12 Real-World Upselling Examples in SaaS for Inspiration

Userpilot Team
10 min readSep 30, 2024

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Upselling SaaS means driving more revenue and increasing the customer lifetime value through subscription upgrades and add-ons. When your product has a freemium version or a trial, upgrading free users or free trial users to paid accounts is also considered an upsell.

When done well, upselling can help boost sales and, of course, customer retention as users continue to use your product.

So, how do SaaS companies upsell? In this article, we’ll cover a list of real-world upselling examples and effective techniques to kick-start the user upgrade process.

Best upselling examples in SaaS for strategy inspiration

You’ll find many SaaS business examples of how to upsell customers. But do all of them end in successful upselling? Short answer: no. So, here are the best 12 upselling examples that have proven effective for helping big organizations encourage customers to increase the average order value.

ClickUp drives upsell by gating high-value features

ClickUp strategically lists premium features in the navigation menu. When a user gets to a feature they can’t access (“Audit Logs”), ClickUp doesn’t just block them. Instead, it uses this as an opportunity, telling the user, “That feature isn’t available on your current plan.” This immediately creates a sense of wanting what they can’t have.

The upsell invitation features:

  • A list of the benefits of both the premium feature and the upgraded plan.
  • Clear CTAs, like the “Upgrade to Enterprise” button, that encourage immediate action.
  • Alternate action options, like the “Contact Sales” button for users who might need more information or have a complex buying process.
  • Reduced risk with the “100% money back guarantee”, boosting user confidence in the upsell.

You can use such upsell ideas when your product offers tiered pricing models and there are additional features on higher-priced plans.

ClickUp upsell example
ClickUp: Gated features for boosting upsells.

Dropbox and its continuous reminders

Dropbox takes a proactive approach to upselling by consistently reminding customers about the benefits of upgrading their plans for additional space. This keeps the upgrade top-of-mind, ensuring users are aware of their options at all times.

This upselling strategy features:

  • An engaging graphic to draw users’ attention.
  • Focused CTA (“Try it free”) that’s concise and straightforward.
  • Simplicity, with minimal words communicating the problem and solution.
  • Proactive engagement, addressing customer’s evolving needs before they feel constrained by the limitations of their current plans.

This approach applies to products with usage-based limits or flows where you can anticipate friction points in the user experience.

Dropbox upgrade reminders
Reminders keep the upsell top of mind.

Intercom creates a friction point to nudge the upgrade

Intercom doesn’t restrict the use of its “series” feature. However, once users are in the message creation flow and go to publish the series, the set live options are locked behind the Pro plan — an intentional friction point.

Here are the elements from Intercom’s example that make such upselling techniques work:

  • Good timing, upselling once users have already experienced the product’s value and have a strong reason to upgrade.
  • Sense of investment, since users have dedicated ample time to the feature by this point. This makes them more inclined to pay for access.

This upsell process is effective if your pricing is feature-based, so creating an intentional friction in the flow for that feature makes sense.

Intercom upsell example
Use friction points for upsell prompts.

Loom creates a sense of urgency to drive upsells

Loom’s upsale or upsell prompt highlights the time-saving and quality-enhancing benefits of its AI features.

Sounds pretty simple, so why does it convince customers? Here are the elements that make it work:

  • Time-bound discounted price of a valuable feature, creating urgency to act quickly by mentioning “Buy before prices increase next month.”
  • Video tutorial visually demonstrates the feature’s value, increasing users’ understanding of why they should upgrade.

Increase sales with this technique by using it during product launches or promotional events to emphasize limited-time discounts on valuable features.

Loom's upselling example
Urgency helps with upselling.

Miro employs feature restriction to prompt upgrades

Miro tries to upsell customers by displaying a prompt right when users go to create a new board. The prompt explains how users have reached their plan’s limit. If they create a fourth board, their existing boards will become view-only.

While this may seem to hinder the customer experience, it works because this upsell includes:

  • Fear of losing an important feature by highlighting the immediate negative consequences of a lower plan. This makes users more likely to upgrade to retain essential functionality.

This technique is most effective when users are actively engaged in critical flows and approaching their plan limits.

Miro's upselling example
Restrict certain features to prompt upgrades.

Pendo leverages customer data to trigger a relevant upsell

Pendo’s upsell features an in-app pop-up introducing a relevant feature to users and asking them to either schedule a demo or be reminded of the feature later.

Simple, but it works because it includes elements like:

  • Personalizing messaging based on user behavior and customer data.
  • Triggering a demo offer only for features available in the Pulse and Ultimate plans. So, customers interested after the product demo may consider upgrading, increasing the average order value.
  • Moving prospects down the sales process by connecting them with a salesperson rather than prompting an immediate upgrade. This lets customers experience the feature’s benefits, so they’re more likely to upgrade.

Try such upsell ideas on engaged users who frequently explore advanced features but haven’t yet made the move to a higher plan.

Pendo upselling demo offer
Pendo’s demo offer for upselling.

Zapier implements trial countdown banners to push upgrades

Zapier encourages customers to upgrade anytime by constantly providing a visual reminder through their in-app banner.

The upsell example features:

  • A countdown, i.e., “You have 14 days to try Zapier’s paid features”, adds a sense of urgency to act quickly or miss out.
  • The concept of frequent exposure dictates that the more customers are reminded about the upgrade option, the more they’ll want it. That’s why even subtle strategies like this increase upselling and cross-selling conversion.

Implement this technique if you notice consistent product usage among customers but no commitment to higher-tier plans.

Zapier's upselling example
Zapier’s banner countdown for upselling.

Canva uses a downgrade reminder to reinforce upgrade necessity

Once a specific trial ends, Canva shows a downgrade prompt that states how many times the user utilized specific premium features. Plus, it offers a low-commitment way to re-experience premium features and potentially re-evaluate the need for an upgrade.

This upselling technique features:

  • Relevant trial offers. For instance, users no longer part of an education team plan can either opt for an individual trial experience or re-experience the education plan.
  • Leveraging psychology, it taps into the human tendency to value things only when you’re about to lose them.
  • Reminding users of the value they experienced, Canva successfully encourages them to reconsider upgrading, thereby boosting customer lifetime value.

Use this upselling strategy when trial users frequently utilize premium features but don’t convert after their trial ends. Similarly, if existing customers hit limits on basic plans, remind them of the premium features they previously benefited from.

Canva's upselling prompt
Downgrades help make upgrades essential.

Grammarly offers limited premium feature usage to drive upgrades

Grammarly allows users to try the premium version three times per day, enabling them to easily experience its benefits while editing documents. Once the premium feature limit is reached, an upgrade prompt pops out.

This upselling example proves effective because of elements like:

Use this technique when users frequently hit the premium feature limit, signaling high interest in upgrading. Similarly, offer limited premium feature usage during user onboarding to familiarize new customers with the benefits of these features.

Grammarly's upselling example
Grammarly upsells by limiting premium feature use.

Asana promotes paid features to power users offering them trials

Asana successfully increases customer lifetime value with its upsell strategy of showing off premium features and their benefits to certain user segments.

Upselling examples like Asana’s work because they include features like:

  • In-app modals are effective for grabbing attention during critical user flows and providing clear prompts.
  • Additional support resources via the “Learn more” button for users who want to explore further before committing.
  • Effective segmentation and targeting based on user behavior and interests, ensuring the maximum likelihood of successful upselling.

Try this upselling technique once you identify specific user segments, like power users, that demonstrate high product engagement and interest in premium features.

Asana's upselling example
Asana’s in-app modal for upselling.

Airtable combines in-app message upgrade prompts with emails

Airtable pairs its in-app prompt with engaging email marketing to create a highly effective upselling strategy. It uses emails to connect with users outside the app through its newsletter.

This innovative upsell features:

  • An informational newsletter provides new customers with a breakdown of a few of Airtable’s premium options to build interest.
  • Relevant suggestions on how to get the most out of the product, offering proactive support to improve customer satisfaction.
  • Complements in-app messaging, knowing that it may be great for communicating but only when your customer is inside the app.

This method is great for re-engaging disengaged users who previously showed interest in your app but haven’t used it recently.

Airtable upselling email
Airtable upsells using email marketing.

Spotify uses a contextual pop-up to encourage upgrades

Instead of waiting for customers to visit their pricing page and learn about additional pricing plans, Spotify does it the other way around. It allows free customers to skip six tracks per hour, and then they’re prompted to upgrade to premium.

This upgrade invitation features:

  • Timely prompts that are presented right when the user hits a feature usage limit but clearly needs it.
  • Premium features built into the user experience, so users get to see them in context and understand how they will benefit from them.
  • Frequent strategically positioned reminders that keep the upgrade top-of-mind for users.

Use this approach for users who frequently engage with your free product but don’t explore pricing plans.

Spotify upselling examples
Spotify’s contextual upgrade prompt.

Common upselling techniques to increase sales

  • Plan upgrades: Use banners, tooltips, or modals to encourage users to switch from a lower-tier to a higher-tier plan, highlighting the benefits of enhanced features.
  • Feature add-ons: Implement tooltips or modals to suggest additional features or functionalities that can be purchased on top of a customer’s existing plan. E.g. Surfer’s extra AI credits.
  • Usage-based upselling: Utilize modals to notify customers when they reach usage limits, prompting an upgrade for additional capacity or features. E.g. Loom’s five-minute recording limit.
  • Renewal upselling: Provide upgrade options or additional features add-ons during subscription renewal reminders.
  • Personalized upselling: Present tailored upgrade offers based on users’ past behavior and usage patterns, as seen in the Pendo and Canva examples above.
  • Education upsell: Provide customers with educational resources or demo content that highlights the value of upgrading or adding features. E.g., Pendo’s demo invitation, as discussed above.

Create upgrade prompts and target the right users with Userpilot

Are you looking to implement any of the upselling tactics described in this article?

You can use segmentation capabilities to ensure your in-product messages show to the right user at the right time.

You can build modals, slideouts, tooltips, and banners and target customers contextually with your upgrade messages.

Userpilot's demo offer builder
Trigger demos for certain segments with Userpilot.

Use product experiments and split-test your in-app messaging to optimize results and improve important SaaS metrics such as expansion MRR rate.

A/B test results
Run A/B tests with Userpilot.

Userpilot makes it easy for your SaaS business to generate expansion revenue by creating upsell opportunities and prompting upgrades without writing a single line of code.

Frequently asked questions about upselling examples

Let’s go over some additional insights to help you fully understand everything about upselling and cross-selling techniques.

What are good examples of upselling?

Here are some effective upselling examples for various industries:

  • SaaS: Convincing users to upgrade to a premium subscription for advanced analytics.
  • E-commerce: Suggesting a larger size or a bundle deal at the checkout page.
  • Travel: Offering room upgrades or additional amenities during the booking process.
  • Retail: Proposing a protection plan for gadgets, emphasizing the peace of mind it provides.

What is an example sentence for upselling?

Definition: Upselling involves encouraging customers to purchase a more expensive item, add-on, or upgrade instead of their initial choice.

Example sentence: “During the software demo, the sales representative suggested upgrading to the enterprise plan for enhanced features and better support, rather than just purchasing lower-priced related or complementary products.”

How do you upsell customers?

Here’s how you successfully upsell customers:

  • Know your customer: Understand their needs and preferences.
  • Timing: Suggest upgrades at the right moment.
  • Highlight benefits: Clearly explain the advantages of the upgrade.
  • Offer trials: Provide limited-time access to premium features.
  • Handle objections: Address any user concerns or questions.
  • Personalization: Use customer data to tailor upsells.

Conclusion

What’s one thing all these 12 upselling examples have in common? They follow the fundamental rule of successful upselling — to offer customers greater value if you want them to give you more money.

By using tactics like gated features, timely reminders, and personalized offers, you can easily turn pushy upsells into a seamless part of the customer journey.

Want to get started implementing these upselling strategies? Get a Userpilot demo and see how we can help you discover upsell opportunities to boost customer lifetime value.

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Userpilot Team

Userpilot is a Product Growth Platform designed to help product teams improve product metrics through in-app experiences without code. Check out userpilot.com