⚠️ Stop giving discounts to customers who would buy anyway

How Rippling actually does it

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Grammarly's recent acquisitions of Coda and Superhuman signal their ambition to build the ultimate workplace productivity bundle.

But here's the thing about bundling: when done right, it's an absolute superweapon for revenue growth. Rippling has used effective bundling to reach a $14 billion valuation, with the average customer adopting 7 different SKUs on day one.

The vast majority, however, make mistakes costing them millions in ARR.

 

Q: What's wrong with this Grammarly bundle concept?

Take a look at this bundle. Grammarly Pro ($12/mo) + Coda Pro ($10/mo) + Superhuman Business ($33/mo) = $55/mo retail. They're offering all three for $45/mo.

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The issue? Their $45 bundle only saves customers $10/month, which means you need to be a SuperFan of at least two products (including Superhuman) to justify paying for it.

Let me explain why this matters.

 

Definitions: Understanding Your Customers

When evaluating any bundle, you need to categorise potential customers into three groups:

  • SuperFans: Consumers who would (1) pay retail price for a product, AND (2) have the activation energy to actually go buy it

  • CasualFans: Consumers who lack one of those two SuperFan criteria above

  • NonFans: Consumers who assign zero (or negative) value to the product

 

Using Grammarly's bundle as an example:

  • A SuperFan would pay $12/month for Grammarly Pro

  • A CasualFan might think "grammar checking is nice, but not worth $12/month"

  • A NonFan doesn't see any value in AI writing assistance

Your bundle pricing determines which customer segments you're actually targeting.

 

The 9-Box Test

To evaluate whether a bundle makes sense, you line up SuperFans, CasualFans, and NonFans of each product on their respective axes. This creates a 3x3 grid showing you where the opportunity lies.

The goal of an effective bundle is to target the boxes where consumers are SuperFans of one product and CasualFans of another, or even CasualFans of both products who see enough combined value to purchase.

The box you absolutely DON'T want to optimize for? The intersection of SuperFans of multiple products. These customers would pay retail for each product individually anyway. There's nothing to gain by giving them a discount.

Unfortunately, this is exactly what most companies do when they bundle.

 

Q: So what should Grammarly actually price this bundle at?

The answer is below...

 

 

 

 

 

 

 

 

 

 

 

 

 

Here's the simple question "For how many products in the bundle do I have to be a SuperFan to justify paying for it?"

Let's apply this to Grammarly's bundle at $45/month:

  • If you're a SuperFan of Superhuman ($33), you still need $12 in additional value. That means you need to be a SuperFan of Grammarly OR Coda as well.

  • If you're a SuperFan of Grammarly ($12), you need $33 more in value. You MUST be a SuperFan of Superhuman.

  • If you're a SuperFan of Coda ($10), you need $35 more in value. This is impossible without being a SuperFan of Superhuman.

Grammarly's bundle has a SuperFan score of 2.

This is a high bar to clear. The bundle only appeals to customers who were already willing to pay retail for multiple products.

What matters most: pricing between 1X and 2X rounds the SuperFan requirement closer to 2 than you'd think. At $45 (down from $55), customers really need to understand and appreciate multiple products to see value.

The result? Companies who would gladly pay for one product at full price + get exposure to the other tools never convert because the mental math doesn't work.

What Grammarly Should Do Instead

To make this bundle actually effective at customer acquisition (not just retention), they need to hit a SuperFan score of 1:

  • Price the bundle at $33/month (the cost of Superhuman alone)

  • Now anyone who's a SuperFan of ANY single product gets the other two essentially free

  • CasualFans of multiple products suddenly see massive value

  • Finance teams think: "For the same price as Superhuman, we get Grammarly and Coda too? That's a no-brainer."

 

The Psychology Behind This

When bundling follows this approach, you're not just offering a discount to existing customers (who would buy anyway). You're creating a compelling reason for:

  1. Superhuman SuperFans to try Grammarly and Coda at no incremental cost (lowering customer acquisition costs)

  2. CasualFans of all three to finally commit because the combined value perception is massive

  3. Teams on the fence about any single product to justify the purchase by getting three tools

This transforms thinking from "Do we need all three products?" to "For the price of one, why wouldn't we get all three?"

That’s it for today. Again, if you’d like to see exactly how Canva, Stripe, and other unicorns optimise their funnels and get $25,000 in free bonuses, sign up to the ‘Welcome Kit Waitlist’. Welcome Kit Offer opens Nov 7 (limited 30-day offer).