Cassidy vs. ChatGPT Enterprise: Contextual AI Automation vs. Standalone Chatbot

AI Automation Platform vs RFP-Specific Software

Most RFP tools, like Responsive (formerly RFPIO), follow a rigid structure that helps teams fill out questionnaires and manage proposal content. However, no two RFP processes are the same. Cassidy takes a different approach by allowing teams to build custom AI-powered workflows tailored to their exact needs. This flexibility extends beyond RFPs to sales enablement, customer support, and other business functions.

Instead of locking teams into a fixed system, Cassidy adapts to how your team works and ensures AI-powered automations get smarter over time. With Cassidy, RFP automation is just one piece of a larger AI strategy. Your knowledge base fuels multiple workflows, including drafting sales emails, triaging support tickets, and enriching CRM data. Rather than siloing knowledge across different AI tools, Cassidy keeps everything in one system, making it easier to scale automation across the entire organization.

Here is a breakdown of how Cassidy and Responsive compare and why a flexible AI platform is the smarter investment for enterprises.

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AI That Adapts to Your Workflow, Not the Other Way Around

Every company handles RFPs differently, yet many tools take a one-size-fits-all approach. Responsive is designed around structured proposal workflows that help teams quickly fill in responses using an existing content library. This speeds up the process but follows a predefined structure, requiring teams to work within a set system.

Cassidy takes a more flexible approach. Instead of following a fixed template, Cassidy allows teams to customize every part of the process. AI-generated responses, workflow steps, and automation rules can all be tailored to match the unique way each team operates. Whether automating RFPs, summarizing documents, or handling customer support inquiries, Cassidy adapts to your specific needs.

With Cassidy, AI becomes a true automation engine that evolves with your business. Teams can:
✅ Customize AI outputs to ensure responses match their brand and tone
✅ Choose from multiple AI models like GPT-4 and Claude for different types of tasks
✅ Build workflows that combine AI-powered data extraction, analysis, and response generation

Responsive is built for proposal teams, while Cassidy offers a broader AI-powered automation platform that scales across multiple workflows. For enterprises looking to expand AI beyond RFPs, Cassidy provides a more flexible and future-proof solution.

AI Assistants vs. Lookup-Based AI

One of the biggest differences between Cassidy and Responsive is how teams interact with AI.

Cassidy provides fully customizable AI Assistants that can be trained for any specific task. Whether acting as a content copilot that ensures responses are in your exact brand voice or an AI that automatically replies to emails for your sales team, Cassidy’s Assistants adapt to each team’s needs. They can be embedded in Slack, Microsoft Teams, Chrome, CRMs, and more, allowing employees to ask questions, generate content, or complete tasks instantly. Unlike rigid chatbots, these Assistants understand context, pull from company knowledge, and take action in real time.

Responsive’s AI works more like a smart lookup tool. Instead of a free-form assistant that users can chat with, Responsive’s AI is designed to retrieve RFP content when proposal managers need it. When working on an RFP, the AI searches the content library, suggests relevant answers, and can auto-fill responses. This makes it useful for quickly handling repetitive questions, but it doesn’t function as an AI assistant that can handle broader business tasks.

While Responsive’s AI is embedded in the RFP process, it lacks the flexibility of Cassidy’s Assistants, which can be custom-built for different roles and deployed across multiple workflows. Whether teams need a sales AI to draft outreach emails, a support bot to answer customer FAQs, or a compliance assistant to review policies, Cassidy provides the AI-powered copilots that teams can rely on every day.

Enterprise Knowledge: A Smart System for All AI Tools, Not Just RFPs

AI is only as powerful as the knowledge it can access. Cassidy gives enterprises a single, centralized knowledge base that connects documents, wikis, CRM data, and support tickets to power multiple AI-driven workflows. Instead of siloing data across different AI tools, Cassidy lets teams build and deploy AI assistants for sales, support, operations, and more, all pulling from the same up-to-date system.

Responsive’s knowledge is built only for RFPs. Its Content Library stores past responses and approved Q&A pairs, ensuring accuracy for proposals but limiting its usefulness elsewhere. Other teams can’t easily repurpose this data, forcing companies to rely on separate tools for sales emails, customer support, and internal workflows, creating more silos instead of reducing them.

With Cassidy, knowledge isn’t just stored, it is actively used to automate processes across teams. Enterprises can quickly spin up new AI tools without rebuilding from scratch, making AI smarter, more consistent, and easier to manage at scale.

Choose AI That Grows With Your Business

Cassidy is built for enterprises that want AI-powered automation across multiple teams and workflows, not just RFPs. It provides the flexibility to build custom AI assistants and workflows that scale with your organization, ensuring knowledge stays connected and automation gets smarter over time.

Responsive is a strong choice for companies that need a structured tool specifically for RFPs, proposals, and sales questionnaires. However, if your goal is to consolidate AI efforts, avoid data silos, and automate more than just one function, Cassidy offers a more powerful and future-proof solution.

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.

AI Automation vs. Enterprise Search

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:

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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.

Ready to see Cassidy in action? Book a demo today.

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