Cassidy vs. Glean

There are two primary categories for integrating AI into your business:

1. Boosting Internal Productivity - In other words, figuring out how to make your employees and workflows more efficient, so you can deliver better results faster.
2. Enhancing the Customer Experience - Exploring what you can offer on top of your existing products and services to make your customers even happier.

Focusing on internal productivity will help cut costs, while improving the customer experience will help you earn more.

Internal Productivity

In my view, it’s easier to start with internal productivity. Greater AI adoption within your team or even by yourself will lead to a substantial increase in overall productivity. The right AI strategy will turn everyone in your organization into a top performer.

Of course, figuring out the best AI strategy can be tricky. But, I think it’s important to not overthink it. Just starting to use AI tools and sharing them with your team can pave the way for in-depth AI integration across your organization. It’s crucial for everyone to have that “Aha” moment with AI.

At CassidyAI, we’re all about this mission. While we’re still slowly rolling out early access, we’ve been documenting our process publicly because we believe everyone can benefit from the thinking we’re putting into how to build features that truly speed up internal workflows.

We showcased our plugin feature that allows you to bring an AI assistant, custom-trained for your business, virtually anywhere on the internet. It’s been a game-changer for sales, customer success, and marketing teams.

(Check out the demo here. You can also signup for the Cassidy waitlist here)

The point is this: When integrating AI into your business, consider the workflows and tasks that currently exist and explore how AI could be introduced to enhance them. Never assume AI can't help--even small steps towards incorporating AI eventually become meaningful time savings.

Customer Experience

On the other hand, you can drive significant customer retention and growth by thoughtfully using AI in your products and services. This approach requires creativity, as it is not as simple as purchasing an off-the-shelf solution for internal workflow optimization.

AI-enabled features in your products and services could include personalized recommendations, an AI chatbot, or simple AI features that make it easier for people to use your product. The catch is that these features must be unique to your business.

For instance, Shopify customers struggled to optimize their stores properly, so their AI sidekick was developed to do it automatically. Another example: I recently spoke with a personal trainer who introduced an AI chatbot for fitness-related questions because clients struggled with guidance on days they weren’t seeing the trainer.

When considering AI implementation, think about the biggest pain points for your current customers. Why do people churn? Is something stopping them from using your product or service more often? What are their unmet needs?

It’s within these questions, you’ll find opportunities to enhance the customer experience using AI.

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! 

Cassidy and Microsoft 365 Copilot both bring AI assistance to the workplace, but they differ significantly in scope and approach. Cassidy is an AI-native automation platform designed to integrate AI into diverse workflows across an entire business, while Microsoft 365 Copilot functions as an assistant within Microsoft’s suite of apps (Word, Excel, Outlook, Teams).

While Copilot is useful for enhancing productivity within Microsoft tools, Cassidy goes further by enabling cross-platform workflows, providing AI model flexibility, and offering enterprise-level support. Below is a comparison of how Cassidy and Microsoft Copilot stack up across key areas:

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AI Flexibility: Multiple Models vs. Single Model

Cassidy offers extensive AI flexibility. It supports multiple AI models, including OpenAI’s GPT-4, Google’s Gemini, and Anthropic’s Claude. This allows organizations to choose the best AI for different tasks and future-proof their automation as better models emerge.

Microsoft Copilot, on the other hand, is locked into Microsoft’s chosen OpenAI model. Users have no control over the AI provider and must rely solely on the models Microsoft decides to deploy. This lack of flexibility can limit performance in specific use cases where another model might be a better fit.

Workflows & Automation: Multi-Step vs. In-App Only

Cassidy enables true end-to-end AI-powered workflows across multiple tools and steps. Its no-code workflow builder lets users create AI-driven automations that take action across apps, process data, and even trigger real-time alerts. For example, Cassidy can read an incoming email, analyze its content, update a CRM, and notify the right person in Slack—all in one seamless process.

Microsoft Copilot, however, is limited to acting within individual Microsoft 365 apps. It assists with tasks like writing emails in Outlook or summarizing documents in Word but does not offer full automation across tools. Microsoft’s Copilot Studio allows for some custom Copilot assistants, but these are largely confined to Microsoft’s ecosystem and require developer setup.

Integration Scope: Diverse Tools vs. Microsoft-Only

Cassidy connects with over 100+ third-party applications, including CRMs, ticketing systems, knowledge bases, and communication platforms like Slack and Teams. It integrates deeply with both Microsoft and non-Microsoft tools, ensuring seamless automation across an organization’s full tech stack.

Microsoft Copilot, by contrast, is designed primarily for Microsoft 365 users. It works well within the Microsoft suite but has limited or no native integration with third-party tools like Slack, Google Drive, or external CRMs. This lack of connectivity makes it difficult to implement AI-driven workflows outside of Microsoft’s ecosystem.

Enterprise Scalability: Organization-Wide vs. Individual Use

Cassidy is built for enterprise-wide deployment, allowing teams to create AI assistants and workflows that span across departments. Its centralized Knowledge Base ensures that AI-powered automations pull from company-wide data, maintaining accuracy and consistency. Admins can manage access, enforce security policies, and customize AI responses for different teams.

Microsoft Copilot is primarily a personal assistant within Microsoft apps, meaning it functions on a per-user basis rather than being centrally managed for an organization. Any attempt to extend its capabilities across teams would require significant developer effort and remain constrained within the Microsoft environment.

Onboarding & Implementation: Hands-On vs. Self-Service

Successfully implementing AI tools in an enterprise requires more than just software—it requires expert guidance, training, and ongoing support to ensure adoption and success. Cassidy provides a white-glove onboarding experience, working directly with each organization to build, customize, and integrate AI solutions effectively.

When you adopt Cassidy, you get:

• A Dedicated Account Manager – Your team is assigned a Cassidy AI expert who helps design AI assistants and workflows tailored to your business needs. This ensures your AI solutions align with your processes and deliver real impact from day one.
• Team Training Sessions – Cassidy provides hands-on training to help teams in sales, marketing, support, and operations seamlessly integrate AI into their workflows. This ensures that AI adoption happens smoothly across departments, not just in isolated pockets.
• Weekly Office Hours – Cassidy hosts live Q&A sessions where customers can get expert advice, troubleshoot challenges, and explore new use cases for AI within their business.
• Private Slack Support – A direct line of communication with Cassidy’s team, allowing customers to ask questions, request features, and receive real-time assistance whenever they need it.

This high-touch support model ensures that organizations don’t just buy AI tools—they successfully implement them and maximize their value.

By contrast, Microsoft Copilot follows a self-service onboarding approach. While Microsoft provides documentation, FAQs, and standard admin guides, there is no dedicated onboarding or personalized implementation support. If an organization needs additional guidance, they may have to work with third-party Microsoft partners at an extra cost. This means that adoption relies heavily on internal IT teams to configure Copilot and train users, which can slow down AI implementation—especially for enterprises looking to scale AI across departments.

Final Thoughts: Why Cassidy Stands Out

Microsoft 365 Copilot is a useful personal productivity tool within the Microsoft suite, helping with writing, summarizing, and task management inside apps like Word and Outlook. However, it lacks true AI-powered workflow automation and is restricted to Microsoft’s ecosystem.

Cassidy, on the other hand, enables end-to-end AI automation across your entire tech stack. It integrates with multiple tools, supports multiple AI models, and allows enterprises to build custom workflows that adapt to their specific needs. With hands-on onboarding, admin controls, and broad AI flexibility, Cassidy is the better choice for businesses looking to deploy AI across departments and tools.

Ready to see how Cassidy can automate your workflows? Book a demo today.