Quick—what part of your job do you enjoy the least? If you’re like most salespeople, you probably said prospecting. All the cold emails, the endless follow-ups, the calling, and the relentless slog of “no” after “no.”

While there’s a time and a place for prospecting, if you’ve already got a long list of current clients, you may be wasting your time on finding new ones.

Why?

Because you can upsell your current clients to a premium product more easily than you can bring on new customers. And when you do so, you can drive more revenue, greater client loyalty, and higher commissions than going the old prospecting route.

This guide shows you how to upsell like a pro. Inside, we’ll look at the massive benefits of upselling as well as The Proven Product Upselling Framework that takes all the “huh?” out of this underutilized sales strategy.

What Is Upselling?

Upsell Definition: To effectively encourage current clients to purchase a more expensive, upgraded, or superior version of the product they have now.

Simple, right?

When you convince your current clients to purchase a newer version, you’re offering an upsell, meaning a better version than what they’re using today.

This, of course, deviates from the normal routes of prospecting (i.e., attracting new customers) because it focuses on your existing customers.

Some examples of upsells include:

Higher tier membership offering better support
Different models with added features
Premium packages with more products included
Added product warranties
Increased personalization

Upselling vs. Cross-Selling

Upselling is often confused or conflated with cross-selling. But in fact, the two are slightly different. Let’s take a look at the definition of cross-selling to see how.

Cross-Selling Definition: To effectively encourage current clients to purchase an entirely new product, usually on the basis of the product they have now.

Rather than getting an upgraded version of a product, they’re getting a new one entirely.

Let’s look at an example.

Say you’re shopping for organic vitamin C supplements on Amazon. You’ve found a brand with some great reviews, so you decide to purchase from them. But as you’re about to add the supplement to your cart, you notice they offer a higher potency version and decide to upgrade to that version instead.

That is an upsell.

As you make your way through the checkout process, you’re taken to a “Because You Liked…” page that offers products you may like based on your purchase of the supplement. Products like other supplements, natural teas, and organic skincare products.

That is cross-selling.

See the difference?

Why Upsell At All?

Now that we’ve got a better handle on what upselling is (and what it isn’t), the question becomes, “Why do this at all?” I mean, why work on a whole new process to bump your existing clients up to another version?

Should you even bother?

As you might’ve guessed, the answer is a resounding “Hell yes!” But why? What makes focusing on the upsell sales technique so beneficial for you?

There are four main reasons why upselling beats out traditional prospecting.

It…

Is easier than finding new prospects
Drives more revenue
Instills greater loyalty
Enhances personalization

A. Easier Than Finding New Prospects

First and foremost, focusing on driving new sales from existing clients is substantially easier than closing deals with new customers.

Here are some stats to drive the point home.

Prospecting and qualifying leads are the top challenges for at least 1 out of 3 salespeople (HubSpot).
You have just a 5 to 20% probability of successfully selling to a new prospect in most industries. If you’re selling to an existing customer, that probability jumps to 60 to 70% (Marketing Metrics).
It cost 5X as much to attract a new customer compared to retaining an existing one (Invesp).

When you put your efforts into the clients you already have, you’re bound to see more success than blind prospecting.

“We all know the stats that show how hard it is to get a new customer compared to keeping your existing ones. So if you show genuine curiosity in how things are going with existing clients, it means you've got to spend less time scrapping about creating content, less time making cold outreach because you're maintaining your existing customer base through being genuine through being passionate about their outcomes, which in result, is going to help you hit your quotas or break your quotas and obviously make more commissions.” – Interview Sam Dunning, Marketing Expert

B. Drives More Revenue

When you work with existing customers, you’re going to drive more revenue (and earn higher commissions) than seeking out new leads.

Let’s look at the numbers.

Increasing customer retention by just 5% drives a 25 to 95% increase in profits for businesses (Invesp).
Repeat customers spend 67% more on purchases than new customers (BIA).
Nearly 2 out of 3 businesses with strong customer loyalty make more money from these customers than it costs to retain them (Aspire Power Solutions).

It isn’t just easier to work worth existing customers then. It’s also much more profitable. Convinced yet?

C. Instills Greater Loyalty

The more you can get current clients to invest, the more likely they are to remain loyal—provided you follow through on your promises, of course.

That boosted loyalty increases their customer lifetime value (which is great). But equally importantly, it skyrockets the chances of earning a referral from those clients.

And referred customers are worth their weight in gold.

Here’s why.

Referred customers spend 15 to 25% more on their first order, make more repeat purchases, have double the lifetime value of non-referred customers, and are 3X more likely to refer their friends to your brand (Mention Me).
Customers acquired through referrals have a 37% higher retention rate than clients brought on through other means (Deloitte).
Referred customers have an 18% lower churn rate than other customers (Wharton).

Boost loyalty, earn referrals, and rake in the profits. What’s not to love here?

D. Enhances Personalization

Finally, when you upsell your current clients effectively (using the framework below), you’re demonstrating that you understand their needs. You get them. And when you show that, you’re doing wonders for rapport building.

Let’s look at just a few more stats.

Nearly all (99%) marketers agree that personalization helps advance customer relationships, with 78% claiming it has a “strong” or “extremely strong” impact (HubSpot).
Only 13% of customers believe that a salesperson can truly understand their needs (Brevet).
More than 2 out of 3 (69%) buyers report that the best way to make the buying experience positive is by listening to their needs (HubSpot).

Upselling isn’t just about bringing in more sales. It’s about showing your current clients that you really do understand their needs. And that can go a long way.

The Proven Product Upsell Framework

Clearly, there are some very real (and very lucrative) benefits to upselling your current clients.

But let’s face it, no one likes change. And unless you can really sell an upgrade, you’re likely to hear a lot of “Thanks, but no thanks.”

That’s why you need to take a strategic approach. One that zeroes in on paint points, offers quantifiable benefits, touches on risks, and drives real urgency.

Enter The Proven Product Upsell Framework. Successful upselling here we go!

This framework has seen real-world success in turning lukewarm clients into enthusiastic buyers of upsold products. And when implemented properly, it takes the question mark out of upselling completely.

All you have to do is:

Document Current Results
Explore the Changing Needs
Highlight the Risk of Not Switching
Give an Instant Discount

1. Document Current Results

“Every single move you're going to make, whether it's a renewal or an upsell of any type, starts with identifying and documenting results, anchoring and justifying their faith in you.” – Interview with Tim Riesterer, Chief Strategy Officer of Corporate Visions

The first step of the framework is to document how you’ve already helped your client. This is the sturdy, logical foundation on which your upselling pitch is built. After all, B2B buyers make decisions on hard numbers, not just sales savviness.

When it comes to new vs. current accounts, it’s all about how you treat the status quo.

For instance, with new accounts, you want to attack the status quo. Productivity could be better. Efficiency could be better. Bottom-line earnings could be better.

But with current accounts, you’re actually attacking and defending the status quo. You’re defending it because you don’t want clients to head to your competitor. And you’re attacking it so you can convince them to upgrade to your premium product.

There are a couple of ways you can do both at once. But the best I’ve found is by sending them a value-rich quarterly report.

Create a Client Quarterly Report

The quarterly report isn’t difficult to create. And sending it to clients before having an upsell conversation is incredibly effective at driving change.

In it, you should include six separate elements.

Your Earned Results – What results have you and your product earned for the account? How have you improved their business, streamlined their processes, and boosted their revenue? Get into the weeds here with hard, quantifiable numbers.
Review of Previous Buying Process – This should be a quick reminder that reconfirms the client did their due diligence during the original selection process. This is especially helpful if decision-makers in the account have changed roles. But secondly, it also reinforces the pain of going through all that again with a competitor.
Sharing of New Industry Insights – This is where the real value starts to kick in. What industry issues are coming down the pipeline for the client? What should they anticipate next month, next quarter, and next year? And how can you help them weather that change?
Detailed Competitor Improvements – Your product may be very similar to your competitor’s (that’s just the way it is sometimes). But when you’re working with existing clients, that can actually work to your advantage. If you can explain to your client that there are similarities between the two ranges of products, they’ll likely agree that there’s little reason to change things up.
Your Own Detailed Improvements – In this section, explain how you and your company have been improving your products. What new features have you been developing? How do they compare to your competitors? And how can they help the client?
Highlight the Cost of Change – Lastly, wrap up the document by giving a brief summary of the cost of changing considering everything discussed so far. This is also a fantastic place to start introducing the upsell products you hope to convince clients to buy.

Upsell Pro Tip: Your report should aim to offer value, not just prime the client for an upsell. As such, you need to frame it as a source of information they’ll actually want.

If it’s a blatant and shameless attempt to push them towards purchasing a new version of a product they already have, it can have a serious backfire effect that spoils the rest of the framework.

“When we provide value for someone, it's giving them the tools to make a better, faster, more effective, more efficient decision than they would have without our input.” – Interview with David J.P Fisher, Sales & Networking Expert

2. Explore the Changing Needs

Your quarterly report has already laid a solid foundation for this step with the industry insights, detailed improvements, and cost of changing aspects.

With that information in hand, it’s time to extrapolate.

How will your client’s business change in the upcoming years? What are their competitors doing that they aren’t? And do the products your client uses now suitable for offering that same competitive advantage?

Equally importantly, where does your client want to be in the future? What goals can you help them achieve that might otherwise be out of reach?

It’s time to put your research skills to work here. As the more nuanced and specific you can get, the better.

Offer the Solution

When you’ve identified your client’s changing needs, it’s time to talk about how your product addresses that need gap.

How does your premium product help them achieve their goals? How does your premium product get them to where they want their business to be faster than ever?

Using “what if” scenarios here is a great sales tactic. Try getting them to vividly imagine what it would be like if they achieved their future goals using your product.

Beyond simply priming them for a “yes” answer, this technique also helps the client clearly see that something is needed to achieve those goals. And if you’ve done your job, they’ll know it’s what you’re offering.

Upsell Pro Tip: Research is going to play a major role at this stage of the framework. If you can pinpoint some of the biggest pain points and growth opportunities your client is facing, you can leverage them to better sell your premium product.

Plus, it also shows you’re truly invested in the relationship and understand their changing needs. And that builds trust.

“I think the age-old relationship-building, rapport-building, really doing our research and understanding that person and the organization and making that connection, finding a way that we can demonstrate our expertise and show trust. I think that's critical and probably more important now. We just need to do it in a different environment, because some of the other things we used to do, like break bread together or physically shake hands, we can't do those anymore.” – Interview with Ray Makela, Author, Speaker, & Business Executive

3. Highlight the Risk of Not Switching

Once the buyer understands that their needs have changed and you can offer them more value than before, you need to pull on the other end of the spectrum of pain.

So far, we’ve been focused on how things are going to get better when they work with you. Now though, we need to shift to discuss the pain they will face if they don’t.

Now we need to double down on the fact that there is a risk to the buyer if they don’t keep up and enable us to support them.

This turns the upsell from a “nice to have” to a “necessity” in the mind of the buyer.

You can do so by tapping into the six forms of risk.

The 6 Forms of Risk

The risk of not changing comes in six different forms. If you can explain one or more of these forms of risk of not changing to your buyer, you’ll immediately get them pushing towards an upsell contract.

Physical – This includes dangers to your buildings, equipment, and people. This can hurt your business by resulting in lost time, repair costs, legal action, and reputational harm. Has the buyer changed properties since your original deal? Can your product help reduce the new risk they have in their new buildings?
Strategic – This risk type involves roadblocks to achieving organizational goals. Has the client changed their business, marketing, operations, product, or sales strategy? Can your product help them manage this change or reduce the downside if their new strategy doesn’t work?
Regulatory – Businesses are governed and guided by a wealth of legislation, regulation, and responsibilities, both mandatory and voluntary. The risks of failure to be compliant can be severe, including legal action, fines, penalties, and even closure. Have their compliance risks changed? How can your product reduce this new risk?
Operational – Operational risks are problems that can happen during the day-to-day running of your buyer’s business. They can include things like human error, inappropriate staff behavior, or systems failure. Can your product reduce the new risks that now exist in the buyer’s operations that didn’t exist before?
Technological – With the benefit of new technology comes increased risks. Cyber-attacks, leaking important information, or system downtime can be devastating for a business. If your buyer has increased their reliance on technology, can you reduce their new risks with your product?
Financial – From economic uncertainties and volatile financial markets, the move towards sustainable finance gets increasingly important as a business grows. If your buyer has increased in size, production, or headcount since you originally sold them, has their financial risk increased? Can your product help reduce this financial risk?

Upsell Pro Tip: Don’t overdo it when hammering in the risks. Usually highlighting just one or two will get the ball rolling. But be sure to pinpoint which are most important to the buyer.

“In exchange for giving you the time to have one of these meetings, you're going to be bringing the kind of evidence that is useful to them personally and professionally in that organization and the project or job that they're working on.” – Interview with Tim Riesterer, Chief Strategy Officer of Corporate Visions

4. Give an Instant Discount

By now, you’ve proven to the client that you’ve brought them real, tangible value with your product. You’ve demonstrated that their needs (and the industry at large) are changing around them. And you’ve given them a few reasons to sweat by outlining the risks of not upgrading.

For some clients, these three steps alone will be enough to motivate action. But for others, fear of change may still be causing some hesitancy.

That’s when it’s time to break out the urgency-busting big guns—the instant discount.

This instant discount should be the motivator that gets the client to sign on. But this isn’t any discount. Instead, it’s a time-based discount. And it’s only valid until the deadline is up.

Urgency is the last straw before deciding to buy in. It’s the straw that broke the camel’s back, as it were. And if you’ve successfully performed the three previous steps, it should be the final piece of motivation your client needs to purchase your upsell.

Trigger Event Best Practices

Below are some best practices to follow when creating your trigger event.

Avoid Fake Urgency & Scarcity – These ploys, when uncovered, only breed animosity and degrade your client’s loyalty (a death sentence for your rapport).
Don’t Get Too Flashy – Too many buzzwords and urgency pushes will rub buyers the wrong way. Instead, be clear, confident, and respectful. Remember, you’re offering value, not trying to meet a quota.
Personalize If You Can – If you’re only cutting a deal or giving a unique discount with them, let them know. And tie back the deal (e.g., lower price) to the client’s goals (e.g., coming in on budget).
Keep the Pressure On (To an Extent) – There’s nothing wrong with sending a few helpful reminders that your trigger event is ending soon. Just be careful of getting too pushy here.

Upsell Pro Tip: A trigger event doesn’t always have to be price-related. You could also offer complimentary onboarding, expert consultations, additional products, or other creative incentives. But remember, they all have to be tied to a deadline to drive real urgency.

“Understanding your audience is always the first step. So, I think so much of sales is doing your homework, doing your preparation, and knowing what those trigger points are. What are the things that are going to move these people to actually respond in the way that I want them to? So, that's where I always start, is let's figure out who our customer is, let's figure out our audience, and let's speak their language.” – Interview with Robbie Crabtree, Senior Lecturer at MIT

Wrapping Up

The upsell is one of the best ways to generate more revenue, instill more client loyalty, and even bring in more referrals than ever. Best of all, upselling to existing customers is more efficient, effective, and profitable than fishing for new clients.

And to do it strategically (and successfully), all you have to do is:

Document Current Results
Explore the Changing Needs
Highlight the Risk of Not Switching
Give an Instant Discount

So before you go spending 80% of your day on prospecting, try reaching out to your current buyers and upselling them on a premium version of their current products. When you follow this framework, you’ll be surprised how easy earning a “hell yes!” can be.

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