Top Cross-Selling Strategies for B2B Sales

What is cross-selling?

In today’s tricky economic climate, sales teams need to get creative to navigate shrinking budgets and slower deal cycles. 

Cross-selling — the process of offering complementary products or services to existing customers — is one effective technique that can help reps overcome these challenges. 

Unlike upselling, which involves convincing customers to buy a more expensive version of a product, cross-selling recommends additional items that enhance the original purchase. For example, a company that sells project management software might offer existing customers time-tracking software alongside it.

While many people associate cross-selling with ecommerce or B2C — think being offered a phone case to complement your brand-new smartphone — more and more B2B sales teams are using it to make products stickier and boost lifetime value. 

These days, finding new customers is more challenging than ever; cross-selling helps teams sidestep that struggle by deepening relationships with existing customers. At the same time, it also enables sales teams to learn from customers about potential new features or services that could be developed to meet evolving needs.

If you’re looking to increase revenue with cross-selling, you’re in the right place. In this piece, we examine the top cross-selling strategies B2B sales teams can use in 2025. But before we do that, let’s take a step back and look at the benefits of cross-selling and the best times to use this sales tactic.

What are the benefits of cross-selling?

Sales teams that use cross-selling benefit from:

• Increased revenue per customer, as customers purchase additional products and services, boosting the overall revenue from each client;
• Improved customer relationships, with reps demonstrating they understand and can anticipate customer needs; and
• Enhanced product stickiness, with products becoming more essential to customer workflows by integrating complementary tools.

Best times to utilize cross-selling strategies

Cross-selling isn’t just about boosting average contract value (ACV). It’s about solving real customer problems and improving their experiences.

After all, simply pushing additional products for the sake of a bigger deal can overwhelm prospects, leaving them feeling uneasy or pressured. 

Instead, reps should carefully assess each customer’s needs and recommend complementary solutions that genuinely enhance their workflows or solve pain points. By focusing on creating value and striking at the best times, reps can build trust and foster long-term relationships — and not leave customers feeling like they’ve been taken advantage of.

When you’re ready to try your hand at cross-selling, here are the best times to use the tactic:

• Throughout the initial sales process. The initial sales process is a great time for cross-selling because it allows reps to approach it as a discovery phase, learning more about the customer’s broader needs and offering custom solutions early on. To avoid feeling pushy, reps can ask open-ended questions to understand challenges and suggest relevant products that genuinely address those needs.
  
  
• During the final steps of a transaction. When a deal nears the finish line, it’s an ideal time for cross-selling because prospects are likely already familiar with the value of additional products but just need a little nudge to commit. At this point, reps can gently remind them of their initial interest and offer a limited-time discount, framing it as a way to help them save while enhancing their overall solution if they act within the next three months.
• After the sale or upon renewal. When a deal is done or a contract’s up for renewal, reps can try cross-selling tactics because they understand which features and services the customer uses the most, which makes it easier to offer complementary products that enhance their experience. To avoid coming across as pushy, base cross-sells on data-driven insights, showing how the additional products can make life easier while framing it as a natural next step.

How to find the best cross-selling opportunities & strategies for your business

Every business is different. Even if two businesses sell the same product, how they go about selling that product will determine the best cross-selling opportunities.

For example, a data enrichment business that utilizes a freemium SaaS model will likely have different cross-selling opportunities than a business using an enterprise model where customers need to talk to a sales team member before signing a deal.

To understand the best cross-selling strategies for your business, use these three processes.

Analyze marketing efforts

Here at LeadIQ, we’re big believers in sales and marketing alignment. In the ideal world, sales and marketing should be on the same page, helping customers and prospects solve the same problems. By analyzing your website and determining which pieces of content are resonating the most with existing customers, you can gain a wealth of insights and leverage them to identify cross-selling opportunities.

Analyze sales calls

As AI makes its way into sales engagement platforms, it’s easier than ever to review your team’s phone calls with prospects and customers, identifying key takeaways that can help you uncover cross-selling opportunities. For example, your customers may express wanting your technology but being unsure how to get their team to adopt it. In such a scenario, you might be able to cross-sell product training or premium support services.

Analyze customer support

Are you seeing a consistent problem being raised on customer support channels or a specific FAQ or doc that’s being visited frequently? If so, you might be able to find a cross-sell opportunity or even get ideas for a new product enhancement. 

Cross-selling strategies for 2025 (and beyond!)

As we all know, sales is a completely different beast than it was just a few years ago. From the pandemic to the rise of AI sales tools, the profession is going through a transformation we haven’t seen since we moved from rolodexes to CRMs!

With this in mind, we’ve developed a list of the best modern cross-selling strategies teams can use today. Keep reading to learn more about the strategies that make the most sense for your sales org.

Cross-selling strategy #1: Keep sales teams involved post-close

While many teams use SDRs to prospect, account executives to close deals, and customer service teams to onboard customers, this approach may cause your team to miss out on cross-selling opportunities.

For starters, information can be lost from the handoff between SDRs and AEs. But that’s a story for another day. 

What often has an even bigger impact on customer satisfaction and retention is the hand-off after signing a deal — where the AE introduces the customer to the support team, which handles everything after the documents are signed. When customers onboard, they often uncover problems they didn’t know they had or learn new things about your technology they weren’t aware of.

By having the same AE who closed the deal reach out to the customer throughout the onboarding process and at regular intervals after (which you can automate!), you can help ensure customer continuity and create cross-sell opportunities just by leaving lines of communication open.

Cross-selling strategy #2: Offer expert consultations

Whether you’re cross-selling to an existing customer or a new prospect, offering third-party expert consultations can be a huge differentiator. 

For example, if you’re selling a B2B marketing automation solution, you can offer a free 30-minute conversation with a third-party subject matter expert free of charge to the prospect. 

This conversation may or may not have anything to do with your technology. Either way, the offer not only builds trust but also can help the expert identify potential cross-selling opportunities throughout the discussion.

In the case of marketing automation, the prospect may be looking for a way to automate newsletter sends. But in talking with the expert, they might also discuss potentially implementing a chatbot on their website — which could be a service your company already offers.

In addition to helping you uncover new potential cross-sell opportunities, the third-party expert can also help build rapport with prospects and customers because their reputation goes further than your company’s word alone. After all, they’re putting their name on the line by working with you — and your prospects inherently understand that.

Of course, you’ll likely have to pay these experts to work with you. We suggest looking at folks your leadership team may already know — or utilizing networks of investors if you have VC funding to find folks they know.

Cross-selling strategy #3: Incentivize onboarding completion

If you’re selling a freemium B2B SaaS solution, you might find that customers sign up for your tool, ignore all the tips and onboarding support you offer, get frustrated, and never come back. 

This is something we’ve experienced ourselves at LeadIQ with our free Chrome extension, and we’ve learned that the best way to ensure teams actually complete the onboarding process is to incentivize them.

Depending on your preferences, this could mean giving them a free month to trial the premium version of your tool or giving them a discount for a period of time. Better yet, you could offer additional credits or a feature set only offered in your highest tier. 

With the right approach, this would not only encourage customers to complete your onboarding process but also make your solution sticker. If the stars align, your customers might fall in love with the higher-tier feature, discover it’s something they can’t imagine working without, and then go on to purchase a subscription when the trial ends. 

If you’re selling into a bigger enterprise and find out that leaders are frustrated upon renewal because the team didn’t actually adopt the tool, you can cross-sell them a personalized onboarding training session. 

Cross-selling strategy #4: Ensure customers know about new features & services with personalized outreach

Did your company recently launch a new feature set, product, or service? Chances are your existing customers don’t know about it — even if you’ve sent them reams of marketing emails announcing the new offering. After all, people are busy, and most folks simply don’t have the bandwidth to read marketing emails regardless of whether the information inside is valuable to them.

Instead of relying solely on marketing emails, we recommend having your sales and support teams reach out to customers with personalized recommendations about how these new additions to your offerings can help them accomplish more. While this takes a bit more work, the results really do pay off. Plus, you can use an AI-powered email writing assistant to jumpstart the messaging process for you, saving a ton of time along the way. 

At the end of the day, people love to feel taken care of and that they’re receiving a personalized recommendation. By going the extra mile and letting customers know you a new feature or product might make their lives easier — based on a deep understanding of how they’re already using your products — they’re more likely to agree to schedule time with your sales team to explore the new offering further.

Once you have them on the line, you might identify even more cross-selling opportunities beyond the new product feature you mentioned in your outreach and be able to cross-sell additional solutions.

How will you utilize cross-selling strategies?

Sales teams large and small are struggling to hit their numbers in today’s challenging environment. By leaning more heavily into cross-selling, reps may have an easier time closing bigger deals by selling more to existing customers.

Ultimately, each company is unique, which means that different businesses will have different levels of success with different cross-selling strategies. To find out what works best for your team, we encourage you to test the waters with each of these strategies to find out what’s most effective.

And of course, we wouldn’t be doing our job if we didn’t act on our own advice. So while we have your attention, have you heard about LeadIQ Scribe, Contact Tracking, and Refresh?