CHECKLIST
Customer Expansion Readiness Checklist
If your expansion efforts are falling flat, you’re not alone. Most companies are pitching too soon, talking to the wrong people, or failing to show enough value from what’s already been sold. This checklist will help you uncover the friction points hiding inside your customer relationships — and where you might need to realign.
Is Your Customer Expansion Strategy Actually Working?
A diagnostic tool from Thirdside to help you uncover what’s standing in the way of growing your existing accounts.
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If you’re seeing this… |
It might mean… |
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Expansion revenue is flat, or even declining |
Customers don’t see incremental value — or don’t know what’s available |
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“No one wants to talk about upsell” |
You haven’t delivered enough post-sale value to earn that conversation |
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You’re pitching add-ons to end users |
You’re talking to the wrong stakeholder for expansion decisions |
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Your team is getting ghosted |
Customers associate your outreach with sales pressure, not support |
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Accounts are churning before renewal |
The core value proposition was never achieved, let alone exceeded |
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CS is overwhelmed with requests |
Your onboarding or training processes are broken, delaying value attainment |
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Customers aren’t adopting key features |
They don’t know about them, or they don’t see how they apply to their use case, or there are perhaps deeper product issues. |
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You’re relying on newsletters and mass emails |
You haven’t mapped how your customers prefer to receive and act on information |
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Your CRM says “Not the right time” over and over |
The value messaging didn’t land, or the problem you think you’re solving isn’t well defined |
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You’re unsure what customers think of your product today |
You’re flying blind — and missing critical signals for churn or growth |
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Expansion is happening through discounts or panic offers |
You haven’t created enough perceived value to justify a proactive investment |
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Expansion deals keep falling apart mid-cycle |
Your discovery process isn’t identifying blockers early enough — until it’s too late |