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- How to Deliver Proactive Re-Onboarding to Increase Customer Lifetime Value
How to Deliver Proactive Re-Onboarding to Increase Customer Lifetime Value
Identify triggers to set re-onboarding in motion to re-engage customers
🧪 Customer Onboarding News
The community got involved on LinkedIn to answer the question “What's your go-to icebreaker question on first calls with new customers?” I enjoyed the funny ones! 👉 Take a look here.
I want to shout out Jaya Choudhary for her suggestion: “What’s the one thing, you wish, everyone understood about your business from day one?”
Want to see your customer onboarding news, jobs, webinars, and more here?
Click on the video below for a few of my thoughts on today’s topic. ↓
Some might think that customer onboarding is a one-way journey.
But in B2B SaaS there is a wealth of opportunity to solidify a customer’s success with your product.
It starts with world-class customer onboarding experiences. It’s bolstered by proactive re-onboarding strategies throughout the lifecycle.
Don’t think of re-onboarding as a dirty word! It’s not an admission that the original onboarding experience failed.
It’s a strategic plan to zoom in on flags that could lead to potential churn at the end of a contract if left to compound.
Let’s look at how to go about creating one, shall we? ↓

🧪 The Project: The Re-Onboarding Strategy
This is a process for further down the lifecycle when the initial onboarding has already been successfully completed.
Step 1: Create your triggers
Establish clear signals that indicate a customer might need re-onboarding.
Look for:
Overall product usage dipping below a baseline
Key champion or user leaves the company
Feature adoption rates decline
High number of support tickets showing knowledge gaps
Negative feedback or lacklustre feelings in quarterly business reviews
Frequent cancelling of strategic calls throughout lifecycle
You can start by being aware of these triggers and noticing them manually. Then you can progress to a system of scoring where a certain number will trigger the re-onboarding plan.
Once you are happy with the process, you can add it into the health score too.
Step 2: Design the assessment
Create a way to evaluate customer needs. You can schedule a strategic review call with the customer.
Give the impression (and follow through) that it’s a value-add consultation.
Have your data to hand. Highlight their successes to date and how it aligns with their original success goals.
Ask them if these goals are still relevant or if they need to be updated. Once you have that feedback, move on to some comparisons.
Examples:
Current vs. historical usage patterns - is there an obvious dip? Find out why.
Team composition and training status - is it still the same team? Are there any new team members or promotions that have changed how the product is being used?
Feature utilisation gap analysis - are they maximising the product to get the most out of their contract? Are they missing out on valuable features that could save them time or money?
This is an exercise in digging deep with the customer to get to root causes. Remember when I talked about the 5 Whys? Read up on the technique below ↓
Step 3: Build your packages
Not every customer needs the full treatment. Aim to create some modular packages that can be customised to their needs.
Create tiers that work for your product. Here is a basic example:
Refresh - Quick feature updates, best practices, success metrics reset.
Rebuild - New team training, workflow optimisation, new milestone settings.
Relaunch - Complete re-onboarding for major team changes, documentation creation, realignment with executive sponsors, longer period with more check ins.
Price these packages accordingly.
Step 4: Frame the conversation
Position re-onboarding as a value add that will have big benefits.
Here are some examples of how you can approach the conversation once the re-onboarding plan has been triggered.
"We've noticed some changes in your organisation, and we'd love to invest in your team's success. Can we talk about getting them up to speed?"
"Our refresh program has helped similar customers achieve a 40% increase in ROI. I think it’s worthwhile discussing if you would like to see those results too."
"We've developed some new best practices that align perfectly with your growth objectives. I’d love to share that with you, does that sound of interest?"
"I was looking at your account, and I’ve identified some opportunities to streamline your workflows. Would you like to know how?"
Step 5: Measure and learn
Track the impact of your re-onboarding efforts over the following few months. The length of this depends on how complex your product is and whether the re-onboarding was lengthy.
Some things to assess:
Measure customer usage patterns - have they improved?
Document customer feedback & satisfaction scores - are they more engaged? Is the feedback positive? Are the scores improving?
Monitor support tickets - are you seeing a reduction?
Monitor customer health scores - are they improving?
🔍 Renewal & expansion - ultimately, we are aiming for greater customer lifetime value, expert users, and advocates. Measure the impact of proactively implementing re-onboarding plans on Net Revenue Retention and ARR as well.
This helps to elevate the role of customer onboarding in your company.
🤓 The Analysis
Re-onboarding isn't about fixing problems. It's about proactively maintaining the success you've already built.
The concept of periodic re-engagement allows you to transform what could be seen as a failure point into an opportunity for better customer partnerships.
What you can expect after implementing this project:
Reduced churn risk
Increased feature adoption
Stronger customer relationships built
Higher customer lifetime value