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

The future of sales is not a distant vision; it's unfolding in real-time, driven by AI's capability to refine and personalize every interaction.

At Cassidy, we're at the forefront of this evolution with contextual automation—a method that doesn't just look to the future but actively shapes the present. By leveraging this technology, sales teams today must embrace AI not only to keep pace but to lead in an already transformed market.

Our platform ensures your sales strategy is not just reactive but proactive, turning every sales challenge into an opportunity. Let's delve into how AI is already making a difference, in the sales world, and how tools like Cassidy can help you every step of the way.

Prepare and Research Meeting Invitees Before Sales Calls

Walking into a sales call unprepared is no longer an option. Cassidy’s AI-powered workflows ensure your team is equipped with detailed, actionable insights about meeting invitees before every call. This workflow does the heavy lifting for you by gathering data like company overviews, recent company news, and detailed information about the invitees.

Cassidy’s AI even dives into LinkedIn profiles to provide a comprehensive look at the organization and its stakeholders. All this information is compiled into a shareable document that can be accessed by your entire team, ensuring everyone is aligned and prepared. Plus, it integrates seamlessly with your calendar tools, so you have everything ready to go before the meeting starts.

For example, before a call, Cassidy can provide a summary of the prospect’s recent achievements or challenges, helping your team tailor the conversation and demonstrate value from the first interaction. It’s an all-in-one preparation tool that sets your sales calls up for success.

Deal Tracking Efficiency

Sales teams often struggle with the time-consuming task of sifting through vast amounts of data to find relevant customer information. That's where Cassidy's workflows come in, allowing you to pull up all the details on a customer or a deal in just seconds, thanks to AI.

This feature enables you and your team to instantly search through records, helping to get right to the point, personalize your approach, and keep the sales process moving smoothly. It's like having a super-efficient assistant dedicated to making your life easier.

For example, before calling a client, you can quickly search for their name in the system. Within seconds, you'll have access to their purchase history, recent interactions, and any notes from previous meetings, allowing you to tailor your conversation effectively.

Find Key Decision-Makers to Multithread Sales Deals

Finding the right decision-makers can be the difference between closing a deal and letting it slip away. Cassidy’s simplifies the process by identifying key stakeholders and influencers within a target organization.

Instead of manually researching or guessing who holds decision-making power, Cassidy analyzes CRM data, email communications, and external sources to provide you with a clear map of key players. This enables your team to craft targeted messages that resonate with each stakeholder, streamlining the sales process.

For example, if a deal involves multiple departments, Cassidy highlights which contacts to prioritize and how to address their specific concerns. This insight empowers your team to build stronger connections and accelerate deals without unnecessary delays.

Automatically Enrich New Leads

Finding and understanding new leads can be a daunting task, often requiring extensive research to gather all the necessary details. With Cassidy's AI, this process is automated, allowing you and your team to instantly enrich new leads with relevant information.

By integrating with various data sources, Cassidy's workflows automatically add valuable insights like job titles, company details, and contact information to your CRM. This feature ensures that when you engage with a new lead, you're equipped with a comprehensive profile, enabling more personalized and effective outreach.

For instance, when a new lead enters your system, instead of manually searching for their background, the AI enriches their profile, providing you with the context to tailor your communication, thereby improving conversion rates and enhancing your sales strategy's efficiency.

Streamline Team Responses with Verified Answers

Consistency and accuracy are crucial when responding to client questions, especially during RFP processes. Cassidy’s Answer Hub ensures that your team always delivers approved, verified responses to common queries, saving time and boosting credibility.

This feature centralizes all your organization’s approved answers in one place, making it easy for reps to find and share the right information instantly. No more scrambling to verify details or waiting on approvals—Cassidy’s AI ensures that everyone on your team is aligned.

So if you're ever in a situation where a client requests specific technical details or compliance information, reps can quickly search the Answer Hub to pull up the correct response, ensuring accuracy and consistency in their communication. This not only speeds up the sales process but also builds trust with clients, showing that your team is organized and dependable.

Automatically Transcribe, Save, and Query Meeting Notes

After a sales meeting, capturing and organizing notes can be time-consuming, often leading to missed insights or follow-up opportunities. Cassidy's AI simplifies this by automatically transcribing, saving, and enabling you to query meeting notes.

This feature ensures that all discussions, decisions, and action items from your meetings are recorded without manual effort. You and your team can then easily search through these notes for specific details or follow-ups, enhancing your ability to recall important points and personalize future interactions.

For example, post-meeting, the AI transcribes the conversation, saving it in your system where you can later ask for information like "What was the client's concern about pricing?" or "What follow-up was promised?" This automation not only saves time but also ensures that no detail is lost, making your sales process more organized and responsive.

Create Personalized Cold Emails that Stand Out

Cold emails are only effective when they feel anything but cold. Cassidy’s AI leverages LinkedIn insights, CRM data, and other sources to create hyper-personalized emails that capture attention and increase response rates.

The workflow analyzes key details about your prospect, like their role, company updates, and recent achievements, and crafts tailored outreach messages that feel authentic. For example, instead of sending a generic “just checking in” email, Cassidy generates a message that highlights the recipient’s recent LinkedIn activity or a relevant company milestone, positioning your sales team as informed and relatable.

Even better, Cassidy’s AI ensures these personalized emails are ready to send with minimal effort, saving your team valuable time while maintaining a high-touch approach. With smarter, data-driven outreach, you can turn cold leads into engaged prospects.

Personalize Sales Meeting Follow-Up Emails

The follow-up after a sales meeting can make or break the relationship. Cassidy’s AI ensures every follow-up email feels thoughtful, relevant, and timely, keeping the momentum going with your prospects.

This workflow uses meeting notes, CRM data, and insights from the conversation to draft tailored emails that highlight key discussion points, address objections, and outline next steps. For example, if pricing was a concern during the meeting, Cassidy’s AI suggests a follow-up email that includes a breakdown of value-add features or a link to relevant case studies.

The tool also automates the process, saving your sales team time while maintaining a high level of personalization. With smarter follow-ups, Cassidy helps your team stay top-of-mind and move deals forward faster.

Auto-Completing Security Questionnaires

Navigating through security questionnaires can be a significant hurdle in finalizing sales, often requiring extensive time and expertise to complete accurately. With Cassidy's AI, this process is streamlined, enabling you and your team to auto-complete these questionnaires with ease.

By integrating with your existing security documents, knowledge base, and other resources, Cassidy's workflows automatically fill in the answers, ensuring compliance and accuracy. This feature turns what could be a laborious task into a swift operation, allowing you to focus on closing deals rather than paperwork.

For example, when a new security questionnaire is required, instead of manually searching for responses, the AI quickly pulls the necessary information, completing the form in seconds. This efficiency not only speeds up the sales process but also reduces the risk of errors, making your sales cycle smoother and more secure.

Give Sales Team the Ability to Answer Technical Questions

Handling technical questions doesn’t have to be exclusive to engineers or IT specialists. Cassidy’s AI bridges the gap by enabling non-technical support and sales reps to confidently answer complex technical inquiries.

This feature pulls from your company’s existing knowledge base, integrating seamlessly with tools like Notion, Jira, Confluence, and internal wikis to provide accurate, approved responses in seconds. For example, when a prospect asks a detailed question about product integration or security protocols, Cassidy’s AI suggests the right answer instantly, saving time and preventing delays.

This workflow also ensures responses are aligned with RFP standards and company-approved language, reducing the risk of errors or miscommunication. By equipping your team with these tools, Cassidy enables everyone to contribute to technical discussions without requiring deep expertise, improving responsiveness and fostering trust with prospects.

Use Cassidy to help boost your Sales Performance

Ready to see how Cassidy can transform your sales strategy, streamline workflows, and help your team close deals faster? Start your journey with Cassidy today and experience the future of sales firsthand. Try for free today

‍

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.

‍

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

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.  

‍

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. 

‍

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

‍

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. 

‍

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: 

‍

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.

‍

“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”

‍

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.

‍

"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."

‍

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.

‍

“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 👈