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.
First, Let’s Talk About What Glean Actually Is
Glean is on an absolute tear:
- $7.2B valuation as of June 2025 (up from $4.6B just 9 months earlier)
- $200M+ ARR estimated as of November 2025, up from $100M 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 100M+ 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.
The customers? Databricks, Canva, Confluent, Duolingo, T-Mobile. Initial ACVs of $100K-$500K, with Fortune 500 deals exceeding $5M annually.
This is a horizontal enterprise search play. Search everything. For everyone. Across the whole company.
What Zendesk Is Actually Doing
Zendesk’s acquisition of Unleash is different. This is about employee service, not general enterprise search.
Here’s the key quote from Zendesk’s President of Product, Engineering and AI:
“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.”
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 here is:
- Own the employee service workflow end-to-end: Case management → AI search/RAG → ticket routing → resolution analytics
- Deploy AI agents in Slack/Teams that answer common employee questions before a ticket is even created
- Reduce internal support costs while improving response times
This is a vertical application of enterprise search. Search for employee support. In the context of service tickets. With escalation paths built in.
Why This Matters: The Bundling vs. Best-of-Breed Battle
Here’s the strategic chess move:
Glean’s vulnerability: It’s a standalone product that competes on being the best at one thing (enterprise search). But as Microsoft, Google, and now Zendesk bundle AI search into their existing platforms, Glean has to prove its standalone value is worth the separate purchase.
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.”
This is the 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
The Numbers Tell the Story
Let’s compare:
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.
What Zendesk Has Been Building in AI
This is Zendesk’s 5th AI-focused acquisition in 18 months:
- Klaus (January 2024) – AI-powered QA and coaching
- Ultimate (March 2024) – AI agents for customer service automation
- Local Measure (May 2025) – AI-powered voice/contact center
- HyperArc (July 2025) – GenAI-powered analytics
- Unleash (December 2025) – Enterprise AI search
See the pattern? Zendesk is assembling an AI-native service platform piece by piece. The thesis is clear: 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.
Why Unleash?
Unleash (unleash.so) is a Tel Aviv-based startup. The 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.
The Bigger Picture: Everyone Wants to Own the AI Knowledge Layer
Here’s what’s happening across the industry:
Pure-play enterprise search:
- Glean ($7.2B valuation, standalone)
- Perplexity (launching enterprise search, competing with Glean)
- 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)
The pattern is clear: 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.
What This Means for Founders
If you’re building in enterprise search:
- The market is fragmenting into horizontal (Glean) vs. vertical (everyone else)
- Expect platform vendors to bundle “good enough” search into their products
- Your differentiation needs to be either (a) dramatically better or (b) serving a workflow they don’t touch
If you’re building AI agents for employee service:
- Zendesk just became a much more formidable competitor
- They now have: AI search (Unleash) + AI agents (Ultimate) + QA/coaching (Klaus) + voice (Local Measure) + analytics (HyperArc)
- That’s a full stack. Your wedge needs to be really sharp.
If you’re evaluating enterprise search for your company:
- Don’t just evaluate features—evaluate workflows
- If you’re a Zendesk shop, see what they bundle before buying Glean
- If you need horizontal, company-wide search, Glean is still the leader
- If you need employee service specifically, Zendesk’s integrated approach may be worth more
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 your 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 has to prove the standalone value is worth it. Zendesk has to prove the 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. And with $2B in revenue and an aggressive AI M&A strategy, they’re not messing around.
