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Win More Deals With AI-Assisted Sales Enablement

Index

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! 

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

AI models

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

Feature Cassidy ChatGPT Enterprise
Automation ✅ Flexible AI workflows ❌ Chat-only interaction
AI Models ✅ Multiple AI models (GPT-4, Claude, Gemini) ❌ Single model (GPT-4)
AI Assistants ✅ Integrated in Slack, Teams, Chrome ❌ No external integrations
Knowledge Base ✅ Unified enterprise-wide knowledge ❌ No central knowledge base
Support & Onboarding ✅ Dedicated enterprise support ❌ Generalized, limited support

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.

Cassidy vs. Make.com
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Cassidy vs. Make.com

About us

AI-Embedded Automation vs. API-Driven Workflows

Automation has evolved beyond simple “if this, then that” workflows. Cassidy is an AI-native automation platform built for teams that need automation with human-like judgment, not just predefined app connectors. By embedding AI at every level, Cassidy can understand context, make decisions, and even interact with users as an assistant.

Make.com, on the other hand, is a traditional visual workflow builder that treats AI as an external add-on. Users can connect AI services via API modules, but AI isn’t an intrinsic part of every workflow. While Make.com excels at connecting apps in complex scenarios, it lacks built-in AI capabilities like memory or autonomous decision-making.

For enterprise decision-makers, this difference is critical. Below, we compare Cassidy and Make.com across key areas.

Feature Cassidy (AI-Driven) Make.com (Workflow Automation)
AI Integration ✅ Built-in AI powers every step ❌ No native AI, requires external API calls
AI Assistants ✅ Interactive assistants in Slack, Teams, etc. ❌ No AI assistants, only workflows
Enterprise Scalability ✅ Enterprise-grade (SOC 2 Type II, SSO, granular permissions) ⚠️ Basic/limited enterprise features (no SOC 2 yet, simple team roles)
Customization & Flexibility ✅ AI-powered workflows adapt with context ⚠️ Visual workflows with manual logic, no AI context memory
Use Case Fit ✅ Advanced AI use cases (assistant-driven processes, content generation) ❌ Basic app automation, lacks AI-driven actions

Embedded Intelligence vs. "Add-On" AI

Cassidy has AI built into every workflow, making it seamless to analyze data, generate content, and take intelligent actions. Workflows can process unstructured information, reference a knowledge base, and make decisions without needing manual API calls. AI is deeply embedded, meaning users don’t have to configure prompts or external services for each step.

Make.com treats AI as an optional add-on. To use AI, you must manually insert an API call (e.g., OpenAI) into a workflow, manage API keys, and configure prompts. There’s no native memory or knowledge retention, so workflows don’t improve over time. AI in Make is an external tool, not a core part of automation.

AI Assistants – Interactive AI vs. Static Workflows

Cassidy offers real-time AI assistants that integrate into Slack, Teams, and Chrome. These assistants can answer questions, generate responses, and automate tasks based on context. A sales assistant can draft personalized outreach, while an IT assistant can troubleshoot employee requests—all within chat.

Make.com does not have AI assistants. It is focused on background workflows and lacks an interface for employees to interact with AI in real-time. While you could trigger workflows from Slack, Make provides no built-in AI agent that understands context or remembers past interactions.

Enterprise Scalability – Built for Large Organizations

Cassidy is enterprise-ready with SOC 2 Type II compliance, SSO, granular permissions, and access controls. AI can be restricted by role, ensuring security across departments. Its infrastructure is designed for scalability and compliance at an enterprise level. Visit our trust center here.

Make.com, while growing in enterprise features, lacks SOC 2 Type II certification and has simpler role-based permissions. It is well-suited for team-based automation but requires additional governance setup for large-scale deployments.

AI-Driven Flexibility vs. Predefined Workflows

Cassidy lets teams build AI-powered workflows that adapt dynamically. AI can process data, make decisions, and adjust workflows on the fly. Enterprises can use different AI models (GPT-4, Claude) and fine-tune outputs, creating intelligent automations that improve over time.

Make.com is a powerful visual workflow builder but lacks AI adaptability. Workflows require predefined logic, meaning users must manually configure every step. AI cannot influence decisions without external scripting, making automation more rigid.

Use Cases – Where Cassidy Delivers More Value

Cassidy enables AI-powered automation that goes beyond simple workflows, making it ideal for:

  • RFP Automation: AI reads documents, finds relevant answers, and drafts responses using past knowledge.
  • Sales & Marketing Copilots: Assistants research prospects, summarize insights, and generate personalized outreach.
  • Customer Support AI: AI triages support tickets, drafts responses, and escalates urgent issues in real time.
  • HR & Compliance Automation: AI reviews policies, answers employee questions, and ensures regulatory compliance.

Make.com is best for structured app integrations, such as syncing CRM records, sending notifications, or processing simple data flows. AI is an enhancement, not a core function.

Choosing the Right Automation Platform for Your Enterprise

Cassidy is designed for enterprises that need AI-powered workflows and assistants that evolve with their business. Its AI is deeply embedded, making automation more intelligent, adaptable, and scalable.

Make.com is an excellent tool for building structured workflows, but its AI capabilities are limited to external API calls. For enterprises looking to automate complex, AI-driven processes, Cassidy is the more future-proof investment.

Ready to experience Cassidy firsthand? Book a demo today to see how an AI-first automation platform can unify knowledge, streamline processes, and transform the way your teams work.

Cassidy vs. Glean
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Cassidy vs. Glean

About us

AI Automation vs. Enterprise Search

Cassidy and Glean serve different purposes in the enterprise AI space. Cassidy is an AI automation platform that executes multi-step workflows, while Glean is primarily an enterprise search tool designed to help teams find and retrieve information.

The biggest difference? Cassidy doesn’t just find information—it takes action. Whether automating RFP responses, triaging support tickets, or generating approvals, Cassidy applies AI to automate real work, while Glean focuses on retrieving knowledge across enterprise systems.

Here’s a quick feature comparison:

Feature Cassidy (AI Workflow Automation) Glean (Enterprise Search)
Core Focus ✅ AI-driven workflow automation ❌ Enterprise search & retrieval
Built-in AI ✅ AI powers every step ⚠️ AI helps find info, but doesn’t act
Knowledge Base ✅ Uses AI to automate tasks with context ✅ Centralized knowledge retrieval
AI Assistants ✅ Real-time assistants in Slack, Teams, Chrome ❌ No interactive AI assistants
Speed of Deployment ✅ Fast, no-code setup for targeted use cases ❌ Requires full org-wide data ingestion
Workflows vs. Agents ✅ No-code workflow automation ⚠️ AI “agents” generate workflows dynamically
Security & Access ✅ Enterprise-ready (SOC 2, permissions, SSO) ✅ Strong security & granular permissions
Ideal Use Case ✅ Automating multi-step business processes ✅ Finding company-wide knowledge

Cassidy: AI That Works For You

Cassidy isn’t just about surfacing information—it’s about automating work. It can:

  • Draft & process RFPs in seconds, pulling from company knowledge.
  • Triage and route support tickets automatically, reducing workload.
  • Enrich and update CRM records, helping sales teams move faster.
  • Generate personalized emails, reports, and summaries with real business context.

With no-code workflow automation, teams can deploy Cassidy quickly for immediate value—no IT-heavy setup required.

Glean: Search, Not Automation

Glean specializes in enterprise knowledge retrieval, making it easy for employees to find information across wikis, emails, and files. It’s designed to:

  • Reduce internal support tickets by giving employees self-service answers.
  • Help new hires get up to speed by centralizing company knowledge.
  • Improve decision-making by surfacing relevant reports and past work.

Glean’s AI-powered search is fast and accurate, but it doesn’t automate tasks or workflows—users still have to take action manually.

Speed of Deployment: Quick Wins vs. Heavy Rollout

  • Cassidy: Deploy in days, not weeks, by targeting a single high-impact use case (e.g., automating customer support responses or drafting proposals). AI assistants and workflows can be embedded directly into Slack, Teams, and email without deep integrations.
  • Glean: Requires indexing the entire organization’s data before it’s useful. Companies must integrate Glean with all tools and set up permissions before employees can start using it.

Cassidy delivers value immediately, while Glean is a long-term IT investment.

Automation Workflows vs. AI Agents

  • Cassidy: Users build clear, step-by-step workflows—for example, analyzing an incoming request, updating a system, and drafting a response—all automatically. It’s predictable, structured automation that businesses can rely on.
  • Glean: Introduces AI “Agents”, which attempt to dynamically generate workflows on the fly based on broad user goals. While promising, this approach lacks fine control and predictability, making it less suited for critical business processes.

Enterprise Readiness & Security

Both platforms meet enterprise security standards, including SOC 2 compliance and strong access controls.

  • Cassidy provides role-based access and data privacy controls, ensuring AI assistants only access relevant information.
  • Glean enforces strict user permissions, making sure employees only see data they are authorized to access.

While both platforms prioritize security, Cassidy is faster to implement without requiring full company-wide data integration.

Who Should Use Cassidy vs. Glean?

Use Cassidy if you need:

✔️ AI-powered workflow automation that acts, not just retrieves data
✔️ Fast, no-code deployment for targeted automation use cases
✔️ Real-time AI Assistants in Slack, Teams, and Chrome
✔️ Automations that replace manual tasks like RFPs, support triaging, and CRM updates

Use Glean if you need:

✔️ Enterprise-wide search to help employees find existing knowledge
✔️ A centralized knowledge hub that connects to all your company’s data sources
✔️ AI that retrieves information but doesn’t take action

Final Thoughts: Why Cassidy Wins

Glean is a powerful knowledge retrieval tool, but Cassidy goes further—using AI to actually get work done. If your goal is to automate business processes, reduce manual effort, and deploy AI-powered workflows quickly, Cassidy is the clear choice.

Ready to see Cassidy in action? Book a demo today.

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