Falling behind on Upsells?

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Hey CS Pro,

If your upsells feel more like a pitch than a no-brainer next step, your storytelling muscle might need a workout.

In this episode, I’m breaking down how mastering the art of storytelling can make upselling feel easy, natural, and actually valuable to your customers.

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Why Your Upsell Strategy Isn’t Landing

Let’s cut to it. Data and decks aren’t enough anymore.

You can walk into a QBR with perfect health scores and usage stats. But if you can’t help your customer feel the value, your upsell won’t stick. Why? Because humans respond to emotion. They connect with stories, not spreadsheets.

And that’s the biggest trap I see CSMs fall into. You’re so focused on the what… metrics, charts, timelines… that you miss the why. Why it matters. Why now. Why should they care?

If you’re not telling a compelling story, your upsell is just another sales pitch.

The 5-Step Storytelling Framework You Need

Here’s the framework I use (and teach in RevUp Academy) to turn flat pitches into powerful narratives:

1. The Before: What was broken before your product came into the picture? Think back to that onboarding or sales call. What pain were they solving?

2. The Trigger: What changed in their business that made them seek out your solution? A merger? Missed targets? Growth?

3. The After: This is your spotlight moment. What’s better now? Wrap usage metrics in emotional outcomes. What feels easier, smoother, or more successful?

4. The Future Chapter: Now introduce the upsell. Not as a pitch, but as the next logical chapter. More licenses? Added support? Frame it as the natural evolution of their success story.

5. Social Proof: Sprinkle in a short, relevant story from another customer who took that same step and saw great results. Keep it punchy. Keep it relatable.

It’s that simple. And when you write it down and practice it out loud, it starts to click. It becomes a conversation, not a pitch.

Your Weekly Challenge 

This week, here’s your challenge. Choose ONE customer with an upcoming upsell opportunity.

Now, grab a notebook and write out their story using the 5 step framework above. Don’t overthink it. Four to five bullet points max.

Then, say it out loud. Practice your tone, pauses, and transitions. Because here’s the truth. The best CSMs rehearse like they’re in sales. And storytelling? It’s your new script.

You’re not just selling a feature. You’re guiding them into chapter two of their success story, with you as the trusted partner.

When you frame your upsell as their next win, it doesn’t feel salesy. It feels smart.

Takeaways

1. Stop leading with data

Data is important, but stories move people to take action. Use both. Together.

2. Your upsell is the sequel

Don’t drop it in like a plot twist. Build the momentum through the customer’s journey, and make the upsell the next logical chapter.

3. Practice makes confident

Write out your customer’s story. Then practice telling it. Confidence comes from repetition. Not magic.

🔦 Free CS Resource Spotlight 💡 

That’s it for this week! If you want to hear all of my tips on storytelling and how I can help you improve your storytelling by 200% in just 20 minutes, then check out the full podcast episode on your favorite player below.

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Cheers to your CS success,

Anika

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