Cassidy vs. Glean

Overview

LLMs created a new era of automation. While previous workflow automation platforms could only automate tasks with basic if/then logic, LLMs unlocked complex reasoning in natural language.  

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However, the quality of LLM outputs and decisions is highly dependent on the specific context they’re given. Insufficient, disorganized, or outdated data can cause AI to respond inconsistently (or even hallucinate), making it hugely unreliable for business automation. Enter: Cassidy. 

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Cassidy is a more intelligent automation platform that makes every decision with full context on your business. 

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How it works: Cassidy’s knowledge base connects to your company’s existing knowledge tools (Slack, Notion, Drive, etc.) and automatically cleans, prepares and keeps your business’s data up-to-date. It removes the concept of “one-size-fits-all” logic and instead allows your team to reliably build powerful AI workflows that make complex, human-level decisions, all with a nuanced understanding of your company. 

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Cassidy was built for both non-technical and technical users, making effective AI automations accessible to teams of all shapes and sizes. Today, we’re thrilled to announce our $3.7 million funding led by The General Partnership, Neo, Comma Capital, Spacecadet Ventures, Ride Ventures, and angels like Erik Goldman (Co-founder of Vanta), Jason Dorfman (CEO of Orum), Zach Sims (CEO of Codecademy). We closed our round in November 2023 and have been growing fast...

What makes Cassidy’s automations ‘intelligent’

Companies typically want to consolidate their tooling, and since Cassidy's workflows are tailored to how a business operates, it works ‘intelligently’ in a few different ways: 

It gets smarter with more interactions

Cassidy’s automations improve over time. Each interaction cites its sources, allowing you to verify and exclude specific information through human-in-the-loop processes. This transparency ensures your data remains accurate and up-to-date. As more interactions occur, Cassidy’s performance is refined, incorporating added context and prompt adjustments to continually enhance the system’s reliability.

It understands your business

Cassidy connects with all knowledge tools (Slack, Sharepoint, Confluence, etc.) to give AI context on your business, customers, competitors, brand voice, and more. It pulls the information in real-time so that it’s constantly up-to-date with what’s happening at your company and in the market. This gives Cassidy human-like judgment, and keeps responses consistent across your entire team.

It’s fully composable software

Cassidy allows teams to quickly build custom AI automations and agents. Companies can tailor the software to how their business operates, designing workflows that match their exact team’s processes. We're creating hundreds of AI action blocks combined with all the leading AI models (all included with your plan) so you can bring your AI tech stack into a unified platform. 

AI that can run asynchronously

Cassidy’s workflows allow you to build automations that run even while you’re sleeping. You can create triggers from hundreds of different tools to automate tasks automatically. Because our AI runs with specific guardrails and the full context of your company, you can trust it to perform reliably without needing a human in the loop.

Built for teams of all shapes and sizes

We're making AI automations accessible to teams of all sizes and skill sets. To stay ahead in the age of AI, automation is no longer optional—everyone needs to be able to build out automations. Cassidy is designed to make it incredibly easy for non-technical teams to use and build complex automations. We offer a library of pre-made workflows and a simple text-to-workflow creation process. For more technical teams and granular use cases, Cassidy has the flexibility to add code and prompt engineering. Cassidy also has enterprise-grade permissioning and security that you can trust to keep your data private and encrypted. You can set advanced user-level permissions for your automations and knowledge data to keep your data secure. Learn more about our security (including compliance with SOC II) at trust.cassidyai.com. 

Cassidy in the real world 

We started Cassidy a little over a year ago and are continuously blown away by our customers’ creativity, from startup founders automating responses to RFPs to global public companies automating their sales enablement flows for 12k+ companies. Some use cases to spotlight: 

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RVezy is a leader in online RV rentals that built a suite of sales enablement and customer success automations. Since their business model and ideal customer persona are incredibly nuanced, they couldn’t rely on typical if/then logic or scoring criteria to prioritize and respond to customers. The team embedded Cassidy into their workflows to automate customer support triaging, handle chargeback disputes, and draft replies with highly nuanced context. These automations understand RVezy’s business inside-out and make high-context judgments for each ticket trained on thousands of previous support inquiries.

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“Cassidy allows us to be much more proactive in addressing critical customer complaints - automatically escalating issues to a manager who can solve customer problems quickly”

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E78 Partners, a leading advisory firm, utilizes Cassidy's AI automations for research and knowledge transfer across teams. They've built automations that are hyper-personalized to support industry research and client facing projects.

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"Cassidy personalizes its AI tools to know our business, clients, and industries better than any other AI-enabled company. Across the board, our team is obsessed with using Cassidy as a copilot to refine solutions, research external industry insights, streamline knowledge transfer across teams and find creative ways to automate the day-to-day monotonous tasks."

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Lexer, a customer data platform, generates responses to RFPs in minutes. Their team created an AI workflow that extracts questions from documents, searches their knowledge base for answers, then writes a thorough response in Lexer’s brand voice.

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“I never thought I’d be able to automate responding to our RFPs until I found Cassidy. It was incredibly easy to connect my tools, and helps us respond 3x faster to customers so we can close more deals.”

What’s next

At Cassidy, we believe AI is going to become more and more embedded into how companies operate, starting with automations. If what we’re building resonates, check out our many open roles at cassidyai.com/careers 👈

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.

1. Learn about AI
2. Use it in your industry
3. Share online how you’re doing that.
4. 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.

Cassidy and Microsoft 365 Copilot both bring AI assistance to the workplace, but they differ significantly in scope and approach. Cassidy is an AI-native automation platform designed to integrate AI into diverse workflows across an entire business, while Microsoft 365 Copilot functions as an assistant within Microsoft’s suite of apps (Word, Excel, Outlook, Teams).

While Copilot is useful for enhancing productivity within Microsoft tools, Cassidy goes further by enabling cross-platform workflows, providing AI model flexibility, and offering enterprise-level support. Below is a comparison of how Cassidy and Microsoft Copilot stack up across key areas:

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AI Flexibility: Multiple Models vs. Single Model

Cassidy offers extensive AI flexibility. It supports multiple AI models, including OpenAI’s GPT-4, Google’s Gemini, and Anthropic’s Claude. This allows organizations to choose the best AI for different tasks and future-proof their automation as better models emerge.

Microsoft Copilot, on the other hand, is locked into Microsoft’s chosen OpenAI model. Users have no control over the AI provider and must rely solely on the models Microsoft decides to deploy. This lack of flexibility can limit performance in specific use cases where another model might be a better fit.

Workflows & Automation: Multi-Step vs. In-App Only

Cassidy enables true end-to-end AI-powered workflows across multiple tools and steps. Its no-code workflow builder lets users create AI-driven automations that take action across apps, process data, and even trigger real-time alerts. For example, Cassidy can read an incoming email, analyze its content, update a CRM, and notify the right person in Slack—all in one seamless process.

Microsoft Copilot, however, is limited to acting within individual Microsoft 365 apps. It assists with tasks like writing emails in Outlook or summarizing documents in Word but does not offer full automation across tools. Microsoft’s Copilot Studio allows for some custom Copilot assistants, but these are largely confined to Microsoft’s ecosystem and require developer setup.

Integration Scope: Diverse Tools vs. Microsoft-Only

Cassidy connects with over 100+ third-party applications, including CRMs, ticketing systems, knowledge bases, and communication platforms like Slack and Teams. It integrates deeply with both Microsoft and non-Microsoft tools, ensuring seamless automation across an organization’s full tech stack.

Microsoft Copilot, by contrast, is designed primarily for Microsoft 365 users. It works well within the Microsoft suite but has limited or no native integration with third-party tools like Slack, Google Drive, or external CRMs. This lack of connectivity makes it difficult to implement AI-driven workflows outside of Microsoft’s ecosystem.

Enterprise Scalability: Organization-Wide vs. Individual Use

Cassidy is built for enterprise-wide deployment, allowing teams to create AI assistants and workflows that span across departments. Its centralized Knowledge Base ensures that AI-powered automations pull from company-wide data, maintaining accuracy and consistency. Admins can manage access, enforce security policies, and customize AI responses for different teams.

Microsoft Copilot is primarily a personal assistant within Microsoft apps, meaning it functions on a per-user basis rather than being centrally managed for an organization. Any attempt to extend its capabilities across teams would require significant developer effort and remain constrained within the Microsoft environment.

Onboarding & Implementation: Hands-On vs. Self-Service

Successfully implementing AI tools in an enterprise requires more than just software—it requires expert guidance, training, and ongoing support to ensure adoption and success. Cassidy provides a white-glove onboarding experience, working directly with each organization to build, customize, and integrate AI solutions effectively.

When you adopt Cassidy, you get:

• A Dedicated Account Manager – Your team is assigned a Cassidy AI expert who helps design AI assistants and workflows tailored to your business needs. This ensures your AI solutions align with your processes and deliver real impact from day one.
• Team Training Sessions – Cassidy provides hands-on training to help teams in sales, marketing, support, and operations seamlessly integrate AI into their workflows. This ensures that AI adoption happens smoothly across departments, not just in isolated pockets.
• Weekly Office Hours – Cassidy hosts live Q&A sessions where customers can get expert advice, troubleshoot challenges, and explore new use cases for AI within their business.
• Private Slack Support – A direct line of communication with Cassidy’s team, allowing customers to ask questions, request features, and receive real-time assistance whenever they need it.

This high-touch support model ensures that organizations don’t just buy AI tools—they successfully implement them and maximize their value.

By contrast, Microsoft Copilot follows a self-service onboarding approach. While Microsoft provides documentation, FAQs, and standard admin guides, there is no dedicated onboarding or personalized implementation support. If an organization needs additional guidance, they may have to work with third-party Microsoft partners at an extra cost. This means that adoption relies heavily on internal IT teams to configure Copilot and train users, which can slow down AI implementation—especially for enterprises looking to scale AI across departments.

Final Thoughts: Why Cassidy Stands Out

Microsoft 365 Copilot is a useful personal productivity tool within the Microsoft suite, helping with writing, summarizing, and task management inside apps like Word and Outlook. However, it lacks true AI-powered workflow automation and is restricted to Microsoft’s ecosystem.

Cassidy, on the other hand, enables end-to-end AI automation across your entire tech stack. It integrates with multiple tools, supports multiple AI models, and allows enterprises to build custom workflows that adapt to their specific needs. With hands-on onboarding, admin controls, and broad AI flexibility, Cassidy is the better choice for businesses looking to deploy AI across departments and tools.

Ready to see how Cassidy can automate your workflows? Book a demo today.