How to Use Data-Driven Upselling to Drive Expansion Revenue in Customer Success

Upselling isn’t easy, especially for Customer Success Managers (CSMs). You want to help your customers succeed, but pushing an upgrade at the wrong time can make the conversation feel awkward or transactional. 

Even when you believe an upsell would add value, it’s tough to know when a customer is actually ready – or whether they’ll see it as just another sales pitch. The real challenge? Most CSMs don’t have the data they need to make these conversations feel natural. 

Without clear insights into product usage, engagement trends and customer sentiment, upselling often becomes a guessing game. That’s where a data-driven approach changes everything. 

By leveraging the right metrics, you can identify when an upsell makes sense, personalize your recommendations and ensure customers see expansions as a logical next step. 

In this blog, we’ll explore how you can use data to make upselling more effective, timely, and customer-centric.

The foundation of data-driven upselling

Upselling works best when it’s based on real customer needs – not assumptions. Without data, CSMs often rely on gut feeling, which can lead to poorly timed or misaligned recommendations. 

The right data, however, helps you understand when a customer is ready for an expansion, what they actually need, and how to position it as a logical next step.

To make upselling feel like a natural part of the customer journey, CSMs need to look at specific data points that signal when a customer is open to an upgrade. 

These insights can help you move beyond generic sales pitches, and instead frame upsells in a way that aligns with the customer’s current experience and future goals. Here are the key types of data that can make your upsell efforts more precise and effective.

Types of data to leverage

1. Product usage metrics

When customers are consistently using core features or regularly hitting usage limits, it’s often a sign they’re ready for additional functionality. In contrast, low or inconsistent usage may indicate that they need more support or engagement before an upsell is appropriate.

2. Customer health scores

A strong health score often indicates a satisfied customer who is more likely to expand, while a declining score suggests they need support before discussing an upgrade.

3. Engagement analytics

Tracking logins, feature adoption and in-app activity can highlight customers who are getting value from the product and might be open to exploring more.

4. Sentiment analysis

Emails, support tickets and survey responses can reveal whether a customer is excited about your product (a good upsell opportunity) or frustrated (a sign they need troubleshooting instead).

5. Renewal and expansion history

Looking at past upsell trends can help predict which customers are likely to expand based on similar usage patterns.

How to collect and analyze this data

To apply a data-driven approach effectively, CSMs need to start by unifying data from sales, support, product and marketing teams. Without this, it’s hard to see the full picture of a customer’s needs. 

Once data is centralized, AI can help detect upsell signals – like increased feature usage or positive sentiment that might otherwise go unnoticed.

It’s also important to track behavior trends over time, not just isolated actions. This helps you anticipate needs before the customer brings them up. 

You can fix this by unifying data across teams and automatically flagging expansion opportunities with a Customer Success platform like Velaris. Next, let’s look at how to identify the right moments for an upsell to ensure your recommendations feel natural, not forced.

Positioning upsells as Customer Success, not sales

Even when the data clearly points to an upsell opportunity, how you approach the conversation matters. If it feels like a pitch, customers may tune out – even if the solution would genuinely help them. 

The key is to frame upsells as part of the customer’s success path, not a sales goal. Here are a few practical ways to do that:

1. Tie upsells to specific goals or pain points

Start by showing how the upsell directly supports what the customer is trying to achieve. If they’re scaling their team or automating more workflows, focus on how the upgrade helps with that – not just what it includes.

2. Personalize the conversation with data

Use customer data to make the upsell relevant. 

For example: “We noticed your team is using [Feature X] heavily. Many teams in a similar stage have found [Feature Y] helps them scale more efficiently.”

Or

“Your usage has increased by 40% over the past six months. Moving to [Plan Z] could help reduce performance issues and support future growth.”

3. Share relevant customer stories

Customers trust real examples. If another company in a similar industry or use case benefited from the upgrade, share that story. It makes the upsell feel more relatable and less theoretical.

4. Take a consultative approach

Position yourself as a partner, not a seller. Ask questions, listen and offer guidance based on what you’re seeing in the data.

5. Time outreach based on behavior and sentiment

Use automated, trigger-based email sequences to surface upsells at the right time. AI-powered sentiment analysis can also help you identify when a customer is expressing a need an upgrade could address.

You can streamline this kind of targeted outreach with tools like Velaris, which lets you set up automated email flows based on behavior or sentiment.

Next, let’s look at a few frameworks and tools you can use to support a more consistent, repeatable approach to data-driven upselling.

Tools and frameworks for data-driven upselling

Having the right mindset and data is important – but so is having a consistent and repeatable approach. Frameworks help CSMs apply the same principles across different accounts, while tools make it easier to act on insights quickly. 

Here are a few practical approaches that can support smarter upselling.

1. The customer health score model

This model combines key indicators like product usage, engagement levels and support interactions to give you a real-time view of how a customer is doing. 

A strong health score can point to accounts that are ready for an upsell, while a declining score may signal a need to re-engage before making any recommendations.

2. The success milestone framework

Every customer has moments in their journey where they’re more open to new value – like after onboarding, hitting a key adoption milestone or launching a new initiative internally. 

Mapping these out helps you time the upsell around what matters to the customer and not your internal calendar.

3. The engagement-based approach

This framework focuses on identifying and acting during periods of high engagement. If a customer is actively using the product, joining webinars or giving strong NPS feedback, they’re more likely to see the value in expanding their plan.

4. Technology to support your process

Customer Success platforms that integrate data across usage, sentiment and health scoring will help you stay focused on the right accounts. 

When paired with AI tools, these platforms can also help surface potential upsell opportunities and automate outreach based on real customer behavior. 

For example, Velaris allows CSMs to build success plans, track key milestones and run targeted upsell campaigns using AI-generated insights – all within a single workflow.

Next, let’s look at how to measure the impact of your upsell efforts and ensure they’re contributing to long-term customer growth.

Measuring success: Tracking the impact of data-driven upselling

Upselling isn’t just about closing the deal – it’s about driving long-term value for both the customer and your business. To understand whether your approach is working, you need to look at the right metrics and use that data to refine your strategy over time.

Here are a few key metrics that can help you measure the short and long-term impact of your upsell efforts:

1. Expansion revenue

This tells you how much revenue is being generated through upsells while giving you a clear view of the financial return on your efforts.

2. Customer lifetime value (CLV)

Successful upselling should increase the total value a customer brings over time. Tracking CLV helps you connect upsell efforts to overall growth.

3. Upsell conversion rate

This measures how many of your upsell opportunities actually turn into results, helping you gauge the effectiveness of your messaging and timing.

4. Customer retention and churn rates 

Done well, upselling should strengthen retention. If churn increases after an upsell, it’s worth revisiting how those conversations are being handled.

5. Feature adoption post-upsell

It’s not just about selling more – it’s about ensuring customers use and find value in what they’ve added.

Regularly reviewing these metrics, alongside direct customer feedback, helps you learn what’s working and where to improve. With Velaris, you can track all of this in real time through dashboards and reporting, making it easier to adjust your approach as you go.

Next, we’ll wrap up with a few thoughts on how to make upselling feel like a natural part of helping customers succeed.

Conclusion

Upselling doesn’t have to feel like a separate task from Customer Success. When it’s backed by data, framed around customer goals and delivered at the right time, it becomes a natural part of helping customers get more value from your product.

The key is having the right information, a repeatable process and tools that make it easy to act on insights. Whether it’s tracking feature usage, identifying key milestones or automating timely outreach, a data-driven approach helps you focus on the accounts where an upsell actually makes sense.

If your current process makes it hard to spot opportunities or have the right conversations at the right time, Velaris can help. It brings your data together, highlights upsell signals and gives you tools to engage customers in a way that feels relevant – not forced.

If you're looking to make upselling more timely and customer-focused, book a demo today and see how Velaris can support that shift.