Upselling is one of the most powerful levers for growing your SaaS business. It’s not only a way to increase your revenue per customer, but also a way to boost customer satisfaction, retention, and loyalty.

But how do you upsell effectively without annoying your customers or coming across as pushy?

The answer is simple: you need to trigger upsell prompts at the right moments, when your customers are most likely to see value in upgrading their plans or features.

In this post, I’ll share some examples of how some of the best SaaS companies use upsell prompts to drive growth and delight their customers. I’ll also give you some tips on how to create your own upsell prompts that are relevant, timely, and helpful.

What is an upsell prompt?

An upsell prompt is a message that encourages your customers to upgrade their products or services to a higher tier. It can be delivered through various channels, such as email, in-app notifications, tooltips, banners, modals, etc.

The goal of an upsell prompt is to make your customers aware of premium features that they are missing out on or that could solve their problems better than their current plan.

SaaS Company Upsell Prompt Effectiveness
Slack "You've reached 10 integrations! Upgrade now for unlimited integrations." Very effective
Dropbox "Upgrade your Dropbox for more space and sharing features." Effective
Intercom "This series is ready to go live! To start sending it you'll need to upgrade your account." Moderately effective

For example:

  • Slack uses well-timed in-app messaging to turn free users into paying customers. For example, when a user reaches the limit of 10 integrations on their free plan (which happens pretty quickly if you use Slack for work), Slack shows them a message that says “You’ve reached 10 integrations! Upgrade now for unlimited integrations.” This message is relevant because it shows the user how they can get more value out of Slack by connecting it with other tools they use. It’s also timely because it appears right when the user hits a friction point that limits their productivity.

  • Dropbox uses persistent upsell prompts to remind users of their free accounts’ limitations. For example, when a user tries to upload a large file or share a folder with many people, Dropbox shows them a message that says “Upgrade your Dropbox for more space and sharing features.” This message is relevant because it shows the user how they can overcome their storage and collaboration challenges by upgrading their plan. It’s also persistent because it stays on the screen until the user dismisses it or upgrades.

  • Intercom doesn’t restrict the use of their series features but reminds the users that they have to upgrade to go live using well places tooltips. For example, when a user creates an email campaign on their free plan (which allows them to draft but not send emails), Intercom shows them a tooltip that says “This series is ready to go live! To start sending it you’ll need to upgrade your account.” This message is relevant because it shows the user how they can achieve their goal of sending email campaigns by upgrading their plan. It’s also helpful because it guides them through the next steps.

These are just some examples of how SaaS companies use upsell prompts effectively. But what makes these prompts work so well? And how can you create your own?

How to create effective upsell prompts

There are three key elements that make an upsell prompt effective:

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Relevance: The prompt should show the customer how upgrading will benefit them specifically based on their needs and goals. It should not be generic or irrelevant.
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Timeliness: The prompt should appear at the right moment when the customer is most likely to see value in upgrading. It should not be too early or too late.
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Helpfulness: The prompt should provide clear and actionable guidance on how to upgrade and what to expect after upgrading. It should not be confusing or misleading.

Here are some tips on how to create effective upsell prompts based on these elements:

Use data and feedback:

To make your prompts relevant, you need to understand what your customers want and need from your product. You can use data from analytics tools like Amplitude or Mixpanel to segment your customers based on usage patterns and behaviors. You can also use feedback tools like UserVoice or Hotjar to collect qualitative insights from surveys and polls.

Use triggers:

To make your prompts timely, you need to identify the best triggers that signal when your customers are ready or interested in upgrading. Some common triggers include:

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Reaching a limit: When a customer reaches a limit on their current plan (such as number of messages, integrations, storage space, etc.), you can show them an upsell prompt that explains how upgrading will unlock more features and benefits for them.
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Achieving a milestone: When a customer achieves a milestone with your product (such as completing a project, reaching a goal, getting positive feedback, etc.), you can show them an upsell prompt that congratulates them and suggests how upgrading can help them achieve more.
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Showing interest: When a customer shows interest in a premium feature by clicking on it, hovering over it, or searching for it, you can show them an upsell prompt that explains what the feature does and how they can access it by upgrading.

Use best practices:

To make your prompts helpful, you need to follow some best practices that will increase your chances of converting your customers. Some of these include:

  • Don’t get greedy: While upselling is a great way to increase revenues, it shouldn’t be treated as a shortcut to big profits. Avoid recommending a product or service that is significantly more expensive than the product being purchased. Instead, focus on offering value-added features that are relevant and affordable for your customers.
  • Educate the customer: Don’t assume that your customers know everything about your product or service. Use clear and concise language to explain what the premium features are and how they will benefit them. Use side-by-side comparisons, testimonials, screenshots, videos, etc. to demonstrate the value of upgrading.
  • Create urgency: Don’t let your customers procrastinate or forget about your upsell offer. Use scarcity tactics such as limited-time discounts, countdown timers, stock levels, etc. to create a sense of urgency and encourage them to act fast before they miss out on a great deal.
  • Personalize your recommendations: Upsells will look different for each customer—you can’t copy/paste your offer for everyone. Use data and insights to understand your customers’ preferences, behavior, goals, and pain points. Then, tailor your upsell prompts to match their needs and interests. For example, you can use their browsing history, purchase history, location, device type, etc. to show them relevant and customized upsell offers.
  • Limit the number of options: Don’t overwhelm your customers and cause paralysis by analysis. When you make an upsell offer, limit the number of options to two or three at most. This will make it easier for your customers to compare and choose the best option for them. You can also use labels such as “best value”, “most popular”, “recommended”, etc. to highlight the benefits of each option and guide your customers’ decision.

Test and optimize:

To make sure your upsell prompts are effective, you need to measure their performance and optimize them based on data and feedback. Some of the metrics you can track include:

  • Click-through rate: The percentage of customers who click on your upsell prompt out of those who see it.
  • Conversion rate: The percentage of customers who accept your upsell offer out of those who click on it.
  • Revenue per customer: The average amount of revenue generated by each customer who sees your upsell prompt.
  • Customer satisfaction: The level of satisfaction and loyalty expressed by your customers after seeing or accepting your upsell offer.

You can use tools such as Google Analytics, Hotjar, Appcues, etc. to collect and analyze these metrics. You can also use surveys, reviews, testimonials, etc. to get qualitative feedback from your customers. Based on the results, you can make changes to your upsell prompts.


Upselling is a powerful strategy to increase your sales and revenue without acquiring new customers. By creating effective upsell prompts that are timely, relevant, valuable, and persuasive, you can encourage your existing customers to upgrade their purchases and get more out of your product or service.

Upselling is not just about making more money. It’s also about building long-term relationships with your customers and providing them with solutions that match their needs and goals. By following the tips and best practices in this blog, you can create upsell prompts that are helpful, not annoying, and that will boost your customer satisfaction and loyalty.

If you want to learn more about how to create effective upsell prompts for your online store or SaaS product, you can check out our resources or contact us for a free consultation. We’d love to help you grow your business with upselling!