Onboarding isn’t a one-time event—it’s an ongoing journey.

 

A few weeks ago I shared ideas on how to scale onboarding, and I mentioned that most onboarding processes fail because they become disconnected from product growth.

 

This thought struck a chord. I got dozens of messages from you, asking to expand.

 

We're so used to seeing onboarding as "the first 90 days" that most of us miss the opportunity to drive the adoption of new tools as they are released. 

 

As companies release new tools, expand their product offerings (and adjust pricing to reflect added value), customers often continue using only their initial use cases.

 

This creates an imbalance in the ROI equation.

 

Customers are paying more but not realising additional value, leading to dissatisfaction and, ultimately, churn.

 

But here’s the good news—if you treat onboarding as a continuous process rather than a single moment, you can drive sustained engagement, deeper adoption, and long-term retention.

 

Why Onboarding Is Never Truly Over

 

Traditional onboarding focuses on getting customers to initial activation. But that’s just the beginning.

 

Customers need ongoing education to:

• Adopt new features: As your product grows, so do its capabilities. Customers need guidance to unlock their full potential.
• Adjust to changing needs: Businesses evolve, and customers’ goals shift. Onboarding must keep pace.
• Prevent stagnation: If customers only use a fraction of your product, they’ll eventually look elsewhere.
• Build long-term loyalty: Consistently reinforcing value keeps customers engaged and invested in your solution.

Static onboarding fails because it assumes customers reach a final destination.

 

In reality, successful onboarding is a continuous loop of learning, adoption, and value realisation. You need to design a set of programs that match your business objectives and your customer's needs, and ensure there are many opportunities to adopt new tools through the customer journey. 

 

How to Keep Customers Engaged with Continuous Onboarding

 

To sustain long-term engagement, you need to develop an ongoing approach to onboarding. Here's how you develop one:

 

#1 Segment Customers by Lifecycle Stage

 

Customers require different guidance at different points in their journey. Instead of a one-size-fits-all approach:

• Identify onboarding needs for new users, power users, and at-risk customers.

• Provide tailored learning paths based on engagement levels and product usage.

• Use in-app prompts to deliver relevant guidance at the right moment.

For more on personalising onboarding to evolving customer needs, check out this article: No More One-Size-Fits-All Onboarding in 2025.

 

#2 Introduce Features Based on Jobs to be Done

 

Instead of bombarding users with everything upfront:

• Implement features that introduce new tools in the context of their use case.

• Highlight benefits specific to each user’s workflow.

• Create micro-learning modules to help customers master advanced functionality over time.

Understanding your customer's Jobs to be Done can be a really helpful framework to build these modules.

 

#3 Create Continuous Engagement Strategies

 

Automated touchpoints ensure customers stay engaged after initial onboarding:

• Send emails or in-app messages when customers underutilize key features.

• Trigger educational content when users explore new areas of the product.

• Use milestone-based nudges to encourage deeper product usage.

You can start the journey by using your CRM to help tailor communication. But this gets really complex really quickly when you start layering jobs to be done, personas, and lifecycle stages.

 

Onboarding automation tools can help scale your efforts whole providing an awesome customer experience through a dedicated interface.

 

If you want to learn how these interfaces can improve engagement and enhance the customer experience, this case study from Frontify is a great read.

 

#3 Measure Progress and Celebrate Wins

 

Continuous onboarding requires visibility into progress:

• Provide dashboards that highlight feature adoption milestones.

• Use gamification elements, such as badges or progress bars, to motivate users to continue to learn (you'd be surprised how well this works!).

• Send success stories to inspire further engagement.

The reality is that continuous onboarding requires a system that allows your customer to match their company goals and their learning needs. A dynamic Success Plan is possibly the best way to ensure this happens.

 

Fresh out of the press is this free masterclass that Everafter is hosting soon how to build a Success Plan Programme (you bet I'll be there!)

 

#4 Leverage Customer Feedback for Evolution

 

Onboarding should evolve alongside customer needs:

• Analyse how customers are engaging with the learning content.

• Analyse product usage trends to refine educational content.

• Conduct ongoing surveys to identify knowledge gaps.

• Adjust onboarding flows based on where users struggle most.

And don't forget to set the right expectations with your customer. They will #alwaysbelearning when it comes to how to get the most value from your product.

 

Want to learn more about how to continuously optimise onboarding for lasting customer success?  Watch this great on-demand webinar: Practical Strategies to Empower Your Digital Onboarding Programs. 

 

Why Continuous Onboarding Works

 

When onboarding is treated as an ongoing process, customers:

• Stay engaged longer because they continuously discover value.

• Adopt features more effectively, leading to deeper product usage.

• Develop brand loyalty by seeing your product evolve alongside their needs.

Onboarding isn’t a box to check—it’s the foundation of a thriving, engaged customer base. Make it an ongoing priority, and you’ll never stop driving value.

 

Are you ready to rethink onboarding as an evolving journey?

Daphne Costa Lopes

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RetentionOS is launching soon! 

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.