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Contextual Automation: The Next Chapter of AI

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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.

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Announcing Cassidy’s $3.7M Fundraising
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Announcing Cassidy’s $3.7M Fundraising

About us

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 👈

Cassidy vs. Microsoft Copilot
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Cassidy vs. Microsoft Copilot

Industry news

This article will explore the critical differences between Cassidy and Microsoft Copilot. We will focus on Cassidy's diverse features, robust Knowledge Base, and seamless integrations to understand its advantages for organizations looking for efficient AI workspaces.

AI Models and Flexibility

Cassidy supports multiple AI models, including OpenAI's GPT-4o & GPT-4, Google Gemini, and Anthropic Claude. Microsoft Copilot, on the other hand, relies solely on OpenAI. Given Microsoft's partnership with OpenAI, their models are limited to the OpenAI ecosystem. By being model agnostic, Cassidy allows for newer and better models to be added automatically, mitigating the risks of investing in outdated AI models. You also have the added flexibility that certain models are better than others at certain tasks, so you can selectively choose the best models based on your tasks.

Knowledge Base

While you can integrate your SharePoint files within Microsoft 365, you cannot connect other third-party tools like Google Drive. Cassidy's Knowledge Base securely connects with over 100 tools, ensuring real-time updates and privacy. This provides a more comprehensive knowledge management solution to generate accurate and relevant responses across thousands of files, for your entire time.

AI Assistants

Cassidy's AI Assistants, powered by the Knowledge Base, perform specific tasks while maintaining contextual consistency across teams. Microsoft Copilot offers Copilot GPTs that function similarly to Cassidy Assistants; however, they:

  1. Cannot access the same level of context via the Knowledge Base.
  2. Are limited to the Microsoft ecosystem and cannot be used in workflows with non-Microsoft tools.
  3. Are restricted to developer-centric solutions, while Cassidy is a no-code solution accessible to both technical and non-technical users.

Multi-step Workflows

Microsoft Copilot Studio offers limited workflow automation with a focus on deploying Copilot GPT-type assistants to different tools. Unlike Cassidy, which enables users to build and run multi-step workflows for end-to-end automation, Copilot Studio is more technical and less accessible to non-developer users. Their automations, similar to their Assistants (Copilot GPTs), are Sharepoint-centric. Cassidy’s no-code workflows enable comprehensive automations from enriching inbound leads to triggering internal slack messages to your team.

Integrations

Cassidy integrates with key tools like Google Drive, SharePoint, Notion, Slack, Zapier, and many more, allowing for seamless integration of AI Assistants. In contrast, Microsoft Copilot is limited to Microsoft applications like SharePoint and does not integrate with Zapier. Cassidy’s extensive integrations enable you to trigger actions that are not possible with Microsoft Copilot.

Security and Data Privacy

Both Cassidy and Microsoft Copilot prioritize data security with enterprise-grade protocols and follow the industry's top practices for security and privacy. Both platforms are SOC2 compliant. Learn more about Cassidy’s security at trust.cassidyai.com.

Support and Onboarding Process

While Cassidy ensures onboarding assistance for all enterprise teams, Microsoft Copilot offers self-help resources, admin self-help, support plans, partner assistance, and sales contacts. Cassidy's support includes a dedicated account manager, team training sessions, weekly office hours, and a Slack channel to help teams build AI assistants and workflows tailored to their specific use cases. This level of support allows Cassidy users to effectively roll out AI solutions within their organization.

Reach out to learn more

If you're interested in learning more, contact our sales team at team@cassidyai.com.

 10 Ways Your Sales Team NEEDS to Be Using AI Right Now
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10 Ways Your Sales Team NEEDS to Be Using AI Right Now

AI models

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

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Access to the top models

Cassidy includes the top 5+ leading AI models.

Assistants

Intelligent assistants personalized to your team.

Workflows

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.