Upselling vs. Cross-selling: How Customer Success Managers Can Use Both to Drive Growth

Upselling and cross-selling are everywhere—whether it's an extra shot of espresso in your coffee or a bundle deal on software. They are two of the most effective ways to expand customer relationships and drive revenue growth, but they’re often misunderstood—or worse, used interchangeably. 

Many Customer Success Managers (CSMs) struggle with knowing when to upsell versus when to cross-sell, leading to missed opportunities or offers that don’t quite land with customers.

Push an upsell too soon, and it might come across as unnecessary. Offer a cross-sell without clear relevance, and customers may feel like they’re being sold something they don’t need. Finding the right balance requires careful timing, data-driven insights, and a customer-first approach.

This blog breaks down the differences between upselling and cross-selling, shares best practices, and explores how CSMs can execute these strategies effectively—without making customers feel pressured.

What is upselling?

Upselling encourages customers to move to a higher-tier plan or add premium features to their current package. The goal is to enhance their experience by giving them access to more advanced capabilities that better meet their needs.

For example, a customer using the basic version of a SaaS tool may hit usage limits or require more automation. A well-timed upsell to a premium plan, where they gain access to advanced features like AI-powered analytics or automated workflows, can help them scale efficiently.

What is cross-selling?

Cross-selling involves offering complementary products or services that enhance a customer’s experience. Instead of upgrading their current plan, customers are introduced to features or add-ons that integrate with what they already use.

A good example is a company using a CRM being offered an integrated email marketing tool. The CRM helps manage customer relationships, while the email marketing tool enables personalized communication, making the overall solution more powerful.

Cross-selling works best when the additional product solves a problem the customer is already facing. If positioned correctly, it helps customers unlock more value from their existing investment, leading to greater satisfaction and long-term retention.

Both upselling and cross-selling are valuable, but they require a thoughtful, customer-first approach. If they’re forced or mistimed, they can have the opposite effect—leading to disengagement or even churn.

Key differences between upselling and cross-selling

‍

While both upselling and cross-selling aim to increase customer value and revenue, they work in different ways and should be used in different scenarios. Understanding these differences helps ensure that recommendations feel relevant and beneficial rather than forced or unnecessary.

Goal: Expanding within vs. beyond the current product

Upselling encourages customers to upgrade within the same product or service they are already using. The goal is to move them to a higher-tier plan or provide access to premium features that enhance their current experience. 

This works well when customers have outgrown their existing setup or need additional functionality to achieve better results.

Cross-selling, on the other hand, involves offering complementary products or services that integrate with what the customer is already using. 

Rather than expanding the features of their current product, cross-selling introduces tools that provide added value and create a more complete solution. A good cross-sell doesn’t replace or compete with the existing product—it enhances it.

Impact: Strengthening vs. Expanding Usage

The impact of upselling is a deeper engagement with the current product. Customers who upgrade tend to use the platform more extensively, take advantage of premium features, and rely more heavily on the service. 

This can lead to stronger retention because customers feel they are getting everything they need from one solution.

Cross-selling, however, broadens the ecosystem of tools a customer interacts with. When a complementary feature or product is introduced, it increases overall product adoption and makes the software more valuable across different use cases. 

This kind of expansion helps embed the product more deeply into the customer’s operations, reducing the likelihood of churn since multiple tools are now connected.

Best suited for: Different customer needs

Upselling is best suited for customers who have growing needs and are experiencing limitations in their current plan. If a customer frequently reaches their plan’s limits, engages heavily with the product, or requests features that are only available in higher tiers, an upsell conversation makes sense.

Cross-selling is a better fit for customers who could benefit from an additional product but may not need an upgrade. If a customer is managing well with their current plan but is looking for ways to enhance their workflow, cross-selling can introduce features that make their experience more efficient.

How to approach them differently

The way these strategies are introduced also differs. Upselling should be framed as helping customers scale—they are already seeing value, and an upgrade will allow them to unlock even more functionality. It should be presented as a natural next step rather than an additional cost.

Cross-selling should be positioned as filling a gap—showing customers how an add-on or complementary tool can solve a problem they are already facing. Instead of making it feel like a separate purchase, it should be integrated into their workflow in a way that highlights its immediate usefulness.

Both upselling and cross-selling can drive meaningful growth for customers and businesses, but only when done thoughtfully. The next step is knowing when to apply each strategy to ensure it delivers real value.

When to use upselling

Upselling is most effective when a customer is approaching the limits of their current plan or when an upgrade would directly solve a pain point they’re facing. A good upsell feels like a natural next step rather than an unnecessary expense.

Here are some key moments when upselling makes sense:

When a customer is reaching usage limits 

If a customer is frequently maxing out their current plan, such as running out of storage, hitting API limits, or needing more advanced features, it’s a strong indicator that an upgrade could provide real value.

When they’re looking for more efficiency

If a customer is manually handling processes that could be automated, an upsell to a plan with AI-driven automation or advanced integrations could save them time and effort.

When their business is scaling

As companies grow, their needs evolve. If a customer has expanded their team or increased their customer base, they may benefit from a higher-tier plan that supports additional users or offers enhanced reporting.

When they’ve had a positive experience with your product 

Customers who actively engage with your product and see its value are more likely to be open to an upgrade. Using customer health scores can help identify accounts that are in a good position for an upsell.

The key to effective upselling is timing and relevance. If a customer isn’t yet seeing the full value of their current plan, pushing an upgrade too soon can feel premature. Instead, focus on understanding their goals and highlighting how an upgrade aligns with them.

When to use cross-selling

Cross-selling works best when customers have an unmet need that a complementary product or feature can solve. Unlike upselling, which enhances their existing plan, cross-selling introduces new tools that integrate with what they already use.

Here are some situations where cross-selling is a strong strategy:

When a customer has a specific pain point that another feature solves

If a customer struggles with reporting, offering them an advanced analytics tool can help them gain deeper insights. If they rely on manual email follow-ups, an automated email sequence feature could be a great fit.

When they’re already engaged with your core product 

Customers who actively use and see value in your main product are more likely to be receptive to add-ons or integrations. If they’re only using a fraction of what’s available, introducing new tools can help them unlock even more value.

When they’re asking for a solution you already offer

Sometimes, customers are looking for features they don’t realize your product already provides. If a customer inquires about a need—like tracking customer sentiment—introducing a built-in sentiment analysis tool can be an easy win.

When other teams in their company could benefit from an additional product

If a company’s Customer Success team is using your platform, but their sales or support teams aren’t, cross-selling relevant features to other departments can help deepen adoption across the organization.

Successful cross-selling isn’t about pushing extra products—it’s about connecting customers with the tools that make their experience more seamless. The best opportunities come from truly understanding customer needs and offering solutions that fit naturally into their workflow.

Best practices for upselling and cross-selling

Upselling and cross-selling aren’t about offering everything to everyone. Success comes from knowing when and how to make the right recommendation.

1. Identify the right opportunities

Not every customer is ready for an upsell or cross-sell. The best opportunities come from analyzing customer engagement and product usage.

• Customer health scores can highlight accounts that would benefit from additional features.
• Usage data can reveal customers who are hitting their current plan’s limits and may need an upgrade.
• AI-driven customer sentiment tracking in a platform like Velaris can surface insights into when a customer might be open to an expansion conversation.

2. Align recommendations with customer goals

Instead of pushing features, position upsells and cross-sells as solutions to specific pain points.

• If a customer struggles with reporting, suggesting an advanced analytics add-on makes sense.
• If a customer frequently engages with support for manual processes, introducing automation tools can provide a clear benefit.

3. Use data-driven insights to personalize offers

A generic upsell or cross-sell rarely works. Tracking customer support interactions and product engagement can reveal exactly what a customer needs.

• AI-powered customer sentiment analysis helps identify what sort of offer a customer may be receptive to at a given time. 
• Success plans within a software like Velaris can map out the customer’s journey, ensuring any upsell or cross-sell aligns with their long-term goals.

4. Make it easy for customers to say yes

• Offering free trials or discounted upgrades allows customers to experience the benefits before committing.
• Providing clear ROI insights through customer success playbooks helps justify the investment.

5. Automate outreach without losing personalization

• Automated email sequences can introduce relevant upsell and cross-sell opportunities based on customer behavior.
• Messaging should still be tailored to each customer’s history and needs to keep interactions meaningful.

Conclusion

Upselling and cross-selling, when done thoughtfully, help both customers and businesses. The key is to introduce these opportunities at the right time, align them with customer goals, and ensure they feel like natural progressions rather than sales pushes.

Tracking customer health scores, monitoring engagement, and automating outreach can make upselling and cross-selling more effective and scalable. This is where a platform like Velaris can help—by unifying customer data, surfacing insights, and automating key touchpoints, CSMs can ensure they’re identifying and acting on the right opportunities without adding more to their workload.

If you're looking to make upselling and cross-selling more strategic and efficient, book a demo today to see how Velaris can support your team.