We’ve all been there-you’re coming to the end of the checkout process on a website you’ve probably purchased from before, and a section comes into view with a message ‘have you forgotten this?’ or ‘customers also purchased x y or z’. This is a tried and tested cross-selling strategy - it encourages or persuades customers to buy additional, sometimes ‘’add-on’ purchases at the time of the transaction.

In this article you’ll learn:

Intro to cross-selling and upselling

Upselling differs slightly in that potential customers might be encouraged to buy a more expensive, higher spec, or ‘premium’ version of a product when they probably intended to sign up for the standard version. So - they both have the same goal, i.e. to increase sales, but have slightly different ways of going about it.

In terms of the structure of your organization, cross and upselling may fall under the remit of customer marketing, sales, demand gen, customer success, or a hybrid of these.

Both cross-selling and upselling are hinged around a customer’s confidence in your brand and product, but also based on offering the right product at the right time, to the right customer - in a way that doesn’t come across as ‘salesy’ and tacky, but in a way that enriches the overall customer experience.

Examples from Asos & Spotify

Screenshot from asos website suggesting complementary items to the customer before purchase.

Let’s take a look at a couple of examples. ASOS, an e-commerce fashion giant, suggests complimentary items ranging from clothing to cosmetics each time a user views a product - even before anything is added to the shopping basket, encouraging the user to consider not just one piece but the entire outfit - a great example of cross-selling.

Spotify includes clever in-app nudges to upsell to customers on freemium plans. If you get too skip-happy while using the mobile app, it will remind you that basic users are confined to six skips each hour.

While this can get frustrating after a while, prompting users to either abandon or upgrade, the messaging remains soft, and there are playlists available curated by Spotify that have unlimited skips even as a free member. Periodically, messages will also pop up reminding users of the benefits of a premium subscription.

This is the case with products such as Mediatoolkit - once a user has reached the limit of their queries or mentions, they’re prompted to upgrade, and depending on the persona or profile involved, this could be with or without a discount.

Mediatoolkit places a limit on their services triggering a prompt for the customer to upgrade to premium.

Here’s another example from CoSchedule - here we have a time-specific offer that coincides with a national holiday, offering an upsell to a pro membership, drawing the eye to additional features that may be of benefit to the user.

Co-schedule time specific offer fro updating to premium to upsell.

So why do these cross-sell and up-sell methods work? In the case of ASOS, it successfully targets the user’s aesthetic, by showcasing literally thousands of enviable outfit combinations that the customer can recreate for themselves - by highlighting what is relevant, on-trend, and complimentary.

In the case of Spotify, the freemium user is treated to a taste of what the product is like for a premium subscriber, and rather than this feeling like a paywall, most of the time it feels like a teaser that becomes the hook, encouraging the user to make the jump to one of their paid memberships.

Two takeaways, then: give users an authentic glimpse into a paid subscription, and showcase relevant, personalized options that spark their interest.

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Best practices

Whatever your involvement with cross and up-selling, shifting strategy to make it a more enriching experience for a user is super important. In conversations with customer markers and product marketers, we came across several recurring issues which helped to form these best practices. Let’s take a look.

Who and when

Timing is tricky and not as easy as it sounds. Trying to cross-sell (or up-sell) to a customer that has a lot of support tickets or that has a low net promoter score isn’t a good idea.

There are a few options: the point of purchase when they’re already in the buying stage, a moment in-app in which a need arises, or when a moment of difficulty is identified in customer support or customer success.

Segmentation will help identify the who - and if it’s an existing customer you should already know a lot about them. Harness the data you gather from customers at every stage of their journey - purchase histories, number of tickets, and so on, can help to form a series of blueprints of people who demonstrate particular behaviors at particular times.

Collaboration between product marketing, customer marketing, and customer success is vital, and product marketing can help with automation-based segmentation. This is also where your customer journey map comes into play - it will help identify when the best times may be for a given segment.

For example, if onboarding data looks good and engagement is steady, it might be a good time to follow up with upgrade nudges. Automation can come into play, depending on your organization’s capabilities - AI tools can automatically contact customers who display interest in certain products.


Igor Kranjcec, Head of Marketing at Mediatoolkit, encourages caution when it comes to sales: he says ‘don’t try to sell something just to meet your targets; I know the sales team has targets, I know they need to push the products, but in the long run it results in a down-sell or even churn because you sold them something that they didn’t use in the end.’

He also adds that further training for sales and customer success is so significant as they can recognize opportunities for up-selling on a case-by-case basis - they will know customers very personally and can use this to their advantage.

We’ve already uncovered another two approaches: let users discover features through a freemium product, as well as personalizing based on knowledge and data. Here are some more:

  • let users discover or experience a taster of the premium version
  • personalize your recommendations based on your knowledge of the user and or data
  • think about problems and solutions
  • leverage newsletters, emails, knowledge-based content and in-app comminications
  • experiment with various prompts

It’s key to think about problems your customers might be facing along the customer journey and align them with your product or its features. If you have a thorough understanding of these issues, you or your teams will have a range of solutions at your disposal. Listen carefully to your customers to seek out their unaddressed needs.

In a B2B and B2C setting, newsletters, emails, and educational content can also be targeted at different segments -  highlighting features that may be appropriate to the industry or needs of a given customer. These can also be delivered in-app, too, and give pointers on how it might enhance their experience and make their lives that little bit easier.

Different prompts can also be experimented with - you might choose to display a message when a user clicks an option that is limited to higher-level plans or products, which can guide customers to the realization that they do actually need these features if they’re clicking on them enough.

Be cautious, though, as too many limitations can frustrate rather than encourage. Another in-app or in-program tactic is to display current personalization and feature options next to upgraded features - interacting with these can give a preview of the possibilities, but limit any further interactions with that function. This can entice the user to want to find out more about the potential benefits of an upgrade.

Countdown features are also often useful to add - they can commonly be seen in Google Drive, for example. They are not too ‘in the face’, but serve as an ongoing reminder that there are limits to their current account status or subscription type, way ahead of the user reaching the point where they hit that limit and work out what to do next.

If you work with a SaaS product, you may have limits on the number of users, storage space, and so on - a visual reminder of these can drive home the message that a higher-level account would free them from any restrictions.

image of google drives outline for storage space used.

A great example of this is Slack’s limit on messages, which means that often over time, a user’s message history will disappear as their team surpasses its threshold.

It’s worth pointing out here that some companies may have issues with disparate sets of data when approaching cross-selling or upselling, especially if you’re using multiple tools - there is sometimes the problem that these datasets simply don’t match up and talk to each other.

This can have serious consequences and muddies the waters - not knowing which users have access to which products, attended an event or webinar, or other significant variables can quite simply stop any cross-selling opportunities in their tracks.

One possible course of action would be to proceed anyway, sending notifications or emails with campaigns regardless - but this will more than likely be a stab in the dark, potentially leaving some customers questioning why they got the message in the first place when they’ve already purchased a particular product. It’s a missed opportunity for data-informed decisions.

A way around this is to find a tool that bridges these data gaps, something like Segment for example, to unify all the crucial information you need to target the right users. The only downside of this is that there may be quite a vast backlog of data work to get through to reap the benefits, but the outcomes are more than worthwhile.

Anyone that touches customer data ideally should do their part to keep it up to date - that way it should always be relevant and gives an instant snapshot of where a user or account is at.

The bottom line is - existing customers are much easier to sell to. You’re 60-70% more likely to sell to an existing customer,  and the mantra to remember is the right customer at the right time, and what that looks like will be slightly different for everyone.

For your organization it benefits profitability, discourages churn, and promotes innovation - for your customer, upselling and cross-selling should increase their overall satisfaction, be convenient and address their pain points.


If you work in the B2B or SaaS spaces you may have renewals processes as part of your customer lifecycle, whether in the form of a subscription, license, or membership - it’s a crucial stage of the retention process, and if things have been rocky in terms of onboarding or engagement, this could be the point at which some customers go elsewhere, especially if they aren’t seeing the value in your offering and can find a viable alternative affordably.

Most businesses will have a dedicated sales team that oversees the process, but customer marketing can have some influence over renewals to ensure that customers continue that relationship. If you find yourself with any sway when it comes to processes, here are our suggestions.

If you haven’t done so already, a good place to begin is by standardizing your renewals process. The steps involved will vary depending on your organization, but they might include:

  • Automated reminders
  • Automated billing
  • Notifications of service agreements and pricing changes
  • Upgrade invitations

Here are our top nuggets of advice to ensure that renewals aren’t an afterthought.

  1. Retention is an ongoing process, not just before renewal.

If you suddenly start pulling out all the stops a while before a customer is up for renewal, they might just get aggravated that this information or customer service wasn’t available to them previously.

The reality is that content explaining product features, nurture campaigns, invitations to events and so on should have happened much, much earlier.

2. Make it as easy as possible

Seamless, secure, transparent, and easy peasy - as with any transaction, make it simple. Put yourself in the customer’s shoes, or even better, ask for feedback - what would make payments easier?

3. There’s no ‘i’ in renewals

Anyone that has a hand in the customer journey or is in a customer-facing role has a part to play, and customer marketers guide that tone. Evaluate your comms across the board, and meet with all teams to ensure that customers are on the path to adoption and retention early on.

4. Heed the warning signs

It’s worth segmenting or grouping renewers so you can identify patterns in those who might drop off, and also first-time renewers vs repeat renewers.

It can be helpful to have a look through user data early on to keep an eye on how certain customers or segments are using the product and what for so you can plan strategy accordingly, alongside regular checks of NPS (Net Promoter Score) to avoid the renewal slippery slope.