Does upselling have to feel sleazy or uncomfortable?

I don’t think so, but it depends on how you approach it.

Sleazy sales reps will try to upsell everyone and anyone, regardless of whether or not the customer actually needs the additional service. But from my experience, when you focus primarily on your customer’s experience and goals, upselling benefits both you and your customer tremendously.

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Let’s dive into some winning strategies for upselling backed by data.

Check out these ten strategies for identifying upselling opportunities that are mutually beneficial below to help get you started — before you pass a customer over to a sales rep.

10 Upselling Strategies for 2024

1. Take the time to understand what success means to them.

It’s not enough to jump right into the upselling pitch without building a foundation of trust first. In fact, 29% of salespeople who upsell say establishing trust and rapport is the most effective upselling strategy — outranking any other strategy.

Upselling Stat 2

But how can you build trust effectively?

For Kathleen Rush, Sales Manager at HubSpot, it starts by approaching conversations with genuine curiosity.

“When it comes to upselling effectively, it is important to keep a natural intellectual curiosity,” she told me. “Keep asking open-ended questions about their process and a day in their life.”

She adds, “For example, I might ask a prospect, ‘Are you responsible for finding good fit leads? What happens when you find one? Where does that lead go? Who takes that lead? Can you see if they follow up? Do you wish you could?'”

Pro Tip

Asking open-ended questions keeps the conversation rolling, enabling you to uncover more information and build greater rapport.

When you know what your customers value and where they want to go, you can identify areas where additional products and services can help down the line.

2. Set and track measurable goals.

You always want to be on the same page with customers about their goals. For Dan Tyre, Sales Director at HubSpot, specificity is key.

He told me, “It’s important to get really specific around your customer’s goals and key milestones. For example, you might say, ‘From what I understand, you want everything implemented by January 1st, 2025.’ Then, you can introduce additional add-on products or integrations that can help accomplish their goals more quickly.”

Leverage what you’ve already learned about your customer’s priorities and goals, and develop an action plan with straightforward milestones to keep track of their progress.

Pro Tip

To identify an upselling opportunity later in the customer’s lifecycle, you need a way to recognize areas where the current game plan is falling short. This is where careful tracking becomes essential.

For example, if you tell a customer that she needs to devote more to her social media ad spend, you need the data to back it up. Having data to point to will bulk up your argument, and help demonstrate to the customer that you have her best interest in mind.

3. Lean into AI.

Over the past year or so, I’ve been using AI to supercharge different areas of my workflow, and upselling is no exception.

Turns out, I’m not alone. Among sales reps who upsell, a staggering 60% agree that AI will make it easier to upsell, according to HubSpot’s 2024 State of Sales Report.

Upselling Stat 1

For example, 41% of salespeople already use AI to recognize and respond to buyer emotions or sentiments, with 83% of them saying it’s effective.

Pro Tip

AI can also segment customers based on specific criteria, which allows salespeople to tailor their upselling approach and strategies depending on each group. Check if your current tech stack leverages AI.

4. Identify customers with a real need for additional services.

It’s tempting to approach every customer with the same upselling proposition. But from my experience, this cookie-cutter approach is ineffective — even detrimental.

For one, not every customer is a good fit for an upsell, and you should never, ever try to push additional products or services on someone who doesn’t truly need them. As a general rule, if you can’t explain how the additional purchase will benefit the customer’s overall goals, then it’s not an upsell worth pursuing.

For example, if you’re considering pitching your customer on an additional email marketing software upgrade, but email marketing doesn’t fit directly into her long-term plan to expand her reach, you shouldn’t force it.

If you try to sell products that have a slim chance of delivering a positive outcome to the customer, you risk causing major damage to the relationship and potentially losing her business altogether.

Pro Tip

Focus your upselling efforts on customers with an evident gap in their current plan. If a customer wants to increase her reach, but you don’t think she’s going about it the right way, there’s probably an opportunity to sell her on an upgrade.

5. Start providing value as soon as possible with quick wins.

25% of sales reps who upsell say providing consistent value is the most effective upselling strategy.

To set yourself up for a long and mutually beneficial relationship with a customer, you should focus on providing quick wins as soon as possible.

upselling stat 3

A quick win is anything that delivers immediate value to a customer. Some examples could be an audit of a customer’s existing social media strategy, an evaluation of a customer’s website to identify new opportunities for optimization, or even creating a content offer and a simple promotional plan.

Your quick win should demonstrate that you’re fully committed to bringing real returns to your customers right from day one — and that your products or services can help with that.

Pro Tip

The sooner, the better.

The sooner you can show your customer measurable success, the sooner you can deepen the relationship and prove your expertise in additional areas.

6. Pitch ideas — not just upgrades.

Your customers need to fully understand why you think an additional purchase is a good idea. They need to see how you got from Point A to Point B (the upsell).

For instance, if I pitch a customer with a blanket statement like, “I think you need to spend more on social media,” she might jump to the wrong conclusion and assume I’m trying to line my own pockets.

But if I pitched it by saying, “Your customers are more active on Facebook than any other platform. I see untapped potential with [X] that we could jump on by doing [X]. What are your thoughts?” the consumer would be more receptive.

Pro Tip

Always pitch a new upgrade within the context of an idea.

If you see an opportunity to help a customer increase her leads from email marketing, you should come up with a real plan to help her get there. Don’t just tell her that she needs to spend more — give her an easily understood plan to see where her money will be spent and how it will contribute to the overall success of her business by purchasing an upgrade.

7. Time upsells with milestones.

In my experience, timing is everything when it comes to upselling. It’s not something you should broach within the first few minutes of meeting a customer, nor should you bombard them seconds after they sign the dotted line.

While there are no hard and fast rules here, I like to approach the conversation after the completion of a successful initiative or a big milestone (e.g., reaching a new lead generation goal). It’s the perfect opportunity to take a step back and ask your customer, “What’s next?”

Conversations about the future offer a natural opportunity to bring up new ideas and projects you want to accomplish with your customers.

Pro Tip

Pitching an upsell is especially effective after helping execute a big win for your customer since she has definitive proof of your expertise.

8. Provide a transparent pricing breakdown.

Put yourself in your customer’s shoes for a moment: If someone said you needed to pay them more money for vaguely defined additional benefits, you probably wouldn’t bite. In fact, you would probably feel like they were trying to take advantage of you.

When you’re proposing an upsell, it’s especially important to provide transparent pricing information. Give your customer a complete breakdown of what you’re proposing and thoroughly explain the cost and timing involved.

Pro Tip

If a customer knows where her hard-earned resources are going, she’ll feel more comfortable about investing more money in your products. But if you’re not comfortable bringing up price, this could be a good opportunity for your customer to chat with a sales rep on your team.

9. Identify trends and apply them to your sales process.

Once you’ve successfully upsold a few customers, you’ll begin to develop a better idea of what types of customers benefit the most from additional products.

Keep track of the timing and traits these customers have in common, and incorporate trends into your sales process to proactively identify upselling opportunities on an ongoing basis.

Pro Tip

As I mentioned earlier, AI can be a huge help here. AI-powered tools can sort through vast amounts of customer data and group customers into segments based on specific criteria, allowing salespeople to tailor their upselling approach and strategies depending on the group.

10. Use social proof to convince them.

Most people need evidence to convince them before making big, expensive purchase decisions. After all, that’s the logic behind the value of customer reviews.

Before you hop on a call to try to convince your customer of an upsell, make sure you have the data and evidence to back you up from other customers or reviews who’ve found success using the add-on product.

For example, if you know the percentage of customers that use the add-on product in addition to the product the customer has already purchased, let them know that. If your company has received customer reviews from happy customers using the additional product, tell them that. 

Pro Tip

Social proof is a powerful convincing factor — so if you have those resources on hand that suggest the success of customers using both products to make your pitch more trustworthy.

Back To You

There you have it — 10 non-sleazy strategies for upselling your customers backed by data. Remember that when you focus primarily on your customer’s experience and goals, upselling benefits both you and your customer.

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