“Would you like to upsize your fries?”

That’s an upsell, but that’s not the kind of upsell a Customer Success Manager would normally handle. 

In the CSM’s case, the conversation would go:

“Would you like to upsize your fries?”

And the customer would go:

“Would that help me hit my weight goal? Why don’t you just offer a larger size to begin with? And why would I upsize my fries when you didn’t even put enough salt on them? And Burger King is offering to upsize my fries and my drink for fifty cents.”

As you can see, upselling as a CSM has a few unique challenges. Yet the majority of CSM’s aren’t trained sales people. Is it still possible to upsell a customer without triggering an unintentional backlash?

Absolutely! And we’re here to show you how.

1. Understand the customer’s goals

The best way to pitch an upsell is by aligning it to the customer’s goals. 

You should already know this if you’re the one that onboarded the customer the first time, but it doesn’t help to double-check. Their goals may have changed, and you don’t want to pitch based on old information. 

It helps if you’ve already set up trackable and measurable goals for your customer. These indicators of success will provide you with additional data points for making your case. If you don’t have trackable goals in place, data-based or stage-based milestones will do in a pinch. 

2. Find out if there’s a real upsell opportunity

Not all upsells are created equal. Just because a customer could purchase your upgrade, doesn’t mean they should. 

You’ll quickly find that not all of your customers are interested or qualify for the upgrade that you’re trying to push. 

In startup terms, consider the difference between market size and addressable market. You might have 500 customers that could potentially purchase your upsell (market size), but in reality it’s only going to be useful to a fraction (addressable market). 

If you discover that your customer isn’t likely to benefit from this upgrade, stop. Do yourself and your customer a favor and move on to someone else. 

3. Use customer data to inform your pitch

Don’t pitch your customer blindly. Learn as much as you can about how the customer is currently using your product before you approach them. That way, you’ll be able to align your pitch with their pain points and make the upgrade more attractive. 

Consider reviewing the following data:

• Current and previous support tickets
• Usage data
• Onboarding KPIs and performance metrics
• Notes from previous conversations with your team

It may take some time to pull all of this information together, but it’s worth the effort if you can strengthen your upselling position.

4. Pitch outcomes, not upgrades

Upselling to an existing customer follows the same principle as selling to a new one - pitch the outcome, not the feature. 

It’s way too easy for CSM’s to fall into the habit of explaining the details of an upgrade’s functionality - how it operates, not how it helps.

Take a page from the sales team and focus on what the upgrade will do for them. Align this outcome with the customer’s goals, as we mentioned before. You have an advantage here, because you’re already working closely with this customer and should have a good understanding of what is important to theme.  

5. Time your pitch carefully

Timing, as they say, is everything. Your pitch will go as smoothly as skiing on fresh snow if you can pick the right moment. 

This requires knowing exactly what is going on with the client’s account. You have to research based on your own data, as we mentioned in the point above, but you also have to be alert for the perfect opportunity to pitch. ‍

Pitch when something significant happens. Did the client just launch SFDC internally? This may be a good time to upsell them on an SFDC integration. You could also pitch them after a significant milestone, like say upon their one-year anniversary with your company.‍

Pitch when they’re happy. Is the client basking in the luxury of having a working software platform? Did your QBR go swimmingly? Then you might want to upsell them on a new feature you’re about to release. They’re going to be so happy with their initial launch that they’ll be eager to see what else you can do for them.‍

Pitch when you get a win. You can most definitely follow-up a win with a pitch. The customer will more than likely be in a good mood thanks to a major accomplishment like finally finishing the onboarding process. 

Just make sure your win is significant. Don’t over inflate the importance of mundane accomplishments just because you need an “in.”‍

Pitch when they need it the most. The customer has a big, BIG problem. Then here you come, swooping in like a superhero armed with just the right feature to save the day. All they need to do is fork over the money, and they fall over themselves thanking you!

Except they don’t. 

Think about it from their perspective: there they are, unable to get the report they want out of your platform, and you show up and offer an “Upgraded Report Bundle” for way more money. It almost feels like you’re making them pay extra for something your product should’ve already had in the first place! 

Be very, very careful how you approach situations like this. Yes, it’s a perfect upsell situation, but if you handle it wrong you could be seen as an opportunist. 

6. Give transparent price estimates

You’re already asking the customer to pay additional money to use a product that they already paid for, so the least you can do is tell them what exactly they’re going to get.

Give transparent pricing information as well as a thorough breakdown of what the upsell involves. Explain the process of upgrading their product and whether or not you need to conduct any training, orientation, or demonstration for best results. 

7. Price your upsell reasonably

Now, I realize that you may not have total control over pricing when you’re upselling a customer. But if you have the freedom to present the customer with multiple choices, try to lead with options that won’t give your customer sticker shock - even if they can afford it. 

The sheer psychological impact of seeing a $299-a-month product jump to $999-a-month would be enough to give anyone pause. Worse still, such a jump may frighten the customer into reconsidering your entire arrangement. 

8. Be flexible

Your customer might not be immediately won over by your upsell offer (I know, it’s quite a shock). 

If they waffle, be flexible. Change your approach based on their objection. There are a bunch of things you can try:

• If they have a different need, change your offer from an upsell to a cross-sell. Or maybe package the two together in a bundle.
• If they object based on price, negotiate the amount (with approval from your manager) or offer them a cheaper option.
• If they are skeptical of the upgrade’s value, offer a trial period.

Don’t get hung up on the offer as it is written. Find a solution that works best for the customer, just like you would during their onboarding. 

9. Deliver value quickly

Don’t let your customer feel buyer’s remorse at any point in your relationship. Not before the upsell, and not after. 

You’re an awesome CSM (I hope), and you should’ve already helped the customer obtain value from their initial purchase. They trust you, which will help grease the wheels and make the customer more likely to connect with your upsell pitch. 

Now you have to do the same thing with what you’re upselling. Your job doesn’t end when they pay for the upgrade, just as it didn’t end when the customer signed their initial contract. On the contrary; it’s just beginning. 

You pitched them on what benefits they would get, and now you have to prove that it wasn’t all talk. Conduct trainings, give homework, work with their admins... the sooner the customer sees value from their upsell, the better. 

10. Protect the relationship

This is the last and most important tip I can give you. Upselling can be a high-risk move, especially if the directive comes from managers who don’t have the appropriate perspective. Either that, or they only care about the numbers and not the relationship. 

It’s your duty as a CSM to stand firm against internal pressure if you know that attempting to upsell is going to sour your customer relationship. Protecting the relationship is paramount. 

But don’t just tell your manager that it’s a bad fit; tell them why it’s a bad fit. Give them the context so that you can either: 

• plan a different approach
• get the customer to a state where they are fit for the upsell, 
• or skip this opportunity in favor of a more suitable promotion later on.

This will help you stay in both your customer’s and your manager’s good graces. ‍

Need more information on how CSMs can drive value for both the customer and the business? Check out the rest of our blog for more great tips.‍