How to Improve Cross-Selling: Strategies For SaaS Businesses

How to Improve Cross-Selling: Strategies For SaaS Businesses cover

Learning how to improve cross-selling will let you tap into customer potential, provide additional value, and boost long-term retention.

It’s much easier to sell to existing customers than to win over strangers, but how exactly do you cross-sell to SaaS users?

This article answers your questions with proven cross-selling strategies and examples from top SaaS companies.


  • Cross-selling is a sales and marketing tactic that helps increase the average order value by selling additional or complementary products to current customers.
  • Effective cross-selling offers the following benefits:
  1. Adds more value for existing customers.
  2. Improves customer retention.
  3. Increases the customer lifetime value.
  4. Increases revenue through expansion.
  • Cross-selling and upselling are two different ways to increase expansion revenue. The former offers additional products or complementary items to the customer’s initial purchase, while upselling encourages customers to choose a more expensive version of the product they are already considering.

Strategies and best practices to effectively cross-sell SaaS customers:

  • Identify best cross-selling opportunities across the customer journey using path analysis.
  • Use customer data segmentation to identify your most profitable customer segments and trigger relevant cross-selling campaigns.
  • Set data-driven prompts to suggest relevant features.
  • Use contextual automated in-app messages to cross-sell to engaged users.
  • Use a personalized cross-selling approach with complementary products.
  • Leverage the signup flow to bundle relevant cross-sell offers.
  • Offer free trials or credits to current customers.
  • Start your cross-sell tactics at the acquisition stage.
  • Promote a new add-on with email marketing campaigns.

7 Examples of effective cross-selling techniques:

  1. Loom cross-sells stand-alone features using reverse trials.
  2. Zoom prompts users to try their web conferencing add-ons.
  3. CyberGhost VPN recommends relevant features during the signup process.
  4. InVision cross-sells its Freehand tool to remote teams.
  5. Skillshare suggests relevant add-ons contextually.
  6. Notion launched the Notion AI feature with a waitlist.
  7. TrustPulse prompts users to add Optinmonster to their purchase.
  • Metrics to track your cross-selling efforts: Account renewals, retention rate, and customer lifetime value.
  • Userpilot can help you create effective cross-sell strategies at different points in the customer journey by helping you track product usage, trigger cross-sell prompts, and gauge user experience with surveys. Book a demo to explore more.

What is cross-selling?

Cross-selling is a sales and marketing tactic used to sell additional products or services to existing customers to increase the average order value. It involves identifying products or services that complement or enhance the value of the customer’s purchase and prompting them to spend more.

Cross-selling aims to increase your product’s overall value and utility for the customer while also boosting your revenue.

Why implement a cross-selling strategy?

Cross-selling comes with multiple benefits for SaaS companies. Below are a few reasons every company should have it as part of their long-term growth strategy:

Add more value for existing customers

One of the primary reasons to implement a cross-selling strategy is to provide additional value to your existing customers.

By identifying their needs and preferences, you can offer add-ons that align with what they’re already using. This not only makes their current solutions more robust but also simplifies their experience and makes them enjoy your product more.

Improve customer retention

Think about it: will you easily leave a tool that always anticipates your needs and provides proactive solutions to solve them?

Probably not. The same thing happens to your users. Customer satisfaction generally increases when people can get more done with your tool. This enhanced efficiency boosts retention and loyalty.

Increase the customer lifetime value

Cross-selling directly impacts LTV by extending the duration of a customer’s relationship with your brand and increasing their overall spending.

Customers will want to invest time exploring the new features and add-ons they bought, so this will motivate them to keep renewing their accounts. Once they start seeing positive ROI from the complementary tools and features, it becomes an extra boost to keep subscribing, leading to high LTV.

Increase revenue through expansion

All the benefits we mentioned so far ultimately lead to increased revenue.

It’s worth noting also that cross-selling creates predictable revenue streams. As users commit to additional services, you can anticipate and project recurring revenue with a higher degree of confidence. This predictability is vital for financial planning and growth.

Additionally, cross-selling can lead to market expansion. When users discover the value in your cross-sold products, they may recommend them to others, further expanding your customer base and revenue potential.

Cross-selling vs upselling

While both cross-selling and upselling focus on increasing LTV and revenue expansion, there’s still a key difference between them.

Upselling encourages customers to upgrade or purchase a more expensive version of the same product. The goal is to convince customers to spend more by selling them on a premium or upgraded version.

For example, imagine you’re a project management tool offering a basic plan with essential features like task management and basic reporting for a standard monthly fee. Upselling is when you prompt customers to pay for your premium plan and access advanced project analytics, resource management tools, and priority support.

Bundling is another form of upselling. It involves offering a package of multiple products, usually at a discounted price, and convincing customers to pay more than they initially planned.

On the other hand, cross-selling focuses on expanding the customer’s purchase horizontally, introducing them to a broader range of features that add extra value to the initial product.

The difference between cross-selling and upselling.
The difference between cross-selling and upselling.

Cross-selling strategies and best practices for SaaS

Now that you’ve seen the benefits, here are proven strategies to create effective cross-selling for your SaaS:

Identify best cross-selling opportunities across the user journey using path analysis

Conduct a thorough path analysis to understand how users interact with your product and pinpoint moments where additional features or complementary products can add value to users.

After launching successful cross-selling and upselling, use the same path analysis to track how users journeyed to that conversation point. Based on the data generated, identify opportunities to shorten the path and convert more users.

Path Analysis will be released in Userpilot in Q4 2023.
Path Analysis will be released in Userpilot in Q4 2023.

Use customer data segmentation to identify relevant cross-selling opportunities

By dividing your customer base into segments based on shared characteristics, such as industry, company size, or usage patterns, you can gain valuable insights into their needs and preferences. This segmentation would allow you to trigger contextual cross-sell prompts and convert more users.

In addition, you can segment customers that have adopted your add-ons. Track product usage for these user segments. Note their usage patterns and use that insight to identify specific user segments that would benefit from more value and cross-sell to them.

Customer data segmentation with Userpilot.
Customer data segmentation with Userpilot.

Set data-driven prompts to suggest relevant features

Use software like Userpilot to automatically trigger contextual upgrade prompts based on the data you collected about your users.

You can send these prompts to specific user segments that you consider ripe for your cross-sells or make them event-based. A good example of when to trigger an event-based prompt is when a user reaches a usage threshold. This shows they’re well-engaged with your tool and probably ready to explore more.

Creating event-based experiences with Userpilot.

Use contextual automated in-app messages for better results

In addition to data-driven prompts, you can also implement contextual in-app messages that appear at the right time within the user interface. These messages should provide context-specific cross-selling suggestions, ensuring they are not intrusive but enhance the user experience.

You’ll find that it works better than relying solely on a sales representative or customer support team to reach out to users. Since the prompt is contextual and relevant to what the user is doing at the moment, the chances of conversion are high.

This tooltip was created with Userpilot solely to showcase contextual in-app messages.

Use a personalized cross-selling approach with complementary items

This strategy is common with e-commerce companies, especially ones that use a free shipping threshold to drive more sales. Have you tried buying something on Amazon and got recommendations of things that other people buy along with the product you chose?

That’s personalized cross-selling at work. You can apply the same logic to your SaaS. Analyze customer profiles, behavior, and usage patterns to understand their preferences, then recommend relevant products or features that enhance their current experience.

Leverage the signup flow to bundle relevant cross-sell offers

New customers come to your tool with heightened interest and enthusiasm. They’re eager to explore your platform and see how it helps solve their problems.

Seize this opportunity to cross-sell them with bundle offers.

Design a seamless signup experience that introduces users to relevant cross-selling options without causing friction. Clearly communicate the value of your bundled offers and discounts during the signup process, ensuring users understand how these additions enhance their overall experience.

Offer free trials or credits to existing customers

Free trials or credits provide existing customers with a hands-on experience of the complementary features or products you’re trying to cross-sell.

This strategy allows users to test the value of the offering firsthand, reducing hesitation and increasing the likelihood of adoption.

Tailor the free trials or credits based on the customer’s current usage and needs. Clearly communicate the duration of the trial and the benefits of the cross-sell offering.

It also helps to monitor customer engagement during the trial period to gauge interest and potential conversion. This enables you to identify and segment the users most likely to convert after the trial period.

Free credits offer from SurferSeo.

Start cross-selling during the acquisition stage

Collaborate with the sales team to offer special discounts for bundles available at signup only.

Realizing the discounts are timebound will make new customers eager to jump on it. This strategy will contribute to long-term retention because users will quickly explore your tool’s functionalities and start seeing ROI immediately.

Promote a new add-on with email marketing campaigns

In-app campaigns are effective because users see them when engaged with your tool. However, don’t limit yourself to just one channel.

Utilize targeted email marketing campaigns to promote new add-ons or features to your existing customer base. Make your emails compelling and ensure to highlight the benefits of the new offering. Always end with a CTA that encourages customers to explore the additional value your add-on brings.

Oura’s email marketing campaign.

7 Examples of effective cross-selling techniques

You’ve learned different cross-selling strategies to implement for your SaaS. It’s time to see them in action.

Below are seven cross-selling examples from top companies to inspire you:

1. Loom cross-sells stand-alone features using reverse trials

Remember the strategy about letting users try your add-ons before they buy?

Loom implements it perfectly. Users are granted limited access to its new feature so they can see how it works before prompting them to upgrade.

Notice how Loom doesn’t let users reach the trial end before asking them to upgrade. By sending the prompt in time, users are reminded that they have just one free usage left. This timely reminder helps users make a final decision about upgrading.

Loom’s upgrade modal.

2. Zoom prompts users to try their web conferencing add-ons

Rather than wait for later in the user journey, Zoom uses its sign-up process to show users different add-ons.

This encourages new users to pay more and unlock a better Zoom experience. And even if they don’t upgrade immediately, at least users have seen what’s available and can later visit that page when they need it.

Zoom's add-on plans.
Zoom’s add-on plans.

3. CyberGhost VPN recommends relevant features during the signup process

Similar to Zoom, CyberGhost VPN uses the signup screen to showcase its add-ons.

To address buying objections and increase the customer lifetime value, the platform prompts users to pay two years upfront for the add-ons and save 78% and 50%, respectively. Adding the recommended tag on the first feature was also a good move to encourage purchase—most new users are in doubt when making a purchase, so the tag helps them choose.

Cross-selling example from CyberGhost.
Cross-selling example from CyberGhost.

4. InVision cross-sells its Freehand tool to remote teams

InVision is a good example of how studying user behavior helps you unlock opportunities for account expansion.

The company noticed how remote teams use their platform and prompted this user segment to try its Freehand tool and improve remote collaboration:

InVision’s cross-selling example.

5. Skillshare suggests relevant add-ons contextually

Skillshare is a learning community with thousands of courses across different topics.

Unless you have a particular course or creator in mind, it’s difficult for even experienced users to find exactly what they want.

To make it easier for customers and to generate more revenue, Skillshare leverages user information to suggest relevant courses:

Skillshare’s intelligent course recommendations.

6. Notion launched the Notion AI feature with a waitlist

When its add-on feature was ready, Notion paired email and in-app campaigns to draw user attention and drive more engagement.

Interested users were required to join the waitlist and wait for their turn to explore the feature. If you were curious about the feature and wondering if it’s worth the wait, Notion had a 1-minute demo video to answer your questions:

Introducing Notion’s cross-selling process.

When you join the waitlist, you’ll get an email confirmation and a pop-up like the one below. (These steps weren’t necessary, but Notion created them to gamify the wait and maintain user interest).

Loom didn’t stop there. Users were shown their positions on the waitlist to create a sense of scarcity. The screenshot below shows this account was number 244,765 on the waitlist. Seeing this number is enough motivation to share your unique link with the people in your network and move further up.

Loom’s modal encouraging users to share the waitlist link.

After following the steps above, users got free credits when the feature was launched. Once the free credits are exhausted, you’ll have to pay to get more.

Notion AI checkout page.

7. TrustPulse prompts users to add Optinmonster to their purchase

This final example shows the importance of cross-selling a different platform that will add more value to your users and encourage continuous engagement.

TrustPulse cross-sells Optinmonster on the checkout page, prompting users to pay more and achieve better results. Notice how the platform gives a discount to sweeten the deal:

TrustPulse’s post-purchase cross-selling technique.

It’s worth noting that TrustPulse is an Optinmonster company, but you can apply the same tactic with a different company, provided the tool will make your users’ lives better.

Metrics to track your cross-selling efforts

It’s not enough to deploy cross-selling strategies. You also have to regularly track your results and adjust accordingly.

Here are three key metrics you should be tracking:

  • Renewals: Measuring the percentage of customers who continue their subscriptions after being cross-sold lets you assess the effectiveness of your cross-selling strategies. You can track sub-metrics like renewal rate by product, renewal rate by customer segment, and time to renew to get comprehensive insights.
  • Retention rate: A high retention rate indicates that customers are not only acquiring additional offerings but also staying engaged and satisfied over an extended period. It reflects the effectiveness of cross-selling in building long-term customer relationships.
  • Lifetime value: Evaluate the additional value contributed by cross-sold add-ons to the overall lifetime value of customers. By tracking this metric, you can understand if your cross-selling efforts are paying off. This will let you decide how much resources to invest in future campaigns.

How Userpilot can help you get started with your cross-selling strategy for existing customers

Userpilot is a product adoption and growth tool that helps SaaS companies like yours to cross-sell effectively.

Here’s how our platform can help:

  • Feature tagging: Use feature tagging to track feature usage and see which aspects of your tool are most popular among active users. Based on the insights from this, you can identify cross-selling opportunities to exploit.
  • In-app flows: From tooltips to modals, Userpilot has different UI elements you can combine to create in-app flows and trigger contextual prompts. You can use flows to educate users on the value of your add-ons, remind them to upgrade, or direct them on how to pay.
  • Surveys: In-app surveys let you collect data directly from users to understand their experiences and pain points. By doing this, you will find critical points in the user journey where cross-selling will work. And that aside, based on user responses to your surveys, you can trigger a cross-sell to solve their problems. For instance, if a user replies that they need additional features they didn’t know existed on a premium plan, that’s your opportunity to prompt account expansion. When it comes to surveys, Userpilot lets you build different kinds of in-app surveys, from quick CSAT surveys to more in-depth qualitative questions. Our platform also lets you analyze and act on feedback in real time.


Conversion happens when users feel like you’re genuinely helping them, not just trying to promote your product.

To make this happen, you need to personalize your campaigns to their needs and preferences. Don’t showcase add-ons you know aren’t suitable for the user’s JTBD.

One way to be effective with this is to regularly track user behavior and see what they interact with. That way, you can tell their pain points and needs. Surveys also come in handy because they let you hear directly from the horse’s mouth.

Userpilot can help with these and more. Book a demo with our team now to discuss your needs and improve your cross-selling efforts.

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