In our OG guide on implementing the scaled CX methodology, we learned how to use the best of product-led and sales-led motions to unlock new paths to scale. 

Then, we went deep on nudges - a concrete example of how product and revenue teams can align.

In this latest installment on scaled CX, we’re ripping into another real-world example of how we can create personalized experiences at scale: cohort-based learning.

One of the hardest challenges as a founder is ensuring that customers actually use your shit and see value quickly. But customers don’t just figure out your product on their own. They need structured, targeted learning to guide them through each stage of the journey. We’re building space-age business software, not Spotify for dogs, so some hand-holding will be in order.

Enter cohort-based learning — a strategy that breaks down your users into segments based on their role, behavior, and industry, delivering tailored content that speaks directly to their needs. This approach creates personalized learning paths that improve feature adoption, customer retention, and long-term engagement.

This guide will show you how to implement a cohort-based learning program from the ground up. You’ll set up an in-house content creation team, build learning paths for different personas, and automate the delivery process to ensure your users get the content they need when they need it. And keep using your shit.

Step 1: Set Up an In-House Content Shop

Before you can start building learning paths for your user segments, you need a content creation workflow. This is the engine behind your entire cohort-based learning strategy. 

Assemble Your Content Team

To build a content machine that churns out high-quality material consistently, you’ll need a dedicated team. Working in-house will shorten feedback loops and help you hook your customer learning discipline directly into your other revenue and product teams, unlocking critical internal knowledge for your users.

Here’s who you need to get started:

1. Content Strategist: Responsible for creating the overall learning strategy, mapping out content needs for each persona, and ensuring alignment with business goals.
2. Copywriter: A writer who can turn complex concepts into easy-to-understand copy — everything from case studies and whitepapers to video scripts.
3. Production Specialist: An expert in creating engaging videos, infographics, and interactive tools.
4. LMS (Learning Management System) Administrator: This person manages the technical platforms that deliver your content, ensuring the right users see the right materials at the right time.
5. Subject Matter Experts (SMEs): Experts who provide the deep knowledge necessary to create specific content for each role. These could be internal experts or external participants like interview subjects.

Critical hint: all of these roles can be one person to start, including pulling SME information from internal docs. Keep your content team skeletal as long as possible.

Key Types of Content for Cohort-Based Learning

Your content should be varied and match the needs of each segment. A few key types of content you’ll definitely need:

1. Case Studies:some text
   • Purpose: Showcase real-world examples of how your product delivered value to a customer.
   • Why It’s Important: Builds trust and credibility, especially for executives who need to see results before committing.
   • Format: Written reports, short videos, or slide decks.
2. ROI Calculators:some text
   • Purpose: Help executives calculate the potential return on investment.
   • Why It’s Important: Numbers speak louder than words when it comes to convincing stakeholders.
   • Format: Interactive web-based tools or Google drive templates.
3. How-To Videos:some text
   • Purpose: Teach end users how to perform specific tasks within your product.
   • Why It’s Important: Step-by-step guidance reduces friction and accelerates adoption.
   • Format: 2-5 minute video tutorials.
4. Technical Documentation:some text
   • Purpose: Provide detailed, technical instructions for Admins/IT.
   • Why It’s Important: Builds confidence that your product integrates smoothly and securely into their systems.
   • Format: Knowledge base articles.
5. Strategic Webinars:some text
   • Purpose: Provide high-level discussions on how your product fits into larger business or industry trends.
   • Why It’s Important: Helps executives connect your product to their long-term goals.
   • Format: Live or pre-recorded sessions with Q&A.
6. Interactive Quizzes:some text
   • Purpose: Test user knowledge and reinforce learning.
   • Why It’s Important: Encourages engagement and highlights gaps in knowledge.
   • Format: Online quizzes embedded in your learning platform.
7. In-App Tutorials:some text
   • Purpose: Provide real-time guidance within the platform.
   • Why It’s Important: Reduces onboarding friction and drives faster adoption.
   • Format: Pop-up prompts or interactive walkthroughs built into the app using tools like UserGuiding.

Another critical hint: your product’s interface should (hopefully) be elegant enough that users can get started via obvious cues and empty states. Use tools like in-app tutorials with purpose to highlight new or complex features and extend value. Initial user value should be more obvious than a mushroom cloud. 

Step 2: Segment Your Users

Before you create learning objectives or content, you need to understand who your users are. Segmentation allows you to divide your audience into cohorts based on shared characteristics. By doing this, you can ensure that each group gets the most relevant content.

Role-Based Segmentation

1. Executives: Care about strategy, ROI, and business outcomes.
2. End Users: Focus on how your product improves their day-to-day tasks.
3. Admins/IT: Want to ensure technical compatibility, integration, and security.

Behavior-Based Segmentation

1. Power Users: Have already mastered the basics and are ready for advanced features.
2. Low Engagement Users: Need re-engagement and a clearer understanding of core features.
3. New Users: Require onboarding content to accelerate time to value.

 Industry-Based Segmentation

Your users’ industry often dictates the specific challenges they face. For instance:

• Healthcare: Focus on compliance and data security.
• Retail: Highlight features that drive customer engagement and manage inventory.

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Step 3: Define Learning Objectives for Each Segment

Once your user segments are clear, you need to define learning objectives for each cohort. The learning objectives ensure that the content you create for each group drives measurable outcomes, whether that’s increased feature adoption or improved retention.

Align Learning Objectives with Business Outcomes

1. Executives: Focus on ROI and strategic growth. Executives need to see how your product drives measurable value and impacts long-term business goals.
2. End Users: Aim for workflow mastery. End users should feel confident using the product’s features to improve their daily tasks.
3. Admins/IT: Emphasize technical integration. These users need to understand how your product fits into their existing tech stack without causing disruptions.

Each cohort should have specific, measurable objectives that tie directly to both their needs and your overall business goals.

Step 4: Build Tailored Learning Paths for Each Persona

Each persona’s learning path should deliver content in a sequence that builds confidence and expertise, taking users from basic understanding to full product mastery.

Learning Path for Executives

Why the Sequence Matters: Executives are busy and need to see results before they dive into the technical details. Your learning path should focus on proving ROI and aligning with their strategic vision.

• Step 1: Case Study: Start with real-world examples to establish trust and credibility.
• Step 2: ROI Calculator: Personalize the value by showing how your product will directly benefit their bottom line.
• Step 3: Strategic Webinar: Show how your product fits into their long-term goals and industry trends.

Impact: This sequence quickly demonstrates value, turning executives into champions who can justify the investment to their teams.

Learning Path for End Users

Why the Sequence Matters: End users need practical, actionable guidance. They care about efficiency and mastering the platform so they can do their job better.

• Step 1: In-App Tutorial: Start with an interactive onboarding experience within your product.
• Step 2: How-To Videos: Dive deeper into specific tasks, such as setting up workflows or using key features.
• Step 3: Interactive Quizzes: Reinforce learning and ensure they’ve mastered core functionalities.

Impact: This sequence reduces friction, enabling end users to adopt your product quickly and confidently.

Learning Path for Admins/IT

Why the Sequence Matters: Admins and IT teams care about stability, integration, and security. Your content should focus on technical details and reassurance that your product won’t disrupt their existing systems.

• Step 1: Technical Documentation: Provide detailed, step-by-step instructions for setup and integration.
• Step 2: Advanced Configuration Guide: Show them how to customize the platform for their organization’s specific needs.
• Step 3: Security and Compliance Webinar: Reassure them that your product meets regulatory and security standards.

Impact: This sequence builds trust, ensuring IT teams feel confident in deploying and managing your product.

Step 5: Automate Content Delivery

The success of cohort-based learning hinges on how well you automate the sequencing and timing of educational content, ensuring that it meets users where they are in their journey without overwhelming or under-serving them.

Establishing Effective Sequencing for Automated Content Delivery

The first step in creating a scalable and impactful cohort-based learning program is designing learning sequences. Sequencing refers to the order in which you deliver content to users as they progress through different stages of their journey—whether they’re executives, end users, or IT admins.

Key Principles for Sequencing:

1. Start Simple, Build Up: Users need to feel an immediate win from engaging with your product. Start with the basics, giving them content that provides immediate value, then progress to more advanced material as they build confidence.some text
   • For Executives: Begin with high-level strategic overviews and case studies. After that, move into more detailed ROI calculators and webinars as they deepen their engagement.
   • For End Users: Start with in-app tutorials and basic videos, gradually introducing more complex features and workflows as they gain mastery.
2. Behavioral Triggers: Each stage of the content journey should be triggered by user behavior. If a user has completed a set task, hit a milestone, or logged a certain amount of hours in your platform, it signals they’re ready for more advanced content.some text
   • Example: After a user completes a tutorial on onboarding, they automatically receive an email with advanced feature guides or are prompted in-app with additional tips for power users.
3. Adaptive Learning Paths: Not every user will progress at the same pace. Adaptive learning allows you to adjust content based on how well users engage. If users lag behind, you can send refresher content or additional tutorials; if they progress quickly, they can skip introductory material and dive into advanced features.
4. Microlearning: Microlearning focuses on delivering short, digestible pieces of content rather than overwhelming users with long-form content. This sequencing method is ideal for end users who need to pick up tasks quickly.some text
   • Example: Rather than a 30-minute onboarding webinar, provide 3-minute in-app tutorials spread over their first week.

Timing: How to Make Sure Content Hits at the Right Moment

The next step after sequencing is timing. If content is delivered too early, users might not be ready to act on it; if it’s delivered too late, the learning opportunity has passed, and the user’s experience with the product may have already been negatively impacted. Properly timed content keeps users engaged and helps them succeed.

Key Timing Strategies:

1. Immediate Onboarding: The moment a user signs up, they need immediate hand-holding. For end users, this means automated in-app tutorials that guide them through the essential features of your product.some text
   • Timing: Within the first 10 minutes of logging into the platform, users should receive a walk-through of their key tasks.
2. Time-Based Milestones: After key timeframes (e.g., 7 days, 30 days, 60 days), users should receive content designed to ensure continued engagement.some text
   • Example: On day 7, send a check-in email or trigger in-app notifications that remind users about key features they haven’t yet used. For executives, this could include a follow-up webinar on product ROI; for end users, it could be a deep dive into advanced tools.
3. Usage-Based Timing: If a user logs in for the first time but fails to use key features after a set amount of time (say 14 days), send an email or pop-up prompt reminding them of those features. This prevents users from becoming inactive due to unfamiliarity with the product.some text
   • Example: If an end user has yet to set up a dashboard within the first two weeks, the system should automatically send an instructional video or offer a live onboarding session.
4. Cohort-Specific Timing: Different cohorts will have different cadences for learning. Executives may engage with content less frequently but expect high-impact materials that are easily digestible when they do. End users will need more frequent, task-based updates.some text
   • Timing for Executives: Weekly or bi-weekly check-ins with strategic webinars or one-pagers.
   • Timing for End Users: Daily or every-other-day micro-learning content in the first two weeks, slowing to weekly as their confidence grows.

Tools to Power Your Automated Content Delivery

This could be an entire guide on its own and we always encourage you to review the latest tools that are out there – as we all know, there’s incredible stuff dropping daily when it comes to managing the customer journey. 

Here are some leading example platforms that ensure personalized, timely, and behavior-driven content delivery:

1. Intercom – Contextual In-App Messagingsome text
   • What it Does: Intercom provides highly customizable in-app messaging and email automation, helping users learn through personalized prompts based on their interactions.
   • Unique Nuance: Its strength lies in triggering relevant content based on real-time behavior, ensuring users get immediate help when needed.
   • Why It’s Cool: Intercom's ability to deliver personalized content within the product ensures that users are never lost or disengaged, enhancing learning through real-time feedback loops.
2. Pendo – Behavioral Data for Granular Targetingsome text
   • What it Does: Pendo provides detailed product usage analytics and in-app guides, allowing you to create customized learning paths based on exact user behavior.
   • Unique Nuance: Pendo’s ability to monitor feature usage in real time enables you to serve up highly targeted content that addresses underutilized areas.
   • Why It’s Cool: By combining analytics and in-app messages, Pendo helps you deliver content precisely when a user needs it, improving feature adoption.
3. UserGuiding – Advanced In-App Tutorialssome text
   • What it Does: UserGuiding allows you to build personalized, in-app tutorials and tooltips that guide users through complex workflows.
   • Unique Nuance: UserGuiding enables A/B testing of in-app experiences, allowing you to find the most effective guides for different user cohorts.
   • Why It’s Cool: UserGuding helps you push educational content directly within the product, reducing friction and keeping users engaged in real time.
4. Totango – Customer Journey Orchestrationsome text
   • What it Does: Totango specializes in orchestrating customer journeys based on real-time usage data. It segments users into cohorts and delivers content based on their lifecycle stage.
   • Unique Nuance: Totango’s "SuccessBLOCs" let you create highly targeted learning experiences that evolve as the user’s engagement with the product deepens.
   • Why It’s Cool: Totango combines analytics and content delivery to predict and prevent churn by pushing relevant educational content to at-risk users.
5. Gainsight – Customer Success Platform with Learning Focussome text
   • What it Does: Gainsight tracks user engagement and sends personalized, behavior-driven content based on customer health metrics.
   • Unique Nuance: Gainsight’s strength lies in its ability to assess customer health and deliver content that proactively addresses gaps in knowledge or engagement.
   • Why It’s Cool: Gainsight’s ability to predict churn based on usage patterns and automatically deliver targeted educational content helps prevent user drop-off and boosts retention.

Step 6: Measure, Analyze, and Iterate

No learning program is complete without measurement. You need to track whether your cohort-based learning strategy is driving the desired results.

Key Metrics to Track

• Completion Rates: Are users finishing their assigned learning paths? Why not? 
• Feature Stickiness: Are users accessing key features more frequently  after completing training?
• Customer Satisfaction (CSAT): How satisfied are users with their learning experience?
• Job Success: Most important of all, are users solving problems and completing their jobs-to-be-done in your product more frequently after training? 

Iterate Based on Data

Use your metrics to refine your learning paths. For example, if you notice executives dropping off after the ROI calculator, consider adding additional content to keep them engaged or swapping out a different learning tool. 

TL;DR

Cohort-based learning isn’t just about educating your customers—it’s about increasing adoption, retention, and long-term loyalty. By setting up an in-house content creation machine, segmenting your users, and creating tailored learning paths, you can ensure every customer gets the information they need to crush their challenges.

At Praction, we specialize in helping B2B businesses implement these strategies through our automated Chief Revenue Officer platform and consulting services. Our tailored solutions are designed to increase revenue, refine GTM operations, and enhance customer value, accelerating your path to an exit, acquisition, or IPO.

Ready to scale? We’d love to meet you.  

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