Upselling Strategies & Techniques for B2B Sales Teams

What is upselling?

Upselling is the practice of encouraging customers to purchase a more premium version of your product or add-ons that enhance their original purchase. At its core, it’s all about offering more value to existing customers while increasing the overall value of each account. 

In 2025, upselling has become even more important for sales teams — all of which face difficult economic realities, growing competition, and increasing customer expectations. Since it’s easier and cheaper to sell to existing customers than acquire new ones, it comes as no surprise that upselling can boost revenue by at least 10% to 30%.

Upselling vs. cross-selling: What’s the difference?

While upselling and cross-selling are both mechanisms sales teams can employ to drive more revenue, there are important distinctions between the two.

Upselling involves encouraging a customer to buy a more expensive or upgraded version of a product they’re already using or considering. For example, if a customer has a lower-tier subscription to a marketing automation platform, a sales rep might encourage them to upgrade to a premium subscription to unlock advanced features. 

Cross-selling, on the other hand, involves recommending related or complementary products that go with what a customer is buying. For example, if you’re a new iPhone customer, it’s only a matter of time before you notice prompts from Apple encouraging you to purchase a cloud storage subscription to host your data. 

Typically, upselling is best used to encourage customers to choose a higher-end version of a product or service they already like. Cross-selling, on the other hand, tends to be most effective when you want to introduce customers to complementary products that enhance their initial purchase. The best sales teams use both tactics at opportune times to great effect.

Top 6 upselling strategies & techniques to use in 2025

If you’re looking to drive more revenue in 2025 and beyond, upselling can be a game-changer. But to really make an impact, you need to use the right tactics. 

In this section, we examine six tried-and-true upselling strategies that can help your sales org get to the next level.

1. Use data to uncover upsell opportunities (don’t use blanket recommendations!)

Instead of taking a shot in the dark, use data to uncover upsell opportunities to make your ultimate recommendations more relevant — and therefore more effective. Rather than offering the same generic upsell to every customer, analyze each customer’s unique behavior, purchase history, and preferences to spot patterns. By doing so, you can personalize your offer to each customer, increasing the likelihood they’ll see value in the upsell.

While you might think blanket recommendations are something of an upselling shortcut, they often come across as pushy and disconnected from your customer’s true needs. By leveraging data-driven insights, you’re able to make upsell offers that feel personalized and well-timed. This not only boosts your chance of making the sale but also demonstrates you truly care about the customer, which strengthens your relationship.

2. Explore a freemium model (or offer a free trial)

If your company sells software, consider embracing a freemium model or offering free trials. By allowing customers to try your products for free, they can experience the value for themselves without having to make any major commitments. Once they see what your product can do with their own eyes, they’ll be more open to exploring advanced features or premium versions — giving you the perfect opportunity to suggest an upsell that feels like a natural next step.

The key to making this strategy work is timing and relevance. Keep an eye on when users hit limitations or show increased engagement with the free version, again taking a data-driven approach to the upsell that feels like a natural next step at the right time. By offering a seamless upgrade path, you make the transition from free to premium feel effortless while demonstrating how much more value they can get with a little investment.

3. Lock upgradable features in UI

Ever used a product where advanced features are visible but you can’t actually use them? It certainly piques one’s curiosity. 

By locking upgradable features within your product’s UI, you can create upselling opportunities by making it super obvious what each user is missing out on due to their current plan. This approach works best when features are integrated naturally into the user interface, showing customers exactly how these extras can benefit them without being overly pushy.

The trick here is to make the locked features tempting and relevant. That way, users feel motivated to upgrade to unlock them. To do this, use pop-ups, in-app messaging, and other subtle prompts that communicate the value of the advanced features — making them just out of reach but within sight to encourage customers to explore the next level of your product.

4. Remove friction from the upselling process

To increase the chances of upselling success, you need to remove as much friction from the process as possible, making it spectacularly easy for customers to say yes to your offer. The more effortless the upgrade experience, the more likely customers are to take the plunge. 

As you begin fine-tuning your upselling tactics, streamline the process as much as you can by eliminating unnecessary clicks, forms, and complicated checkout processes. Ideally, users should be able to upgrade or add features in just a few clicks.

It’s also important to time your upsell pitches strategically so they line up with customers being engaged and seeing value. Using personalized messages that gently guide them to the next step instead of interrupting their experiences with generic slop, you can create a smooth path to conversion that feels natural and easy — increasing your chances of success.

5. Pitch ideas — not products

When it comes to effective upselling, pitching ideas rather than products can create a more meaningful connection with your customers. For example, if you’re selling project management software, you might ask a customer something like this: I see that you’ve used our basic analytics tool. Have you considered our advanced reporting capabilities to gain deeper insights into how your team can work more effectively?

By framing your upsell as a solution to their specific needs, you can provide personalized suggestions that resonate more powerfully. If a customer is leveraging your email marketing service but hasn’t yet explored automated workflows, you can say: Have you thought about trying automation to save time, reduce errors, and increase engagement? In addition to demonstrating the value of your offerings, this approach also helps customers envision how additional features can make life easier.

6. Get customers involved

At the end of the day, everyone wants to belong and feel part of something bigger. By getting customers involved in the upselling process, you can create a sense of community and ownership around your products — which can make it easier to drive more revenue. By reaching out to power users before launching a new product add-on, giving them an advanced preview, and asking for their feedback, you can make them feel special and valued.

When done correctly, this strategy transforms customers into brand advocates, as they feel a sense of pride in contributing to the development of new features. When they see their input being taken seriously and used to enhance your products, they’re more likely to embrace your new offerings and share their enthusiasm with others. This is a big deal considering the majority of consumers (55%) discover new brands, products, and services via word of mouth — and word-of-mouth advertising boasts a higher research-to-purchase ratio than any other channel.

Taken together, when you win the word-of-mouth war, revenue follows.

Ways to identify upselling opportunities

At this point, you understand what upselling is, why it matters, and some strategies you can use to successfully upsell to existing customers. But you might be wondering how you can identify when the opportune time for upselling is. Next, we explore four effective strategies you can use to pinpoint the moments when customers might be most receptive to upselling.

Think about new customers first

One of the best times to upsell a customer is when you’ve just onboarded them. Since new customers have already shown interest in your core products, they may be more receptive to exploring additional solutions. By introducing relevant upsells at this stage in the relationship, you can enhance their experience while demonstrating the value and benefits of your products.

Just remember, the key to this approach is coming to the table with a mindset focused on providing value — and not being overly sales-y. Whatever you do, make sure to frame your recommendations in a way that shows how additional solutions can enrich each customer’s experience.

Use all available data

Effectively identifying upselling opportunities starts with leveraging all the data you have at your disposal. By analyzing customer behavior, purchase history, and engagement patterns, you can gain valuable insights into what additional products or features might best resonate with your customers. For example, if data shows that a customer frequently uses a specific feature of your products, you can adjust your upsell accordingly.

While you’re at it, leverage customer feedback and CSAT scores as further clues about upselling opportunities. If a user is enthusiastic about certain features or calls attention to challenges they face, this information can guide your upselling strategy. At the end of the day, everyone wants to feel heard. By listening to what customers are saying and using their feedback to guide your recommendations, you’ll have more success with upselling.

Track renewals

Tracking renewals is a powerful way to identify upselling opportunities and gauge customer satisfaction. When a customer opts to renew their contract, it’s a clear sign they’re finding value in what you offer. And it also presents the perfect opportunity to introduce additional products or features that can further enhance their experience. 

By monitoring contract renewal dates, you can time your upsell pitches strategically, pitching complementary solutions when the customer is already reaching into their wallet.

Work with your marketing and support teams

Collaborating with your marketing and customer support teams can also help you identify upselling opportunities within your existing customer base. These teams often have direct interactions with clients and can provide valuable insights into their needs, preferences, and pain points. 

By leveraging feedback from customer interactions, you can gain a deeper understanding of when and how to present upsell options that align with their interests and challenges. For example, if a support team is frequently fielding questions about specific features, it could indicate there’s demand for an upsell related to that capability. 

Additionally, by analyzing customer behavior and engagement metrics from marketing, you can identify trends that indicate readiness for upselling — like increased interest in collateral related to certain functionality or specific feedback from customer surveys. By aligning your efforts with others on the team, it ensures your upselling efforts are timely and resonate with customers — improving the chances of a successful upsell. 

Here’s how LeadIQ uses upselling strategies

Here at LeadIQ, we’ve baked upselling into the foundation of our business, offering four different tiers of our product, each with different features and capabilities.

Our free tier helps teams like yours dip their toes into the world of LeadIQ without having to make any commitment at all. When you get started with LeadIQ for free, you can test out our platform with 50 verified work emails per month, five mobile phone numbers per month, 10 accounts tracked, and 40 emails generated with AI. We’re confident new users will see the value our platform delivers out of the gate and ultimately opt to upgrade to a higher paid tier.

On top of this, we have several optional add-ons that are only available to customers that have annual plans — like the ability to instantly enrich Salesforce data and the ability to track champions, buyers, and power users when they switch jobs. 

We know how our capabilities can transform sales teams — we use LeadIQ every day ourselves — so we’re eager to get teams like yours in the door because we think you’ll be blown away by what you see once you’re inside.

To see what we’re talking about, take LeadIQ for a free test drive today.

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