Announcing Cassidy’s $3.7M Fundraising

Sales isn’t just about charm and persistence anymore—it’s about being equipped with the right tools to work smarter, not harder.

Today’s sales teams face mounting pressures: tight deadlines, information overload, and the constant need to stay one step ahead of the competition. If that sounds familiar, you’re not alone.

Enter sales enablement.

It’s more than flashy tools or a stack of PDFs; it’s about creating a framework that empowers reps at every stage of the sales process. From crafting data-driven strategies to closing deals faster, effective enablement ensures teams have what they need to thrive.

But what if your tools could do more than support your strategy? What if they could actively optimize it?

That’s where artificial intelligence changes the game.

By integrating AI-driven solutions like Cassidy, sales teams can operate leaner, streamline processes, and focus on what matters most: closing deals.

Whether it’s automating research, scoring leads, or drafting personalized outreach, Cassidy ensures every part of the enablement journey is faster, smarter, and more cost-effective. Here's how AI can help you at every part of a sales journey.

Identifying and Qualifying Leads

Every sales journey begins with finding the right prospects, but not all leads are created equal. Wasting time chasing low-value leads can drag down even the most experienced sales teams. This is where precision in lead qualification becomes essential — and where Cassidy’s AI-driven lead scoring takes the spotlight.

Quick Refresher: Why Lead Qualification Matters
For enterprise sales teams, efficient lead qualification is the difference between spinning wheels and driving revenue. By zeroing in on prospects with the highest likelihood of conversion, your team can:

• Focus on what matters: Spend less time chasing dead ends and more time building relationships with high-value prospects.
• Shorten the sales cycle: Well-qualified leads tend to move through the pipeline faster.
• Boost conversion rates: Targeted efforts lead to better outcomes, improving your bottom line.

How Cassidy’s AI Supports Lead Qualification

Cassidy leverages advanced AI to analyze vast amounts of data—historical deals, engagement trends, and company profiles—to provide a dynamic lead score.

We integrate seamlessly with your CRM, delivering real-time updates that keep your team ahead of the game.

With Cassidy’s agents doing the heavy lifting, salespeople are empowered to focus on what they do best: building relationships and closing deals.

Here’s how Cassidy enhances lead qualification:

• Dynamic Lead Scoring: Evaluate prospects in real-time using historical data and engagement patterns.
• Seamless CRM Integration: Syncs directly with your CRM to keep data fresh and actionable.
• Automated Research: Gathers and analyzes prospect information, eliminating manual tasks.
• Customizable Scoring Models: Tailor lead evaluation criteria to fit your unique sales process.
• Real-Time Updates: Provides instant feedback as new data comes in, ensuring your team stays agile.

Using Cassidy means your team spends less time qualifying leads and more time closing them.

This shift not only streamlines operations but also enhances your team’s ability to hit targets consistently. When every second counts, Cassidy ensures your sales process is as efficient and impactful as possible.

Streamlining Research and Prep

Sales isn’t just about having the right prospects—it’s about understanding them. But research can be one of the most time-consuming parts of the process, often pulling reps away from selling. Between digging through company profiles, market trends, and competitor insights, valuable hours slip away.

Quick Refresher: Why Efficient Research Matters
For enterprise sales teams, thorough research is the foundation of a successful pitch. Without it, even the best strategies can falter. Here’s why research efficiency is a game-changer:

• Better conversations: Tailored insights lead to more engaging, impactful discussions.
• Stronger positioning: Knowing your prospect’s challenges and market landscape helps you stand out.
• Time savings: Automating routine research frees up time for strategic selling.

How Cassidy’s Research Agent Optimizes Prep

Cassidy’s Research Agent automates the grunt work, delivering key insights directly to your team. It scours market reports, company news, and internal data, then consolidates everything into a digestible format.

Whether it’s preparing for a meeting or understanding a prospect’s business, Cassidy ensures your reps walk in fully armed with the right information.

Here’s how Cassidy enhances research and preparation:

• Automated Competitor Insights: Stay ahead by knowing how your prospects stack up against their competition.
• Customized Prospect Summaries: Get tailored snapshots of each lead, highlighting the most relevant data points.
• Instant Market Trend Reports: Keep a pulse on industry shifts without lifting a finger.
• Real-Time Updates: Ensure your team always has the latest insights before making contact.

By letting Cassidy handle the heavy research, your team can focus on delivering value where it matters most—engaging prospects and driving deals forward. When research takes minutes instead of hours, you’re setting your team up for success.

Personalizing Outreach

In the crowded world of enterprise sales, generic pitches simply don’t cut it. To truly connect with prospects and move deals forward, every interaction needs to feel tailored and relevant. But crafting personalized messages at scale is no small feat—unless you’ve got the right tools in place.

Quick Refresher: Why Personalization Matters
Personalized outreach isn’t just a nice-to-have; it’s essential for driving engagement and building trust. Here’s why it’s critical:

• Increased Engagement: Personalized emails and messages are far more likely to get opened and responded to.
• Stronger Relationships: Tailored communications show prospects that you understand their specific needs and challenges.
• Higher Conversion Rates: Prospects are more likely to take the next step when they feel the pitch is designed just for them.

How Cassidy Scales Personalization

Cassidy leverages AI to make personalization effortless. By analyzing key data points—like industry, company size, and recent interactions—Cassidy generates custom messaging that resonates with each prospect. No more copy-pasting templates or spending hours tweaking emails.

Here’s how Cassidy transforms your outreach strategy:

• Tailored Email Templates: Generate personalized emails at the click of a button, saving time without sacrificing quality.
• Industry-Specific Recommendations: Provide insights and solutions that speak directly to a prospect’s industry pain points.
• Behavior-Based Follow-Ups: Automatically adjust messaging based on how prospects engage with your content.
• Consistent Tone and Branding: Ensure every message aligns with your company’s voice, creating a seamless experience.

With Cassidy, your team can deliver personalized outreach at scale, building stronger connections and moving deals through the pipeline faster. Time spent on crafting the perfect message becomes time spent closing the next deal.

Accelerating the Sales Cycle

In enterprise sales, time is everything. The longer a deal lingers in the pipeline, the greater the risk of losing it to a competitor or internal delays. To stay ahead, sales teams need to move quickly, keeping momentum high and bottlenecks low.

Quick Refresher: Why Speed Matters
A fast-moving sales cycle isn’t just about efficiency—it’s about maximizing opportunities and reducing risks. Here’s why speed is essential:

• Reduce Churn Risk: The faster a deal progresses, the less chance prospects have to second-guess or disengage.
• Increase Deal Volume: Shorter cycles mean your team can close more deals in the same timeframe.
• Maintain Prospect Momentum: A seamless, fast process keeps prospects engaged and excited about your solution.

How Cassidy Speeds Things Up

Cassidy removes the common roadblocks that slow down sales cycles. By automating time-consuming tasks like RFPs, contract generation, and compliance document prep, Cassidy helps your team keep deals moving without sacrificing accuracy or quality.

Here’s how Cassidy accelerates the sales cycle:

• Automated Proposal Generation: Create polished, customized proposals in minutes.
• Streamlined Contract Reviews: Generate contracts with pre-approved clauses to avoid legal bottlenecks.
• Pre-Filled Compliance Documents: Reduce back-and-forth with automated, error-free forms.
• Real-Time Task Management: Ensure every step of the process is completed on time with automated reminders and updates.

With Cassidy powering your sales cycle, deals close faster, and your team stays focused on what’s next. When speed meets precision, you gain a competitive edge that keeps your pipeline flowing.

Closing Deals Faster

Everything in sales ultimately leads to one goal: closing the deal. It’s the final hurdle, and how efficiently your team navigates this stage can make or break your revenue targets. But closing isn’t just about getting signatures—it’s about ensuring every step is smooth, timely, and impactful.

Quick Refresher: Why Closing Efficiency Matters
The closing phase is where all the hard work pays off. Here’s why optimizing this stage is critical:

• Revenue Impact: Faster closes mean quicker revenue realization.
• Resource Optimization: Efficient closings free up reps to focus on new opportunities.
• Customer Satisfaction: A seamless closing process builds trust and sets the stage for long-term relationships.

How Cassidy Helps You Close Deals

Cassidy takes the friction out of closing deals by automating key steps and providing instant access to critical deal information. From streamlining document workflows to enabling real-time collaboration, Cassidy ensures nothing stands in the way of sealing the deal.

Here’s how Cassidy empowers your team during the closing phase:

• Instant Document Prep: Generate contracts, invoices, and closing summaries in seconds.
• Automated Approval Workflows: Get necessary sign-offs without delays.
• Centralized Deal Insights: Provide reps with a complete view of deal history and key touchpoints.

With Cassidy, your team can close deals with confidence, speed, and precision. By eliminating last-minute bottlenecks and ensuring a smooth transition from proposal to contract, Cassidy helps you turn opportunities into wins—faster.

Post-Sale Follow-Up

Closing the deal is only the beginning. In enterprise sales, the post-sale follow-up is critical for nurturing client relationships, identifying upselling opportunities, and ensuring long-term satisfaction. A well-executed follow-up strategy turns one-time buyers into loyal customers and maximizes the value of every deal.

Quick Refresher: Why Post-Sale Follow-Up Matters
The real revenue potential often lies beyond the initial sale. Here’s why post-sale engagement is essential:

• Strengthen Client Relationships: Regular follow-ups show your commitment to their success, building trust and loyalty.
• Uncover Upsell and Cross-Sell Opportunities: Happy clients are more likely to invest in additional products or services.
• Boost Retention Rates: Continued engagement ensures your clients stay with you long-term.

How Cassidy Supports Post-Sale Success

‍Cassidy streamlines the follow-up process, helping your team stay connected with clients without adding extra workload.

By automating routine tasks and providing actionable insights, Cassidy ensures every interaction adds value.

Here’s how Cassidy enhances post-sale engagement:

• Automated Follow-Up Reminders: Never miss a chance to check in or provide additional value.
• Upsell and Cross-Sell Recommendations: Identify opportunities for expanding the relationship based on past behaviors and needs.

With Cassidy, your team can maintain meaningful client relationships that drive long-term success. By staying proactive and informed, you’ll not only secure repeat business but also position your company as an indispensable partner.

Start Using AI to Help With Sales Enablement

From prospecting to closing and beyond, Cassidy empowers your sales team at every stage of the journey. By streamlining workflows, automating time-consuming tasks, and delivering actionable insights, Cassidy ensures your team can focus on what they do best—driving revenue and building lasting client relationships.

Ready to transform your sales process? Start a free trial today! 

In this article, we'll explore the key aspects that differentiate Cassidy from ChatGPT Enterprise, focusing on Cassidy's models, core features, security, support, and more to understand its advantages for implementing AI into your organization.

AI Models and Flexibility

Cassidy supports multiple AI models, including OpenAI's GPT-4o & GPT-4, Google Gemini, and Anthropic Claude. This approach offers a broader range of capabilities and a higher level of reliability depending on the use-case. For instance, we’ve found that Claude is the best for content writing, while GPT-4o is the best for internal Q&A. Unlike ChatGPT, which relies on OpenAI's models alone, Cassidy provides a more versatile AI experience.

The important part about being model agnostic is that when newer and better models are released, they will get added to Cassidy automatically. There’s no fear of purchasing and investing in an AI model that will quickly become outdated.

Knowledge Base

ChatGPT Enterprise, similar to other Large Language Models (LLMs), faces the inherent challenge of potentially generating misinformation or 'hallucinations'. A key limitation in this context is the model's inability to provide source citations for its generated content.

More specifically, ChatGPT Enterprise doesn’t support the ability to directly integrate with and store files in a centralized Knowledge Base. As of the latest update, you can add Google Drive and Microsoft Sharepoint files via the “chat” feature, but there’s no way to integrate or store them (and have it live sync when changes are made in your Google Drive, SharePoint, etc.). This makes Cassidy more ideal for use cases that require robust internal knowledge management and searching across thousands of files- unlike ChatGPT which is only ideal for one-off uploading of files.

Cassidy's Knowledge Base securely connects with over 100 tools and updates in real-time, prioritizing privacy. This comprehensive knowledge management system empowers Cassidy's AI capabilities with a rich context for generating accurate and relevant responses. Whenever it generates a source, it cites its sources so you can assure the accuracy of all your information.

AI Assistants

Cassidy's AI Assistants, powered by the Knowledge Base, perform specific tasks such as drafting replies to customer emails and assisting internal HR operations while maintaining contextual consistency across teams.

While ChatGPT Enterprise has GPTs that function similarly to Assistants, there are a few key reasons that Cassidy’s Assistants perform better:

1. The ability to add context via your Knowledge Base allows for much higher accuracy compared to solely having detailed roles.
2. The ability to easily share Assistants across your entire team for consistency (e.g. customer responses, RFP builders, blog post creation, etc.).
3. Beyond Chat, you can take your assistants into multi-step workflows for greater creativity (more on this in the next section).

Multi-step Workflows

While ChatGPT focuses strictly on chats, Cassidy allows you to build and run multi-step workflows without the need for back and forth chatting. This feature is ideal for automating specific processes that you run in a similar way every time - it’s more effective to set it up once and just have to run it versus always having to chat back and forth.

With workflows, we can integrate with tools that ChatGPT for Enterprise can’t. For example, via Workflows, you can integrate with Zendesk and automate customer support. You can plug into Slack and easily deploy Slackbots to answer employee questions. We integrate with Zapier so you can plug into 6,000+ other apps and use Cassidy as the “AI Glue” to scrape the internet, craft customized content, and search your Knowledge Base - all with actual context on your business.

Our workflows allow you to bulk run as well - this is great for automating processes that require multiple iterative runs rather than a single run. Good examples: Responding to an RFP that has questions in hundreds of rows, uploading a sales lead list, and automatically generating dozens of custom cold emails, etc.

Integrations

Cassidy integrates with key business tools like Google Drive, SharePoint, Notion, Slack, Zapier, and much more. There is also a Webhook for incoming data and an API (both GET and POST) which allow you to securely integrate data from practically anywhere. This connectivity allows for seamless integration of AI Assistants. With Cassidy, you get access to thousands of integrations to trigger actions (e.g., drafting emails, sending Slack messages, responding to tickets, creating contacts, publishing blog posts) that are not possible with ChatGPT Enterprise.

Security and Data Privacy

Cassidy prioritizes data security with enterprise-grade protocols, ensuring user data safety. Both are SOC2 compliant and follow the industries top practices for security and privacy.

Support and Onboarding Process

Unlike ChatGPT for Enterprise, Cassidy believes in onboarding all of its Enterprise teams and providing ongoing support. From setting up your integrations to setting up complex workflows with your team, our goal is to continue unlocking new use-cases that make your team more productive.

More specifically, with your workspace, your team gets access to:

1. Your own Dedicated Account Manager to help your team build AI assistants and workflows customized to your use cases.
2. Team training sessions to train specific functional teams (sales, marketing, customer support, etc.) on how to best use Cassidy.
3. Weekly Office Hours to help get questions answered live on calls.
4. Slack channel with the Cassidy team to answer questions quickly or create requests for new integrations.

Because we can provide so much support & onboarding, Cassidy actually enables your team to effectively roll out AI, rather than just being another software tool in the mix.

Reach out to learn more

If you’re interested in learning more about our Enterprise offering, reach out to our sales team at team@cassidyai.com.

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.

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