queries per user per day—on par with workplace Google Search activity.

Sustained adoption is as important as top-line revenue growth in evaluating a company’s long-term potential. Glean’s rapid expansion, deepening industry penetration, and strong user engagement suggest a product with staying power. The next challenge will be maintaining momentum as Glean scales into more complex enterprise environments. AI-driven search must now navigate increasingly stringent data privacy and security demands.

Milestones

• 2023: Glean reports $10 million ARR, primarily serving mid-sized tech firms.•

• January 2024: ARR reaches $39 million, a 4x increase in one year.

• March 2024: Employee headcount grows to 337, reflecting early expansion.

• Mid-2024: Glean expands into finance, telecom, retail, and healthcare, securing customers like T-Mobile, Grammarly, and Duolingo.

• September 2024: Workforce nearly doubles to 614 employees.

• September 2024: Raises $260 million Series E, reaching a $4.6 billion valuation.

• November 2024: ARR surpasses $100 million, marking a 203% year-over-year increase.

• Early 2025: Expansion continues into large-scale enterprise deployments in finance and healthcare.

• Mid-2025: Introduces advanced AI-driven workflow automation to strengthen enterprise adoption.

• Late 2025: Positioned as a potential IPO candidate, with industry speculation about a 2026 or later public offering.

Business Model

Glean generates revenue through a subscription-based model, delivering AI-powered search and knowledge management tools to mid-market and large enterprises. The company operates on a per-user licensing structure, with pricing that scales based on the size of the organization and the depth of integration required.

For mid-market companies, typically those with 500 to 1,000 employees, initial contracts range from $100,000 to $500,000 per year. Larger enterprise deals can exceed $5 million annually, particularly with Fortune 500 companies that require broader deployment across multiple departments. This pricing flexibility supports Glean’s land-and-expand strategy, where initial deployments in a single department often evolve into organization-wide adoption. A company might begin with a $60,000 contract for one department and scale to a $500,000 or even multimillion-dollar contract within a year as adoption spreads across the organization.

The company’s core value proposition is providing a unified search layer across an enterprise’s software stack. Employees in large organizations often struggle to find relevant information spread across various applications like Slack, Google Workspace, Microsoft 365, Salesforce, and Jira. Glean integrates with over 100 business applications, enabling employees to retrieve relevant information while respecting enterprise-grade data governance and permissions.

Unlike traditional enterprise search tools, Glean does more than surface documents. Its AI-powered assistant understands context, user intent, and role-based access to deliver personalized search results. For example, a customer support agent searching for troubleshooting documentation will see different results than an engineer looking for product specifications, even if they enter the same query. This adaptive approach reduces the time employees spend searching for information and improves workplace efficiency.

Glean’s go-to-market strategy focuses on selling to chief information officers and chief technology officers, who are responsible for enterprise knowledge management and IT infrastructure. The sales cycle for mid-market customers is typically around 90 days, while larger enterprise deals can take four to five months due to more complex security reviews and integration requirements.

One of Glean’s biggest competitive advantages is its deep understanding of enterprise permissions and governance. Unlike consumer search engines, which operate in an open environment, enterprise search must respect privacy controls, ensuring employees only see data they are authorized to access. Glean’s security model ensures compliance with corporate policies while maintaining high search relevance.

Opportunity

As enterprises adopt hundreds of SaaS applications, employees often struggle to locate information buried across platforms. The average large company now uses over 1,000 tools, but just 29 percent integrate smoothly, leading to nearly 20 percent of the workweek wasted on searching—costing businesses an estimated $1 trillion annually.

To solve this problem, Glean is capitalizing on several key opportunity areas:

AI-Powered Enterprise Search

The enterprise search market is projected to reach $13 billion by 2032, driven by the increasing complexity of workplace data. Traditional search tools rely on basic keyword matching, often failing to surface relevant information. Glean, in contrast, uses AI-driven semantic search, which understands context, intent, and user roles, ensuring employees receive personalized and permission-aware results.

As enterprises prioritize tools that improve internal knowledge retrieval, AI-based search solutions are expected to grow at the fastest rate within this market. Glean is well-positioned as one of the leading solutions capable of handling cross-platform enterprise search with deep integration into business systems.

AI Assistants and Workflow Automation

Beyond search, Glean’s AI assistant is evolving into a proactive workplace automation tool. Employees no longer just need to find documents—they need AI to analyze, summarize, and act on information. Glean’s assistant is moving toward handling repetitive tasks such as:

• Summarizing internal reports and conversations

• Providing contextual recommendations based on employee workflows

• Automating knowledge-based tasks like drafting responses or generating insights

Glean’s assistant is evolving beyond search and automation, setting the stage for more advanced enterprise AI capabilities in the future. The business process automation market is projected to grow to $19.6 billion by 2026, and Glean is well-positioned to capture this demand by integrating AI-powered automation into daily enterprise workflows.

Expansion into Highly Regulated Industries

Financial services and healthcare represent two of the most knowledge-intensive and regulation-heavy industries. Both rely on massive amounts of proprietary data, and professionals in these fields need secure, permission-controlled access to internal knowledge bases.

Glean has already begun expanding into these industries, where its strong security model and enterprise permissions expertise give it a competitive edge. As businesses in these sectors look for compliant AI solutions, Glean’s ability to respect access controls while delivering intelligent search capabilities positions it as a strong alternative to more generalized AI tools.

Global Expansion and Emerging Markets

Glean’s opportunity is not limited to the US market. The Asia-Pacific region is projected to be the fastest-growing market for enterprise search, with a CAGR of 13.8 percent through 2032. As international enterprises grapple with the same knowledge fragmentation issues as their US counterparts, Glean has the chance to expand into new geographies and build relationships with multinational corporations looking for AI-driven knowledge solutions.

Positioning for Long-Term Growth

Glean’s evolution from a search tool to a broader enterprise AI assistant signals its ambition to become an essential part of how businesses manage and access knowledge. By combining semantic search, workflow automation, deep enterprise security, and global expansion, Glean is positioning itself as a foundational layer of the modern enterprise.

The next phase of opportunity lies in expanding AI capabilities, integrating deeper with industry-specific workflows, and further strengthening security and compliance measures. As enterprises seek more intelligent, adaptive solutions for managing their knowledge, Glean has the potential to define the future of enterprise AI.

Competition

Enterprise search has long been a complex market, with many past attempts struggling to balance security, relevance, and usability. Many companies still rely on manual processes or disconnected search tools, making Glean’s biggest competitor the status quo—employees continuing to waste time searching across multiple platforms.

Despite increasing AI adoption, the market remains fragmented, with no single platform emerging as the definitive enterprise search leader. Glean competes across three categories: traditional enterprise search providers, AI-powered assistants, and enterprise knowledge platforms. Each offers distinct strengths and limitations.

Traditional Enterprise Search Providers

These companies focus on indexing and retrieving structured enterprise data, often within a specific ecosystem. While they have strong security and compliance features, they generally lack advanced AI-powered search capabilities and struggle to surface relevant cross-platform insights. Key players include:

• Microsoft SharePoint Search, which is a built-in enterprise search tool for Microsoft 365 but limited to content stored within Microsoft’s ecosystem.

• Google Cloud Search, designed for Google Workspace, with some third-party integrations, but lacks deep contextual understanding across different business applications.

• Amazon Kendra, an AWS-powered search tool that connects with internal enterprise databases but requires heavy customization and is not as user-friendly for employees.

• Elastic Enterprise Search, a developer-focused search engine that requires significant configuration and is often embedded into other applications rather than used as a standalone enterprise-wide solution.

AI-Powered Assistants and Workplace Search

This category consists of newer companies leveraging large language models to improve how employees search for and retrieve knowledge. While these tools often provide natural language search and chatbot-style interfaces, they typically lack deep integration into enterprise systems and struggle with security and permissioning at scale.

• Moveworks, an AI chatbot focused on IT and HR automation, allowing employees to search for help desk answers but not designed for full enterprise knowledge retrieval.

• You.com Enterprise, an AI-powered knowledge assistant that provides a ChatGPT-style interface for company-wide search but lacks deep enterprise system integrations.

• Guru, a knowledge management tool that helps teams store and retrieve knowledge, often embedded in Slack or browser extensions, but less suited for enterprise-wide search.

• Vectara, a generative AI search platform focused on developer-friendly API solutions, competing more with infrastructure-focused AI search tools than full-scale enterprise solutions.

Enterprise Knowledge Platforms

Some companies approach the knowledge problem from a collaboration and documentation perspective rather than pure search. While these platforms allow teams to organize and share information effectively, they are often not optimized for real-time AI-powered search across all enterprise systems.

• Notion and Confluence, which are powerful for team-based knowledge storage but require manual organization and lack AI-powered search beyond their own ecosystem.

• Microsoft Viva Topics, which uses AI to auto-tag and surface relevant content but is limited to Microsoft-based applications.

• Coveo, which specializes in customer service and ecommerce search rather than enterprise-wide knowledge retrieval.

• Lucidworks, which offers AI-driven search but primarily focuses on external-facing applications like ecommerce and customer support.

Glean’s Edge

What sets Glean apart is its deep integration across enterprise applications, AI-powered contextual search, and enterprise-grade security controls. Unlike traditional search providers, Glean is not limited to a single ecosystem like Microsoft or Google. Unlike AI chatbots, it offers deep system integrations that ensure results are secure, permission-aware, and actionable.

Glean is positioned as an enterprise-wide AI search and knowledge management tool rather than just a chatbot, help desk assistant, or document repository. Its biggest strength is indexing knowledge across an entire organization while ensuring employees only see content they’re authorized to access.

As AI-powered search gains adoption, Glean’s main challenge will be maintaining its technical and security lead while competing with companies that have deep distribution advantages, such as Microsoft and Google. However, its vendor-neutral approach, focus on enterprise security, and AI-driven knowledge graph provide a strong foundation for long-term differentiation.

Valuation and Investor Growth

Glean has attracted significant investor interest as it scales rapidly, securing over $600 million in funding since its founding in 2019. The company’s valuation has surged in parallel with its revenue growth, reflecting strong confidence in its long-term market potential.

In September 2024, Glean raised a $265 million Series E funding round at a valuation of $4.6 billion. The round was led by Altimeter Capital and DST Global, with participation from other major investors including SoftBank Vision Fund 2 and Coatue Management. These firms are among the most prominent names in venture capital, with track records of backing category-defining companies across enterprise software and AI.

What stands out in Glean’s fundraising history is the consistency of support from top-tier investors. Sequoia Capital, Kleiner Perkins, and Lightspeed Venture Partners have participated in multiple rounds—including the Series B, C, and D—underscoring their long-term confidence in Glean’s trajectory. This level of reinvestment from firms with deep enterprise AI expertise is a positive signal in a space where early-stage backers often exit as later-stage capital comes in.

Earlier rounds also showed accelerating momentum. Glean’s Series C in May 2022 valued the company at $1 billion, up from a $302 million valuation at its Series B just nine months earlier in September 2021. The company’s Series A, raised in June 2019, was priced at just $0.58 per share, marking a steep climb in value over the past five years.

With its latest funding, Glean has over $550 million in cash on hand, giving it ample runway to continue expanding its AI capabilities, deepen enterprise integrations, and enter new verticals such as financial services and healthcare. The company has also been investing heavily in global expansion, particularly in fast-growing markets like Asia-Pacific.

Looking ahead, Glean’s valuation trajectory suggests it could be a strong candidate for a public offering. If its growth continues at the current pace, an IPO in 2026 or beyond could be a natural next step, depending on broader market conditions. For now, investors are betting that Glean’s AI-powered search and knowledge management platform will become a foundational layer of enterprise productivity, setting it apart from traditional search providers and emerging AI competitors.

Pros and Cons

How to Invest

Glean shares are available on both secondary marketplaces and through private fund offerings, but inventory is currently limited.

Hiive currently has two active listings for Glean common shares. One listing is offering 2,600 shares at $50.00 per share, totaling $130,000. The second listing offers 7,000 shares at $52.00 per share, totaling $364,000. These listings are direct secondary sales, meaning investors purchase shares from existing holders without going through a fund structure.

Secondary pricing has steadily increased over the past six months, with Hiive’s aggregate Glean price now sitting at $47.18—a nearly 39% rise in half a year. The pricing trend reflects strong demand, with actual trade activity driving prices upward. However, supply remains tight, suggesting that many employees and early investors are holding onto their shares, likely due to confidence in Glean’s long-term potential.

Alternatively, UpMarket is offering Glean shares at $48 per share through a special purpose vehicle (SPV). This structure comes with additional fees, including a 6% subscription fee and a 1% annual management fee. There is also a 20% carried interest fee, which only applies to profits. In other words, Glean’s valuation would need to rise meaningfully—roughly by 20% or more—before investors see net gains after fees. While the implied valuation of approximately $6.6 billion is reasonable relative to Hiive’s secondary prices, the layered fees make this option more costly in the long run. However, for investors seeking exposure without waiting for direct secondary transactions, the UpMarket option may appeal to those optimistic about Glean’s upside and comfortable with the fund structure.

Overall, liquidity in the private market for Glean appears constrained. The limited supply on Hiive and the steady rise in secondary pricing suggest insiders are bullish, holding shares as the company eyes further enterprise expansion and a potential IPO in the coming years.

As with any private market investment, it is critical to review terms carefully, including fees, share type, and transfer restrictions. If you have questions about this opportunity or would like help evaluating the details, reach out to [email protected].

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