8 Upselling Examples from B2B and B2C companies: Why They Work

8 Upselling Examples from B2B and B2C companies: Why They Work

Users can access Spotify’s extensive music library for free, yet their Premium subscriptions grew 15% in 2022

Meanwhile, ecommerce marketing software Privy is generating 10% higher average order value for Shopify users with their related product recommendations add-on.

These tactics are upselling and cross-selling (respectively). While both effectively drive revenue and enhance the customer experience, upselling is ideal for companies with a single product or freemium model.

In this article, we’ll show you how six companies employ the best upselling strategies. Then we’ll tell you how to do it yourself so you’re not leaving money on the table.

1. How Calendly deploys FOMO

It’s hard to sell customers on something they don’t know they need. Sometimes users need to experience your product, get a feel for it, get invested in it, before they’re convinced they want it.

Furthermore, upselling doesn’t exclusively occur at checkout. It’s not about selling additional products (this is cross-selling), nor is it only for selling more expensive items to happy existing customers. 

In Calendly’s case, the scheduling tool’s upsell is teased for new customers in the free trial stage.

Screenshot of Calendly Free Trial Features

Calendly uses a freemium model, offering a free tier and encouraging users to upgrade for access to advanced features.

The company has cleverly powered growth (to the tune of $3bn) with upsells in the earliest stages of the user journey.

Instead of waiting for users to need their advanced features, Calendly gives access to everything for a limited time.

This works like test driving a car, playing on two unconscious psychological biases called the endowment effect and loss aversion. The endowment effect causes us to value items that we already have higher than those we don’t have. 

Loss aversion explains why we fear losing something more than we enjoy gaining the same thing.

In the case of Calendly, once users become used to having these advanced features (such as creating multiple calendars or scheduling by priority) they’re less likely to want to give them up. 

Likewise, users will feel inclined to avoid giving up the features (more so than they would feel inclined to sign up to get them without having first experienced them).

Calendly helps their users see the value in their advanced features by giving them free, full access straight away. It then reminds them when they’ll lose those features if they don’t choose to upgrade.

Screenshot of Calendly Billing Page

If you’re growing a freemium SaaS company, consider offering access to your full suite of features upfront. Demonstrate to users how your product can help them solve problems and fulfill jobs to be done (JTBD) by allowing them to try it themselves.

Once this trial is ended, remind them of the features they’ll lose once the trial is over. Include this in your reminder email marketing, offering a call-to-action to subscribe early.

2. How WeTransfer makes things simple

On the other hand, your customers might not be interested in all the bells and whistles you offer. In fact, forcing new customers to learn the full functionality of your product before an offer expires might create friction and frustrate them.

If you’ve learned through customer research that your buyers are busy people, simplifying their lives and saving them time might speak more to their needs than lifting the hood on your tool.

In this case, stick to one winning message.

Dave Trott reflected on his work under John Pearce, echoing a similar message:

“If I throw six tennis balls to you, you won’t catch them all. You may catch one, but the chances are six to one against you catching the most important one. In advertising we know you can only catch one message. So, it’s our job to decide which is the most important message and only throw that one.” – John Pearce as told to creative director and author Dave Trott [via MarketingWeek]

Like Calendly, file sharing service WeTransfer uses a freemium model: a free plan offering limited features with premium features unlocked in a paid plan.

WeTransfer doesn’t sleep on its free plan users, hoping they’ll one day discover its Plus plan. The platform encourages current customers to upgrade to their paid “Pro” plan in a simple upsell email.

Screenshot of WeTransfer Upsell Email

WeTransfer doesn’t go for the hard sell. Neither does the platform list all the features users can get by upgrading. 

WeTransfer highlights one main feature with one smaller feature mentioned below. 

This simplicity is also echoed on their pricing page:

Screenshot of WeTransfer Pricing Page

Each plan highlights a maximum of three features. If users want to read more, they can “jump to more features” below.

This is a great strategy to simplify the journey for customers. Not all customers need to see everything you offer at first glance. This can add to their cognitive load, driving them away by overloading them with information.

As mentioned above, this is worth considering if your audience is busy. In WeTransfer’s case, they know people who want to transfer large files (and who might be interested in branded backgrounds) are likely to be busy professionals.

Instead, highlight your most important features (backed up by your data), limiting to around three.

According to academic research by Shu and Carlson, when it comes to persuading people to accept claims about a product or product features, three is the magic number. After three items, attitudes toward the item begin to drop and skepticism sets in.

Screenshot of Results from Shu and Carlson’s (2014) study

This finding explains why three tends to be such a favorable number in marketing. In the experiment, the researchers tested several variations of marketing statements with a range of numbers of claims.

Respondents felt less favorably toward products with more than three claims, such as this one about shampoo:

“Makes hair cleaner, stronger, healthier, softer, shinier, and fuller.”  

The researchers determined that when trying to be persuaded, customers become more skeptical the more claims they see. Essentially, customers start to think the quality dips with each additional feature.

Stick to a single message where possible. And avoid overwhelming your audience with too many claims. They’re either too busy to cope, or they won’t believe you.

To incorporate lessons from WeTransfer in your upsells:

  • Look at your data and determine the single, most important message for your audience
  • Identify the top three features of your tool and highlight them
  • Don’t overwhelm a busy audience with all-access

3. How Squarespace plays on emotion

Emotion is a powerful marketing tool. It can be used to manipulate, but it can also motivate audiences to reach their goals. 

Website creation platform Squarespace plays on the latter. Squarespace is a free website builder, but if you want to connect a domain and launch, you’ll need a paid plan.

This means that users will sometimes sign up, start building a website, and never convert.

When that happens, Squarespace sends out a series of emails:

Screenshot of Squarespace Start of Trial Email

And this one:

Screenshot of Squarespace End of Trial Email

Squarespace knows its audience of creators is busy, and likely distracted. Instead of accepting their conversion rate and cutting their losses, the platform reminds users why they started their website in the first place.

The platform’s emotive email copywriting is intentional. While people often think they’re acting on logic, emotions play a key role in decision-making.

Researchers have demonstrated repeatedly that we choose brands and take action based on those we like, those we trust, and those we connect with (including through storytelling). 

People particularly like it when brands empathize with their needs and problems. Squarespace demonstrates their understanding of user goals. Instead of coming from a position of “seller with a product,” Squarespace communicates that they want to help their users accomplish what they set out to do. 

To connect with customers on an emotional level, get to know your customers’ needs. Understand which pain points they’re itching to solve.

When creating your messaging, show how your solution helps them solve these problems. Paint a picture of how you’ll lead them from their current state to their desired state. Use message testing to get qualitative insights and ensure you’re resonating with your audience.

4. How Google Drive uses urgency

Similar to following up with leads, audiences using a free or lower-tier version of your product might need reminding that your premium offers exist.

Plenty of studies show that people are unlikely to act unless reminded (here’s one, for example). The balance lies in staying top of mind without pushing customers away.

Google Drive reminds free plan users that the storage across their workspace is limited. And it does so with a constant visual reminder at the side of the Drive dashboard:

Screenshot of Google Drive

A subtle visual reminder with a CTA button is all Google Drive uses to show its users how much storage is left. Once they start getting close to the end, the message turns from blue to red, using design to create a sense of urgency

Screenshot of Account usage numbers in Google Drive and Gmail

Users also receive top bar notifications and emails so their service isn’t disrupted if they run out:

Screenshot of Google Drive Running Low on Storage Notification

Google Drive isn’t pushy. It offers opportunities to clear more space alongside their upgrade CTA.

Google Drive has found a balance. It doesn’t lambast users with notifications and its visual reminder reinforces the message (“you’re running out of storage, so you probably want to buy more”).

Does your product offer a free plan? Emulate Google Drive’s approach by reminding your product of its limitations. This could be resource-based (such as storage and “credits”) or feature-based, providing a call-to-action for users to upgrade their plan.

5. How Zapier puts their data to good use

Customers love it when you can personalize their experience. If it encourages users to take an action that adds to your bottom line, even better.

Way beyond using merge tags in your emails, effective personalization involves knowing your customers and using their data to serve them better.

Zapier uses personalization to monitor when users are coming to an end of their trial. If they’ve engaged with their tool over a certain threshold, users receive this email:

Screenshot of Zapier End of Free Trial Notification

This is a genuinely useful email for users. They can see clearly how much of the tool they’ve used, knowing that at this rate, they’ll run out of free “zaps” before their renewal.

The email also tells them which services they’ll lose access to that they may have used during their trial.

The data makes Zapier’s upsell helpful and informative. It appears to come from a place of assistance, rather than revenue generation.

Take your user’s behavior and apply it to your upselling efforts. Illustrate the value they get from your product using cold, hard data. If a user has saved 10 hours per week by using your tool, quantify and communicate this to them.

Personalize your messaging further by segmenting based on how invested they are in a product. For example, if a user still hasn’t reached an “aha!” moment, offer a free consultation that walks them through how your product will solve their specific problem.

6. How HelloBar makes themselves indispensable

Humans are creatures of habit—and habits are difficult to quit. It’s why we pick up our phones anywhere between 58 times and 344 times per day.

Meditation brands like Headspace and Balance have cottoned on to this with daily reminders about their practice.

Screenshot of HeadSpace Daily Reminder notification on Phone

Pop-up tool Hello Bar encourages users to build a habit around their app by becoming indispensable. 

Tracking the progress you’re making toward your goals can be highly motivating. Hello Bar gives its ecommerce users performance stats to increase stickiness and use the app more often, building up habitual use. 

Screenshot of Hello Bar Mobile App

Once users are engaged, upgrading offers a friction-free way to continue enjoying their tool (no ads, personal branding, more statistics, etc.).

To incorporate lessons from Hello Bar in your upsells:

  • Measure and share performance metrics
  • Help users build your tool into their habits through reminders and notifications
  • Offer engaged users an upgraded experience 
  • For physical products, highlight how more expensive versions can reduce friction in their daily lives


Upselling is a mutually beneficial sales technique. It increases your average order value and customer lifetime value, while also giving customers a better experience or higher quality of service.

As with any move in marketing, the way you approach upsell opportunities will depend on your customer. Customer data will uncover their pain points, highlighting which of your premium features they should know about. It will also uncover the best delivery format: simple and streamlined for busy users or full access for those who want to try it all first.

The best way to optimize your upselling technique is to zero in on a method and test it. Then you can continually tweak to ensure you’re always delivering the right message at the right time.

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8 Upselling Examples from B2B and B2C companies: Why They Work