Cassidy vs. Loopio

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! 

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.  

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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. 

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

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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. 

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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: 

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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.

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“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”

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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.

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"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."

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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.

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“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 👈

Overview

While both Cassidy and ChatGPT Enterprise utilize AI to enhance productivity, they serve distinctly different purposes. Cassidy is a robust, contextual AI automation platform designed to create custom workflows, integrate deeply into your existing tools, and leverage multiple AI models. ChatGPT Enterprise functions primarily as a standalone conversational chatbot built exclusively around OpenAI’s models, lacking deep workflow automation or extensive integrations.

Cassidy provides enterprises with adaptable AI solutions that scale across business units, ensuring contextually intelligent automation tailored specifically to your workflows.

Feature Comparison

Flexible AI Models vs. Single Provider Limitation

Cassidy allows your business to leverage multiple leading AI models, ensuring that you always have access to the best tool for the job. ChatGPT Enterprise restricts users to OpenAI’s proprietary models only, significantly limiting your flexibility and potentially future innovation.

Workflow Automation, Not Just Conversations

Cassidy empowers enterprises with comprehensive workflow automation, seamlessly linking multiple business tools and processes to perform tasks end-to-end without human intervention. ChatGPT Enterprise lacks automation capabilities, serving only as a conversational assistant without any capability for task automation or execution across multiple apps.

Integrated AI Assistants vs. Isolated Chat Experience

Cassidy's custom AI assistants integrate seamlessly into everyday business platforms like Slack, Microsoft Teams, and Chrome, delivering contextual support and real-time actions. In contrast, ChatGPT Enterprise offers a closed interface without built-in external integrations, restricting AI interactions to basic conversational exchanges within its own environment.

Centralized Enterprise Knowledge Management vs. Fragmented Storage

Cassidy provides a unified enterprise-wide knowledge base that continuously updates and enriches the context available to your entire organization, ensuring accuracy and relevance. ChatGPT Enterprise’s knowledge storage is ephemeral, restricted to individual sessions, and lacks permanent enterprise-wide knowledge management.

Dedicated Enterprise Support vs. Generic Onboarding

Cassidy offers personalized, white-glove onboarding, dedicated account management, and comprehensive training, ensuring your enterprise successfully adopts and scales AI across teams and processes. ChatGPT Enterprise provides general self-service onboarding with limited personalized support, potentially hindering widespread adoption.

Cassidy: The Smarter Enterprise AI Solution

ChatGPT Enterprise is suitable for standalone, conversational interactions, but Cassidy offers a far more powerful, scalable, and contextual AI solution designed specifically for enterprises. With its extensive integrations, multi-model flexibility, robust workflow automation, and enterprise-grade knowledge management, Cassidy empowers your business to fully harness the potential of AI across your entire organization.

Discover how Cassidy can elevate your enterprise workflows by booking a demo today.