Traditionally, we designed services around two constraints:

1. Delivering Value to Customers: Ensuring services deliver on key customer and business outcomes and exceed expectations.
2. Feasibility of Delivery: Balancing resources, finances, and scalability to create a sustainable experience. 

This balance often led to a compromise: high-touch, personalised services for a select few, while the broader customer base received generic, less effective experiences. Resulting in missed opportunities for deeper engagement and ultimately lower retention (particularly among long-tail customers).​

AI changes this narrative.

It builds on key automation that helps you orchestrate customer journey by enabling the delivery of personalised, high-quality content directly to your customer, without needing a CSM to spend hours building bespoke documents.

AI opens the door to making Success Plans available for all customers.

How AI Transforms Success Planning

Without a robust Success Plan to guide them, customers drift through their journey without clear direction, leading to:

• Unfocused implementation
• Limited adoption
• Unclear value realisation
• Lower renewal rates

The traditional constraints of delivering Success Plans—limited resources, finances, and scalability—have meant that most customers missed this vital tool entirely. But with AI, we no longer have to accept these limitations.

AI-powered Success Planning tools connect your success planning process to all available data around the customer’s persona, package, and usage, creating bespoke and unique Success Plans for every customer. Check out how GitLab is doing this.

With AI, Success Planning becomes:

#1 Intelligent

• Draws insights from data on what made similar customers successful
• Recommends optimal milestones based on historical patterns
• Suggests personalised strategies based on customer characteristics

#2 Dynamic

• Updates automatically based on customer behaviour and evolving needs
• Adjusts timelines when it detects deviations from the expected path
• Continuously refines recommendations as more data becomes available
• Provides proactive alerts when customers drift from their success trajectory

#3 Democratic

• Available to all customers, not just premium segments
• Scales without sacrificing personalisation
• Delivers high-touch guidance to the long tail of customers

Success Plans as the Foundation for Continuous Value

When powered by AI, Success Plans become the backbone of your entire customer journey:

• Onboarding That Never Ends (learn more here): Success Plans transition seamlessly from initial onboarding to continuous education. New feature adoption gets incorporated automatically into existing plans. And customer progress is tracked against evolving goals, not just initial setup.
• Continuous Value Communication: Success Plans provide on-demand visibility of progress toward goals. While automated milestone celebrations keep customers engaged and motivated.
• Measurable Outcomes: Clear dashboards highlight feature adoption milestones directly within Success Plans. And gamification elements track progress and encourage continued engagement.

Building Your AI Success Plan Program

Ready to transform your Success Planning with AI? Here's how to begin:

1. Audit your current Success Plans: Identify which elements could be automated or enhanced with AI. 
2. Start with data integration: Connect customer usage data to your Success Planning tool. If you don't have one, check EverAfter.
3. Create adaptive templates: Design Success Plan frameworks that can flex based on customer segments. Find a template in this awesome library.
4. Implement continuous tracking: Move from static documents to dynamic dashboards. The goal is to be able to monitor progress and intervene.
5. Gradually expand access: Start offering AI-powered Success Plans to segments previously without access.

The Future of Success Planning

The pillars of effective Success Planning remain unchanged:

1. Understanding your Customer's Goals
2. Delivering Measurable Outcomes
3. Communicating Success Clearly

Embracing AI in success planning is not just about adopting new technology; it's about reimagining the customer journey to be more personalised, efficient, and impactful. By leveraging AI, businesses can provide tailored experiences that resonate with customers, fostering deeper engagement and long-term loyalty.

Are You Ready to Transform Your Customer Success Strategy with AI?

Daphne Costa Lopes

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RetentionOS Update

If you're ready for more, there are 3 ways I can help you:

• The CSM Skills and Drills Guide: This simple guide has helped over 300 CSMs develop the skills to ace retention and growth targets. You'll find 8 core CSM skills with tools and frameworks to support them and 24 exercises to help you and your team develop these skills.  

• The 2025 CS Trends Report: With over 450 participants across companies of every size, this free report shines a light on what are the top challenges and opportunities for Customer Success for next year.

• Book a 1:1 Consultation: Sometimes content isn't enough. You need to talk through the nuances of the challenges to devise a good strategy. Get 1:1 access to Daphne’s 10+ years of experience building and scaling Customer Success teams starting at €300.