Cassidy and Glean serve different purposes in the enterprise AI space. Cassidy is an AI automation platform that executes multi-step workflows, while Glean is primarily an enterprise search tool designed to help teams find and retrieve information.
The biggest difference? Cassidy doesn’t just find information—it takes action. Whether automating RFP responses, triaging support tickets, or generating approvals, Cassidy applies AI to automate real work, while Glean focuses on retrieving knowledge across enterprise systems.
Here’s a quick feature comparison:
Feature
Cassidy (AI Workflow Automation)
Glean (Enterprise Search)
Core Focus
✅ AI-driven workflow automation
❌ Enterprise search & retrieval
Built-in AI
✅ AI powers every step
⚠️ AI helps find info, but doesn’t act
Knowledge Base
✅ Uses AI to automate tasks with context
✅ Centralized knowledge retrieval
AI Assistants
✅ Real-time assistants in Slack, Teams, Chrome
❌ No interactive AI assistants
Speed of Deployment
✅ Fast, no-code setup for targeted use cases
❌ Requires full org-wide data ingestion
Workflows vs. Agents
✅ No-code workflow automation
⚠️ AI “agents” generate workflows dynamically
Security & Access
✅ Enterprise-ready (SOC 2, permissions, SSO)
✅ Strong security & granular permissions
Ideal Use Case
✅ Automating multi-step business processes
✅ Finding company-wide knowledge
Cassidy: AI That Works For You
Cassidy isn’t just about surfacing information—it’s about automating work. It can:
Draft & process RFPs in seconds, pulling from company knowledge.
Triage and route support tickets automatically, reducing workload.
Enrich and update CRM records, helping sales teams move faster.
Generate personalized emails, reports, and summaries with real business context.
With no-code workflow automation, teams can deploy Cassidy quickly for immediate value—no IT-heavy setup required.
Glean: Search, Not Automation
Glean specializes in enterprise knowledge retrieval, making it easy for employees to find information across wikis, emails, and files. It’s designed to:
Reduce internal support tickets by giving employees self-service answers.
Help new hires get up to speed by centralizing company knowledge.
Improve decision-making by surfacing relevant reports and past work.
Glean’s AI-powered search is fast and accurate, but it doesn’t automate tasks or workflows—users still have to take action manually.
Speed of Deployment: Quick Wins vs. Heavy Rollout
Cassidy: Deploy in days, not weeks, by targeting a single high-impact use case (e.g., automating customer support responses or drafting proposals). AI assistants and workflows can be embedded directly into Slack, Teams, and email without deep integrations.
Glean: Requires indexing the entire organization’s data before it’s useful. Companies must integrate Glean with all tools and set up permissions before employees can start using it.
Cassidy delivers value immediately, while Glean is a long-term IT investment.
Automation Workflows vs. AI Agents
Cassidy: Users build clear, step-by-step workflows—for example, analyzing an incoming request, updating a system, and drafting a response—all automatically. It’s predictable, structured automation that businesses can rely on.
Glean: Introduces AI “Agents”, which attempt to dynamically generate workflows on the fly based on broad user goals. While promising, this approach lacks fine control and predictability, making it less suited for critical business processes.
Enterprise Readiness & Security
Both platforms meet enterprise security standards, including SOC 2 compliance and strong access controls.
Cassidy provides role-based access and data privacy controls, ensuring AI assistants only access relevant information.
Glean enforces strict user permissions, making sure employees only see data they are authorized to access.
While both platforms prioritize security, Cassidy is faster to implement without requiring full company-wide data integration.
Who Should Use Cassidy vs. Glean?
Use Cassidy if you need:
✔️ AI-powered workflow automation that acts, not just retrieves data ✔️ Fast, no-code deployment for targeted automation use cases ✔️ Real-time AI Assistants in Slack, Teams, and Chrome ✔️ Automations that replace manual tasks like RFPs, support triaging, and CRM updates
Use Glean if you need:
✔️ Enterprise-wide search to help employees find existing knowledge ✔️ A centralized knowledge hub that connects to all your company’s data sources ✔️ AI that retrieves information but doesn’t take action
Final Thoughts: Why Cassidy Wins
Glean is a powerful knowledge retrieval tool, but Cassidy goes further—using AI to actually get work done. If your goal is to automate business processes, reduce manual effort, and deploy AI-powered workflows quickly, Cassidy is the clear choice.
This might be the biggest opportunity in AI right now: take your industry expertise, apply new AI knowledge, and become the AI expert in your industry.
See, a recent McKinsey report stated that AI adoption in the workplace has actually remained stagnant from 2021 to 2023.
I believe that’s because most people have a general understanding of AI, but they have no idea how to use it in their specific industry. There’s a huge opportunity to become the person who shows people how to apply AI to your industry. Focus on teaching use cases actually relevant to their daily work.
The more niche you get, the bigger impact you can have.
How do you become the AI expert in your industry?
First, position yourself as the "AI Person" at your company. Share your learnings and experiments with colleagues and other people in your industry.
There's no shortage of people looking to make their lives easier. Start by helping those around you.
To take it a step further, share your insights online.
You know I love TikTok, but it doesn’t matter which platform you choose. TikTok, LinkedIn, Twitter, Instagram, YouTube, whatever. The steps are simple.
Learn about AI
Use it in your industry
Share online how you’re doing that.
Repeat for months-years
If your content is helpful and you do it for long enough, you’ll start to be seen as the AI expert for your industry. You'll have the opportunity to make a significant impact by applying the power of AI to address specific problems within your field.
Remember: every industry needs an AI expert, you can be it.
Picture an AI system that doesn’t just answer questions or move data around, but truly understands what it’s doing.
It knows your brand policies, notices patterns in text, pulls the right documents when needed, and takes meaningful actions — all without you writing a single line of code.
That’s contextual automation, and it’s at the heart of what Cassidy is building.
Let’s explore what contextual automation is, why it’s different from old-school automation, and how Cassidy brings it to life in a way that feels both futuristic and easy to grasp.
What is Contextual Automation?
Traditional automation often relies on simple triggers: “When X happens, do Y.” This works well when you’re dealing with neat, structured data — like updating spreadsheets or sending emails. But modern businesses deal with messy, unstructured information, such as emails, chat logs, PDFs, and policy documents.
These sources don’t follow a tidy format, and they can hide key details in plain text.
Contextual automation takes things further by letting AI read and interpret that unstructured data. Instead of just passing it along, the system understands why it matters. It can cross-reference facts from documents, product specs, or internal policies, then take the right action without requiring you to manually dig through it all.
Advantages of Contextual Automation
Contextual automation improves two things: the speed at which you access information and your ability to act proactively. With accurate, up-to-date insights available in seconds, your team can make better decisions and achieve outcomes faster.
Context-Driven Actions Cassidy goes beyond simply sharing data. It understands the context and takes the right actions, whether that means drafting a response, sending timely updates, or verifying that you’re being compliant.
Empowering Your Team Our workflows are essentially going to act as virtual agents, offering valuable insights and context for your employees. Whether you need background information on a video call participant, detailed company reports, or alerts on competitor activity, there are different ways to help your team get their job done faster and more efficiently.
Built for Everyone You don’t need technical expertise or prior knowledge of AI to set up powerful workflows with Cassidy. Every department can benefit from contextual automation. If you’d like to see some examples, explore the dozens of templates on our use-case page and see how easy it is to get started.
Why Standard Automation Falls Short
Old-school tools shine with structured tasks. If you want to copy data from one cell to another, they work great. But they tend to break down when handling open-ended or ever-changing content.
Most of them weren’t built for large volumes of text, making them blind to the deeper context hidden in emails or documents.
They also struggle to chain multiple AI steps together. Many platforms offer a simple “AI step” to summarize text, but they don’t let you blend knowledge from different sources or apply complex logic.
That’s where contextual automation stands out: it goes beyond a single prompt, bringing real understanding and multi-step reasoning into the mix.
How Cassidy Makes it Happen
Cassidy’s platform is built to handle these complexities from the start. We combine AI models, knowledge indexing, and no-code workflow design to deliver a seamless experience.
Unified Data Model
All of your information — from PDFs to support centers to spreadsheets — can be indexed in Cassidy’s knowledge base. If the AI needs to confirm any kind of policy, it can jump right to the correct section of your policy document. If it’s summarizing a support ticket, it can also review past chats for context.
Multi-Step AI Workflows
Rather than relying on a single rule, Cassidy chains multiple AI actions into a seamless workflow. Let’s say you want a full picture of a new lead and an updated lead score in your CRM as soon as their email lands in your inbox.
Cassidy starts by gathering the basics, like name and email, then enriches the profile with insights from LinkedIn and the company’s online presence. Next, it calculates a lead score with a brief explanation and updates your CRM, all in one smooth, connected flow. Every step builds on the last, ensuring your team receives a complete, context-rich lead profile that’s ready for action.
No-Code Building Blocks
We offer drag-and-drop “building blocks” for tasks like sentiment analysis, text comparison, or drafting replies. You snap these pieces together to form custom workflows that match your needs. This makes it easy for non-technical users to build advanced automations without learning to code.
Flexible and Future-Ready
As AI evolves, Cassidy evolves too. If a new large language model comes out, you can plug it into your existing workflows. That means your automations can keep improving without needing a total rebuild.
Real Possibilities with Contextual Automation
Contextual automation isn’t just for one team or department. It can reshape how entire organizations handle their day-to-day operations. Here are a few examples:
Sentiment and Policy Checks Have the AI scan user comments or support tickets, then compare them to your policies. If certain keywords suggest an urgent issue, it can draft a response or alert the right person — all in real time.
Smarter Knowledge Base Searches Save your employees countless hours by making all your information easy to access. Instead of having to manually search through vast knowledge resources, Cassidy scans your data to quickly pull together the best answers and present them in clear, plain language.
Live Document Review Whether it’s a contract or a compliance form, Cassidy reviews your documents by cross-referencing them with your guidelines or any instructions you may have. It quickly identifies potential issues or discrepancies, reducing human error and speeding up the review process.
Task Routing with Context When a new ticket arrives, the system examines its content, references relevant documents, then sends it to the right department with a suggested plan of action.
Where Contextual Automation Is Headed
AI is moving fast, and contextual automation opens the door to even bigger possibilities. Large language models are gaining the ability to handle longer and more detailed text. They’re also getting better at reasoning, remembering past conversations, and adapting as new data comes in.
Adaptive Learning Workflows will watch how users respond and automatically improve their logic over time.
Multi-Model Strategies Different AI models might be used for different steps — one for drafting content, another for fact-checking. Cassidy is built to let you combine models as you see fit.
Custom AI Agents Imagine having an AI “co-worker” who speaks your brand’s language, knows your product lines, and aligns with your unique processes. Giving you all of the accurate and most up-to-date information possible.
Enhanced Oversight As AI grows more powerful, tools for auditing and tracking decisions will also advance, keeping everything accountable and transparent.
Embracing Contextual Automation with Cassidy
The idea of software that truly understands your operations has been a dream for years. Now, with contextual automation, it’s reality. Instead of juggling countless tools that handle only fragments of your workflow, you can unify everything under one AI-driven system that references all the context it needs.
Cassidy is leading the charge by creating a no-code platform that ties AI reasoning together with real-world tasks. If you’ve ever wondered how to automate those “complicated” processes that involve lots of back-and-forth or too many documents to count, we’re here to help you make it simple.
Join us in shaping the future of AI
Check out we bring contextual automation to life. Whether you’re a small team looking to scale everyday tasks or a large enterprise aiming to handle massive volumes of information, our approach adapts to your needs.
Welcome to the next chapter of AI — where automation does more than just shuffle data. It thinks, it interprets, and it delivers truly contextual results. That’s the promise of contextual automation, and we can’t wait to see how you’ll use it. Sign up for a free demo today.
While both Cassidy and ChatGPT Enterprise utilize AI to enhance productivity, they serve distinctly different purposes. Cassidy is a robust, contextual AI automation platform designed to create custom workflows, integrate deeply into your existing tools, and leverage multiple AI models. ChatGPT Enterprise functions primarily as a standalone conversational chatbot built exclusively around OpenAI’s models, lacking deep workflow automation or extensive integrations.
Cassidy provides enterprises with adaptable AI solutions that scale across business units, ensuring contextually intelligent automation tailored specifically to your workflows.
Feature Comparison
Feature
Cassidy
ChatGPT Enterprise
Automation
✅ Flexible AI workflows
❌ Chat-only interaction
AI Models
✅ Multiple AI models (GPT-4, Claude, Gemini)
❌ Single model (GPT-4)
AI Assistants
✅ Integrated in Slack, Teams, Chrome
❌ No external integrations
Knowledge Base
✅ Unified enterprise-wide knowledge
❌ No central knowledge base
Support & Onboarding
✅ Dedicated enterprise support
❌ Generalized, limited support
Flexible AI Models vs. Single Provider Limitation
Cassidy allows your business to leverage multiple leading AI models, ensuring that you always have access to the best tool for the job. ChatGPT Enterprise restricts users to OpenAI’s proprietary models only, significantly limiting your flexibility and potentially future innovation.
Workflow Automation, Not Just Conversations
Cassidy empowers enterprises with comprehensive workflow automation, seamlessly linking multiple business tools and processes to perform tasks end-to-end without human intervention. ChatGPT Enterprise lacks automation capabilities, serving only as a conversational assistant without any capability for task automation or execution across multiple apps.
Integrated AI Assistants vs. Isolated Chat Experience
Cassidy's custom AI assistants integrate seamlessly into everyday business platforms like Slack, Microsoft Teams, and Chrome, delivering contextual support and real-time actions. In contrast, ChatGPT Enterprise offers a closed interface without built-in external integrations, restricting AI interactions to basic conversational exchanges within its own environment.
Centralized Enterprise Knowledge Management vs. Fragmented Storage
Cassidy provides a unified enterprise-wide knowledge base that continuously updates and enriches the context available to your entire organization, ensuring accuracy and relevance. ChatGPT Enterprise’s knowledge storage is ephemeral, restricted to individual sessions, and lacks permanent enterprise-wide knowledge management.
Dedicated Enterprise Support vs. Generic Onboarding
Cassidy offers personalized, white-glove onboarding, dedicated account management, and comprehensive training, ensuring your enterprise successfully adopts and scales AI across teams and processes. ChatGPT Enterprise provides general self-service onboarding with limited personalized support, potentially hindering widespread adoption.
Cassidy: The Smarter Enterprise AI Solution
ChatGPT Enterprise is suitable for standalone, conversational interactions, but Cassidy offers a far more powerful, scalable, and contextual AI solution designed specifically for enterprises. With its extensive integrations, multi-model flexibility, robust workflow automation, and enterprise-grade knowledge management, Cassidy empowers your business to fully harness the potential of AI across your entire organization.
Discover how Cassidy can elevate your enterprise workflows by booking a demo today.
Automate tasks with custom, data-driven workflows.
Chrome extension
Cassidy at your fingertips with browser extensions.
No model training
Unlike ChatGPT, Cassidy never trains with your data.
Knowledge Base
Centralized intelligence for smarter automation.
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