Cassidy vs Microsoft Copilot: AI Automation vs Microsoft 365 Assistant

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.

Overview

When evaluating automation platforms, Cassidy and Loopio often surface as contenders for streamlining RFPs and proposal management. However, these platforms differ significantly in their scope and flexibility. Loopio is a narrowly focused RFP response tool, providing structured, predefined workflows specifically built around proposal generation. In contrast, Cassidy is a powerful, contextual AI automation platform designed to dynamically adapt to your unique enterprise processes, far beyond just RFP responses.

Cassidy not only accelerates RFP responses but automates complex, context-driven workflows across sales, customer support, operations, HR, and beyond. Loopio’s rigid structure may speed up repetitive proposals but lacks adaptability, restricting its usefulness for enterprises with specific needs for the RFP processes.

Feature Comparison

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Contextual AI Automation vs. Static Content Lookup

Cassidy’s AI-powered automation goes far beyond simple content retrieval. Its contextual AI understands and dynamically adapts to your business processes, continuously improving workflows by extracting information, generating context-aware responses, and automating complex tasks end-to-end.

Loopio’s automation is essentially limited to suggesting previously stored answers from its content library. This static approach requires significant manual upkeep and struggles to handle non-standard or complex RFP scenarios, often forcing users back into tedious manual work.

Custom Workflows Tailored to Your Enterprise

No two businesses handle proposals or processes the same way. Cassidy recognizes this and provides highly customizable AI workflows precisely adapted to your company’s specific requirements. You can define your processes, tone, and even AI behavior, creating workflows that perfectly match your operational style.

Loopio, however, restricts teams to predefined structures. Its limited customization options mean that if your proposals vary significantly, your team might frequently revert to manual interventions, reducing the platform's value.

Unified Enterprise Knowledge

Cassidy’s enterprise-wide knowledge base centralizes your critical business content—whether proposal answers, customer interactions, internal policies, or sales materials—in one intelligent repository. This interconnected knowledge powers all of Cassidy’s automation tools, ensuring consistency and continuous improvement.

Loopio’s knowledge management is isolated to RFP-related content, creating data silos and limiting your enterprise’s ability to leverage insights across different departments or workflows.

Interactive AI Assistants Where You Work

Cassidy embeds intelligent, interactive AI assistants directly into Slack, Microsoft Teams, Chrome browsers, and web applications. This enables employees across your enterprise to access real-time, contextual support seamlessly within their daily workflow.

Loopio provides no interactive AI assistance outside its own interface, restricting content lookup and limiting employee engagement and accessibility.

Scalable AI for Enterprise Teams

Cassidy prioritizes scalable enterprise adoption with comprehensive onboarding, dedicated account management, ongoing training, and personalized support. This approach ensures quick implementation, team-wide adoption, and continuous optimization across various business units.

Loopio’s onboarding and scalability are limited strictly to proposal teams, with minimal ongoing support or adaptability to broader organizational needs.

Cassidy: The AI Platform Built for Your Entire Business

Loopio offers efficiency strictly within rigid, predefined proposal workflows. Cassidy, however, delivers expansive, contextual AI automation that adapts to your unique processes, breaks down knowledge silos, and supports dynamic, enterprise-wide workflows. Cassidy represents the smarter long-term investment, equipping your business for success beyond RFPs.

Ready to unlock the full potential of AI-driven automation?

Book a Demo today and experience the Cassidy difference firsthand.

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.