Table of contents


  1. 01. Introduction
  2. 02. Why upselling works for you and your customers
  3. 03. Best practices for upselling
  4. 04. What messages should I be sending?
  5. 05. Customer spotlight: Announcing updates to different audiences at CloudSponge
The Upsell Messaging Starter Kit


We all know the business truism: it’s more expensive acquiring new customers than selling to old ones. New customers require more time, money, and handholding before they start to show steady returns. Old customers, on the other hand, don’t need to see ads, create an account, or go through the pains of installing your product. They just need to see the value of whatever you’re trying to sell next.

Good upselling is a win-win for both buyer and seller. It’s the act of showing your customers the value of new features, products, pricing plans, etc. when you believe it will help them be more successful at their jobs. When done right, upselling is not dissimilar to customer success. Most of us hate being sold to, but once it’s priced right we’ll buy almost anything that makes us more successful at our jobs.

Of course, the "snake oil” way to do this is to send untargeted, spammy emails your customers immediately label as “junk.” The better way to start a successful upsell conversation is through a behavior-based messaging campaign. When you know how customers are using your product, and in particular where they might be struggling, you can be hyper-specific about how you can offer more value to your customers.

Doing this is harder than sending a one-size-fits-all email blast hoping a customer bites. But it’s inherently better in the long run to be intentional with your customer messaging than to risk coming across as impersonal, tone deaf or greedy.

In this guide, we’ll share tips and templates so you can start sending upsell messages which work for both you and your customers.

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The Upsell Messaging Starter Kit

Why upselling works for you and your customers

Assuming you’re acquiring customers and showing them value early on, upselling kickstarts a self-reinforcing loop that benefits you and your customers.

The Upsell Messaging Starter Kit

Best practices for upselling

Look for positive signals

Don’t just reach out to every single customer six months after they’ve purchased to see if they want another ride on the merry-go-round. Spotting good upsell opportunities requires the same finesse you use to reach out to new leads.

If you owned Acme Messaging App, some positive indicators for growth could be if an account had: more than 10 teammates added; sent a high volume of messages; or had over 50% open rates on messages sent. (All this behavioral data can be tracked through Intercom). This means you’re messaging people who are likely to want or need the additional features you’re offering.

But look for red flags too

Successful upselling is all about finding the right customers. And that means having a clear idea who not to mesage. So if a customer of Acme Messaging App was sending a large number of messages, but getting average open rates of less than 10% and had multiple conversations with customer support over the past few weeks, then the upsell message is likely to fall on deaf ears.

Upsell in context

Triggering an upsell message within your product⁠ – at a relevant time and place⁠ – helps customers know and remember that a solution is readily available when their problem appears.

When you approach the limit of your available storage space in Dropbox, you’re prompted to upgrade each time you check the amount of free space available. And when your Dropbox is full, you can upgrade directly in the app.

Don’t be pushy

The key to upselling is not to be overly aggressive or pushy. As the old proverb goes, you can lead a horse to water, but you can't make him drink.

Continue leveraging the human, personal approach that got you the deal in the first place. Avoid “one-day only” and limited time sales gimmicks. There’s no need to twist someone’s arm into an upsell – if they want and need it, they will come to that decision on their own.

Don’t be impersonal

If you’ve ever received an upsell message that started with “Dear Valued Customer”, you know that it heads straight to the trash folder. At a minimum, your messages should communicate on an individual level. Products like Intercom can give you laser-focused insights into who your users are and what they are doing in your product so you can deliver truly personal upsell messages.

Your language choices can also have a big impact. For example: use words like “you”, “your”, and “yours” so customers can imagine themselves with the product.

Don’t wait until it’s too late

SaaS companies often wait until major milestones (e.g. one year since sign up) before attempting an upsell, only to hear “Sounds great. Actually, I could’ve used that 9 months ago.” If a customer has been successful to date, and is regularly displaying the right behaviors in your product, there is a valid expansion opportunity. Remember, renewal and expansion are part of the customer’s success too.

The Upsell Messaging Starter Kit

What messages should I be sending?

- email
In app
- in-app message

1. When they’ve hit a usage limit In app

“Freemium” has become the dominant business model amongst SaaS businesses today. Users get basic features at no cost and can access richer functionality after upgrading. And here lies the opportunity.

When someone has reached the usage limits for your product, you should automatically trigger an upsell message that outlines the increased value they will get from an upgrade. People, by their very nature, want what they can’t have, so they will be open to an upgrade provided they have a genuine need for more of your product in their lives.


Triggering an upsell message within your product⁠ – at a relevant time and place⁠ – helps customers remember that a solution is readily available when their problem appears.

2. When you announce a new product Email In app

In his book Marketing Metrics, Paul Farris shares a fascinating finding:

“The probability of selling to a new prospect is 5-20%. The probability of selling to an existing customer is 60-70%.”

Customers are much more likely to buy from a company they already trust than one they’ve never done business with before. With these types of messages, think of them less as a home-run and more as a jumping off point to start a deeper conversation with your customers. Often, they just don’t know that other options exist, or they don’t clearly understand what these additional products do and how it could improve their existing way of doing things.


If your announcement message is more than
 a few sentences, go for an email rather than an in-app message. Rarely is it necessary to interrupt your customers' workflows with a marketing message.

3. To move them to a better price plan In app

When you’re building a business based on recurring revenue, what you want is predictability. Getting more of that recurring payment upfront reduces churn and improves cash flow, letting you spend more money now to acquire customers faster.

So instead of thinking of your plans as different payment options, think of them as a feature you can upsell. For example, if you have a monthly price plan, set up a message that asks those on a monthly plan to switch to annual a few months into their subscription. This will improve your cash flow in the short term and boost your customer retention in the long-term.


The context of this message really matters. With an in-app message, the annual offer is present smack bang in the middle of the user soaking up the value they get from your product. In fact, Baremetrics saw a 30% increase to annual plans when they used in-app instead of email.

4. When they’re using a feature a lot In app

Another effective trigger for your upsell campaign is when your customers have achieved a milestone with your product. Such as:

  • Spending over a certain number of hours in your app
  • Accomplishing a certain number of tasks in your product
  • Logging in a certain number of times
  • Installing particular integrations or add-ons

Use these events as opportunities to remind your customers about the value they’re getting from doing business with you and think about how you can upsell them now to take things even further.


Emojis/GIFs keep the tone of these short in-app messages lighthearted and fun. In one of our messages, we saw many more responses when we included a GIF in the message that celebrated the customer’s milestone achievement, compared to the test without a GIF.

5. When they’re getting results from your product In app

Just because a customer is doing lots of something doesn’t necessarily mean they’re getting value from your product. For example, I might have sent 10,000 messages with a marketing automation tool but if my open rate was 1% and my conversion rate lower still, I’m unlikely to invest further in the product.

The best candidates for an upsell are customers who have passed one or more “success milestones”, the point at which they’ve received tangible value from your product. For example, if you sell software to build ecommerce stores, a milestone could be “customer makes first sale”.

As your customers achieve various success milestones along their journey, their willingness to invest in your company goes up, and it is up to you to recognize that and take advantage of it.


As every customer will have a very different definition of success, use these messages to initiate a conversation rather than try to close a deal. These are valuable customers so proceed with caution.

6. When other customers are seeing success Email

American showman P.T. Barnum shared a piece of advice every business needs to take on board: “Nothing draws a crowd quite like a crowd.” Sometimes people just need to see what others are doing to convince them to take the next step.

Let’s say you have a subset of customers on a free plan, while others are on a premium plan. Why not message your free customers and show them how your premium customers are succeeding with your product? Many will just need to see results in action to be convinced to take the next plunge. At worst, they’ll get the social validation that countless businesses just like them are getting value from your product.


Tailor your message based on information you have about a customer. For example, if you’re trying to upsell a finance app, send them examples of similar finance apps you’ve helped be successful. Seeing their competitors using your product successfully is the single best way to increase FOMO.
The Upsell Messaging Starter Kit

Customer spotlight: Announcing updates to different audiences at CloudSponge

By Jay Gibb, CEO of CloudSponge

At CloudSponge we recently released the biggest update in our company’s 9-year history. We used Intercom Messages to tailor our announcement message to different segments of our customer base, which drove unexpectedly high adoption rates.

For previous updates we’d blast the same email to everyone, from our earliest customers to those who’d dropped out after their free trial. But there’s no good way to write something that’s applicable to everyone. First we identified different audiences, and then used Intercom to segment, create, and send the messages. Here are two of our most impactful ones:

Customers with grandfathered pricing

In terms of revenue potential, this was our most valuable group. For this group the challenge was showing the value of the update and convincing them that it would be worth the additional cost:

Leads who completed a free trial

The second segment included those that completed a trial, but failed to convert to paid accounts. For this group the goal was simply to make them aware of the new features and offer an extended free trial to encourage adoption.

The first sign of success for the targeted campaign were the email open rates: 32% for customers on grandfathered pricing, and 42% for leads who completed a free trial, both substantially higher than average.

We expected that moving all of our grandfathered customers to new plans would take a year. But with Intercom’s help, we had 20% of them upgrade on the first day. The 20% of grandfathered customers who upgraded now pay between 2 to 4 times more per month, and represent nearly 18% of our entire customer base.