Zendesk just announced the acquisition of Unleash, an Israeli AI‑powered enterprise search startup with 70+ connectors to things like Google Drive, Confluence, and SharePoint. The pitch is “permission‑based RAG” and AI agents that live inside Slack and Microsoft Teams.

Sound familiar? It should. That’s basically what Glean does.

But is Zendesk really trying to compete with Glean?

Not directly. And here’s why the nuance matters if you’re a founder or investor in this space.

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First, Let’s Talk About What Glean Actually Is

Glean is on an absolute tear:

• $7.2 B valuation as of June 2025 (up from $4.6 B just 9 months earlier)

• $200 M+ ARR estimated as of November 2025, up from $100 M at fiscal year‑end January 2025

• 800+ employees

• 100+ SaaS connectors (Google Workspace, Microsoft 365, Slack, Salesforce, etc.)

• Enterprise knowledge graph that personalizes search results per user

• AI Agents platform powering 100 M+ agent actions annually

Glean’s core value prop: Your company has knowledge scattered across 50+ SaaS apps. Employees waste 13+ minutes per search trying to find stuff. Glean creates a unified AI‑powered search layer across everything, with proper permissions baked in.

Customers: Databricks, Canva, Confluent, Duolingo, T‑Mobile. Initial ACVs of $100 K–$500 K, with Fortune 500 deals exceeding $5 M annually.

This is a horizontal enterprise‑search play. Search everything. For everyone. Across the whole company.

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What Zendesk Is Actually Doing

Zendesk’s acquisition of Unleash is different. This is about employee service, not general enterprise search.

“As organizations rapidly adopt AI, rethinking how they deliver internal employee support is becoming mission‑critical. Zendesk’s acquisition of Unleash puts AI directly in the flow of work, delivering secure, permission‑based answers from across company systems so employees get instant self‑service with seamless handoffs to human experts when needed.”

— President of Product, Engineering and AI, Zendesk

Translation: This is about IT help desks, HR service desks, and internal support tickets—not about helping your marketing team find that Q3 strategy deck.

Zendesk’s play:

1. Own the employee service workflow end‑to‑end – case management → AI search/RAG → ticket routing → resolution analytics

2. Deploy AI agents in Slack/Teams that answer common employee questions before a ticket is even created

3. Reduce internal support costs while improving response times

This is a vertical application of enterprise search—search for employee support within the context of service tickets, with escalation paths built in.

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Why This Matters: The Bundling vs. Best‑of‑Breed Battle

Glean’s vulnerability: It’s a standalone product that competes on being the best at one thing (enterprise search). As Microsoft, Google, and now Zendesk bundle AI search into their existing platforms, Glean must prove its separate purchase is worth the extra effort.

Zendesk’s advantage: They already own the customer‑service and (increasingly) employee‑service workflow. Adding AI‑powered search makes their existing product stickier—no separate procurement, no separate security review, just “turn on this feature.”

Classic platform bundling playbook

• Salesforce bought Slack, then added AI search capabilities

• Microsoft has Copilot embedded everywhere

• ServiceNow has been building this for IT service management for years

• Now Zendesk does it for customer + employee service

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The Numbers Tell the Story

| Metric | Glean | Zendesk (with Unleash) |

|--------|-------|------------------------|

| Valuation | $7.2 B | $2 B (revenue) |

| ARR | $200 M+ | — |

| Connectors | 100+ | 70+ (via Unleash) |

| Focus | Horizontal enterprise search | Vertical employee‑service search |

| GTM | Standalone SaaS | Bundled into Zendesk platform |

Zendesk isn’t trying to beat Glean at general enterprise search. They’re trying to make Glean irrelevant for the employee‑service use case by bundling comparable functionality into their platform.

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What Zendesk Has Been Building in AI

This is Zendesk’s 5th AI‑focused acquisition in 18 months:

1. Klaus (Jan 2024) – AI‑powered QA and coaching

2. Ultimate (Mar 2024) – AI agents for customer‑service automation

3. Local Measure (May 2025) – AI‑powered voice/contact‑center

4. HyperArc (Jul 2025) – GenAI‑powered analytics

5. Unleash (Dec 2025) – Enterprise AI search

The pattern is clear: Zendesk is assembling an AI‑native service platform piece by piece. The thesis is that AI will transform how companies handle both customer and employee support, and Zendesk wants to own both workflows. Unleash is the knowledge‑retrieval layer that makes all the other pieces smarter.

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Why Unleash?

Unleash (unleash.so) is a Tel Aviv‑based startup. Founder Itay Itzhaki has a cybersecurity background and previously built and sold a startup. Key capabilities:

• 70+ enterprise connectors (Google Drive, Confluence, SharePoint, Slack, etc.)

• Permission‑based RAG (respects who can see what)

• Native AI agents for Slack and Microsoft Teams

• Built‑in handoff to human experts

• SOC 2 Type II certified, GDPR compliant

For Zendesk, this solves the “cold‑start” problem. Building 70+ connectors from scratch would take years. Buying Unleash gets them immediately competitive on the connector count that matters for enterprise sales.

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The Bigger Picture: Everyone Wants to Own the AI Knowledge Layer

Pure‑play enterprise search

• Glean (standalone)

• Perplexity (launching enterprise search)

• Coveo, Sinequa, Lucidworks (legacy players)

Platform bundlers

• Microsoft (Copilot everywhere)

• Google (Gemini Enterprise + Agentspace)

• Amazon (Q for Business + Quick Suite)

• Salesforce (Einstein + Data Cloud)

• ServiceNow (Now Assist)

• Zendesk (now with Unleash)

Every major enterprise platform is trying to embed AI‑powered knowledge retrieval into their workflows. The question for pure‑play vendors like Glean is whether being best‑of‑breed is enough when “good enough” comes bundled for free.

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What This Means for Founders

If you’re building in enterprise search

• The market is fragmenting into horizontal (Glean) vs. vertical (platform‑bundlers)

• Expect platform vendors to bundle “good enough” search into their products

• Differentiate by being dramatically better or by serving a workflow they don’t touch

If you’re building AI agents for employee service

• Zendesk is now a much more formidable competitor

• Their stack: AI search (Unleash) + AI agents (Ultimate) + QA/coaching (Klaus) + voice (Local Measure) + analytics (HyperArc)

• Your wedge needs to be really sharp

If you’re evaluating enterprise search for your company

• Evaluate not just features but entire workflows

• If you’re already a Zendesk shop, see what they bundle before buying Glean

• For a horizontal, company‑wide search layer, Glean remains the leader

• For employee‑service‑specific search, Zendesk’s integrated approach may be more valuable

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The Bottom Line

Is Zendesk building a Glean competitor?

Kind of, but not really. They’re building a Glean‑equivalent for the employee‑service use case, bundled into a platform that already owns that workflow. It’s not trying to replace Glean for general enterprise search across the whole company; it’s trying to make Glean unnecessary for IT and HR service desks.

This is the classic platform vs. point‑solution battle. Glean must prove its standalone value is worth the extra purchase. Zendesk must prove its bundled solution is “good enough.”

My take: Glean is safe at the high end for now. But the middle market—companies with 500–2,000 employees who don’t need Glean’s full horsepower—may increasingly just use whatever their service platform provides. That’s where Zendesk is playing. With $2 B in revenue and an aggressive AI M&A strategy, they’re not messing around.