The main difference between cross-selling and upselling is what you are offering. Upselling recommends a more advanced version of the same product, while cross-selling suggests a different product that complements the original one.
Upselling is about moving a customer to a higher-tier option. If someone is about to buy your basic software package, consider the professional plan that includes more features or capacity. The goal is to increase value by upgrading their intended purchase.
Cross-selling introduces a new product that supports or extends the original purchase. If someone is buying your CRM, and you suggest adding a conversation intelligence tool to improve coaching, that’s cross-selling. You are solving a related problem, not just enhancing the original solution.
Here’s a simple way to think about it:
- Upsell = a better version of the same product.
- Cross-sell = a complementary product that adds value.
Another key difference is timing. Upsells usually happen before the initial purchase is complete. Cross-sells can occur during the sales process or later in the customer lifecycle, especially when new needs are uncovered.
Both strategies can grow revenue, but the best results come when they are rooted in customer success. Reps should lead with value, not volume. G2 research reveals that 58% of pipeline stalls occur when reps fail to add value.
When the recommendation helps the buyer win, it’s also a win for your business.
What Is Upselling?
Upselling encourages customers to choose a more advanced or premium version of the product or service they are considering. The goal is to help the customer get more value, not just to increase the deal size.
For example, a sales rep speaks with a customer ready to buy a basic software package. During the conversation, the rep learns that the customer’s team plans to grow in the next few months. Instead of recommending the entry-level option, the rep suggests a plan with more users, added functionality, and onboarding support. That’s upselling. The customer gets a solution that fits their future needs, not just their current one.
When done well, upselling is consultative, not pushy. It’s based on understanding the customer’s goals and guiding them toward the best long-term fit. Upselling works when it feels helpful. If it improves outcomes for the customer, it improves outcomes for the business.
Today, the best sales teams use data and conversation intelligence to drive their upsell strategy.
What is Cross-Selling?
Cross-selling is recommending a related or complementary product that adds value to what the customer is already planning to buy. It is not about selling more for its own sake. It is about providing a more complete solution.
Let’s say a customer is about to purchase your CRM platform. If your rep learns that the sales team struggles with coaching consistency, they might suggest adding a conversation intelligence tool. That recommendation doesn’t replace the CRM. That is cross-selling.
Cross-selling works best when the rep understands the customer’s use case and long-term goals. It also requires trust. Customers are more likely to buy complementary solutions when they believe the rep solves a real problem, not just increases the order size.
This is where AI can make a big difference. Tools like Revenue.io identify patterns across millions of sales interactions and highlight opportunities to introduce helpful add-ons. These insights allow reps to act with context and confidence.
When cross-selling is done with care, customers feel supported, not sold to. And because the solution delivers more value, retention and expansion become easier over time.
How to Upsell and Cross-Sell Effectively
The most effective upselling and cross-selling strategies start with one principle: focus on value, not volume.
Reps shouldn’t push additional products or upgrades just to increase deal size. Instead, they should aim to make every recommendation solve a real problem or improve the customer’s long-term success. That’s how you earn trust and drive growth simultaneously.
Here are a few fundamentals for effective execution:
- Listen first, recommend second.
Every upsell or cross-sell should be based on your discovery. Reps who actively listen can uncover future goals, pain points, or use cases that the buyer has yet to fully articulate. - Time it right.
Upsells often work best during the decision-making process. Cross-sells may come later, once the customer has started using the product. Rushing either one can feel forced. - Position the benefit, not the price.
It’s not about a higher tier or a second product, but what that extra capability will help the customer achieve. Lead with outcomes. - Use data to guide the conversation.
Top-performing teams use AI and conversation intelligence to surface buying signals. Reps can confidently tailor their recommendations when those insights are real-time and contextual.
When you approach upselling and cross-selling with the customer’s success in mind, you don’t just close bigger deals. You build stronger, longer-term relationships.
Technology can make or break your upsell and cross-sell strategy. The right tools surface opportunities, guide reps in the moment, and ensure nothing gets missed across accounts and deal stages.
We asked Ryan Vaillancourt, VP of Sales at Revenue.io, how top sales teams can use AI to drive cross-sell and upsell success without losing trust.
“Upselling and cross-selling only work when they’re rooted in timing and trust. Data and AI help reps know when the moment is right—but reps still need to earn the right to recommend.”
The best sales teams don’t rely on memory or scattered notes. They use tools that help them act on the right insights at the right time, putting the customer first.
Here are a few categories to consider:
Conversation intelligence platforms help reps identify real-time buying signals during calls. These tools highlight when a customer asks about additional functionality, expresses a future need, or hints at scaling. This context is key for recommending the right solution at the right time.
Revenue intelligence systems track deal progress, surface gaps, and monitor key behaviors across the pipeline. They help managers and reps see where value can be added, whether that means a plan upgrade or an adjacent product.
This gives reps a real-time assistant that brings context and clarity. It boosts upsell and cross-sell readiness and ensures that each motion is grounded in data, not guesswork.
The best sales teams don’t rely on memory or scattered notes. They use tools that help them act on the right insights at the right time, putting the customer first.
Example Questions to Promote Cross-Sell Opportunities
Cross-sell conversations work best when they’re based on curiosity, not assumption. These questions help uncover unmet needs and open the door to complementary solutions:
- “How are you currently handling alongside this solution?”
- “Is your team using any other tools to support this part of the workflow?”
- “What challenges are you still facing after implementing ?”
- “Would it help if your worked more closely with ?”
- “Have your managers mentioned any gaps in visibility or coaching since rollout?”
- “Are there other teams or functions that could benefit from a similar solution?”
These questions are designed to surface opportunities without pushing. They show the rep is thinking holistically and looking to solve the bigger problem, not just sell more software.
Example Questions to Promote Upsell Opportunities
Upsell questions are about scaling impact and aligning to future needs. These examples help reps identify where a more advanced version of the product may be a better fit:
- “How do you see your team or process evolving in the next 6 to 12 months?”
- “Are there any features you’ve been curious about but haven’t tried yet?”
- “Do you anticipate needing more as your team grows?”
- “Would additional reporting or analytics help your leadership team make faster decisions?”
- “What does success look like six months from now—and can your current plan get you there?”
- “Has anything changed since you first chose this plan that might impact what you need?”
These questions uncover scale, complexity, or growth drivers that justify a smarter, more valuable product version.
Check out how revenue platforms like Ask Revenue are built into Revenue.io, and take this further. Ask Revenue allows reps to ask questions about any account, deal, or opportunity in plain language, like “What other products has this customer asked about?” or “Which deals are ready for an upsell?
