9 Non-Sleazy Strategies for Upselling Your Customers



Guest Writer

⏱ Reading Time: 9 minutes

When you’re trying to make sales, it’s only natural to want to expose buyers to as many potential purchasing ideas as possible. And when maximizing sales, one method towers above the rest: upselling.

Upselling seeks to persuade customers to add extras to their shopping basket, and it’s also a very lucrative technique.  As Pacific Crest reported in its 2015 SaaS Report, companies that upsell experience much faster growth rates driving profits higher.

🚀Read Customer Experience Guide: How to Put your Customers First?🚀

Upselling also helps to achieve maximum conversions, with minimum effort. As marketing expert Amy Gallo has noted in the Harvard Business Review, the cost of acquiring new customers is between 5 and 25 times that of extracting sales from existing buyers. In those circumstances, upselling is a great way to boost the efficiency of sales teams.

However, upselling can alienate customers and dent a company’s reputation. So it’s not without its problems. Because of this, here are some suggestions about how to upsell well, while keeping the  risks low.

Is Upselling a Sin Anyway?

Before we explore how to avoid the pitfalls of upselling, it’s important to stress that the upselling itself isn’t a mortal sin.

People have been using similar business tactics for thousands of years. From the lowliest market vendors to the IT corporations that straddle the globe today, sellers have long sought to persuade buyers to add extras that they wouldn’t normally have considered.

And why not? After all, we’re all in the game to make money, and buyers are capable of assessing purchases like grown-ups.

With the dominance of eCommerce, upselling has become unavoidable. Online catalogues and search platforms now have to offer suggestions about products which meet client needs. Companies that fail to do so accurately are falling behind.

That’s the very weakest end of the upselling spectrum, but there are many more aggressive varieties which can be much more risky. Sometimes, they can feel downright sleazy for customers. That’s when companies start to cause real damage to their reputation.

However, it doesn’t have to be like that. So let’s look at 9 non-sleazy ways to upsell sensitively and intelligently, while still receiving maximum bang for your buck.

A comic by Dilbert about upselling

Picture 1. A comic by Dilbert 

Strategies for Upselling

1. Start Slow, and Understand Your Audience Inside Out

First off, upselling techniques need to be informed by the needs of your customer base. Bombarding customers with suggested purchases that have zero relevance to their lives is a rookie mistake, and a sure-fire recipe for failure.

Instead, savvy upsellers research the desires of their audience. They build buyer profiles which take into account customer needs, and they design recommendation delivery mechanisms that meet those needs.

Speed matters, too. If need be, build recommendation systems slowly, running A/B testing to perfect their outcomes. If there are flaws, rolling out site-wide upselling can be an absolute disaster, so proceed with caution.

Read How to Surpass Customer Expectations Using SaaS Tools

2. Deliver Upgrades and Bonuses That Make Sense

When you know more about your audience and its motivations, you’ll be ready to create a structure of add-ons that corresponds to their desires. Learning from established companies is a good idea here.

For instance, upgrades are something that Apple does well. When you visit Apple’s site to buy a new MacBook, you will automatically receive upgrade recommendations. These cover a huge range of possible purchases, from bundled apps to peripherals and memory. But they aren’t random.

Apple works from the basis that you want a specific model of MacBook. They then offer upgrades based on that decision – and that decision alone. The company has learned the hard way that directing users to irrelevant products yields less than stellar results.

3.  Show Your Awareness of the Dangers of Online Tracking

If you’re selling online, there’s a good chance you are using tracking cookies to monitor site visitors. And that’s understandable. Cookies let us track how visitors use our sites, referral information, and even how customers move mouse cursors. They can also allow us to store customer data for future reference.

Without tracking cookies, making lazer-like recommendations for online upselling would be very tricky indeed.

Online tracking

Picture 2. Online tracking is controversial

However, tracking customers online is a controversial issue. People hate privacy breaches. That’s why GDPR exists, and why Apple and Google are taking steps to eradicate cookies from their services.

If you need to use tracking tools, be open, and adhere to all GDPR requirements. But don’t stop there. Businesses can gain customer trust by discussing tracking and cybersecurity. They can show their awareness of individual privacy, and even make recommendations about how to stop being tracked online.

Whether you use blogs, email newsletters, or direct contact, discussing customer privacy can boost your image, and even make customers more willing to convert.

4. Understand Which Customers Are the Best Upselling Targets

So far, we’ve been talking as if upselling is something that applies to every visitor to a company’s website. In some instances, that’s true. Take Amazon, which targets every single visitor immediately.

The problem is that hardly any companies operate like Amazon. Most of the time, different rules apply, and upsellers will need to work out who to target to maximize their ROI. This means that you need to know how to reach a core audience, not every single site visitor. And there are a couple of ways to do this.

  • You could use email newsletter subscribers as your core group. Sign-ups should be engaged with your brand and more likely to convert.
  • Data from interactions with customer service teams can identify customers with specific interests.
  • Data from customer histories should show which products customers have purchased, and what they are missing.
  • Feedback from tailored marketing surveys.

Read 7 Best Customer Retention Tips to Boost Your Business

5. Follow up Solid Service With Proactive Upselling

Timing also matters. Ideally, you should upsell to customers when they are most likely to convert. Generally, that isn’t the first time they interact with your website or sales team. In fact, customers are more likely to upgrade their purchases after they have experienced what your company delivers.

That’s why free software trials are so ubiquitous. Vendors know that buyers want to get a taste for what’s on offer. When they have tried the VPN, SEO keyword tool, or file converter involved, customers will know more about what they want. That’s when upselling kicks in, not before.

This applies pretty much across the board, from selling powerboats to gym equipment. However, every customer journey is different.

That’s why it’s important to model upselling funnels from initial contacts to purchasing, feedback, outreach, and repeat purchases. By modeling successive customer interactions, you can get a good sense of exactly when to send emails or make calls.

6. Mix Upselling and Informative Content

For many smaller businesses, the best approach to upselling involves using content marketing techniques like blogging, writing guest articles, and social media posting. All provide ways to reach out to customers in non-sleazy ways, and they all have their own unique role to play.

Take blogging, for example. You can’t reach out to individual customers via a blog. But you can explain to a wider audience why your upselling emails or upgrade structure is worth engaging with. That way, you can build both interest and trust among the people who are most likely to be receptive to upselling techniques.

Try to frame your content as useful, relevant, and personal. Talk about how customers can use your products, and always outline how buyers will benefit from spending extra cash. You can’t communicate this via catalogues or online stores, but blogs and articles are excellent ways to do so.

Read 5 Steps to Success in Content Marketing For SaaS


7. Always Be Open About How You Structure Your Upselling

Using manipulative language to deceive buyers with outlandish claims about what your products can do is one of the sleaziest upselling techniques around. And it’s closely rivaled by sellers who spring extra costs on buyers from nowhere, like a kind of marketing ambush.

Don’t be like those marketers. Instead, be transparent about what you have to offer, and how different upgrades compare. And be clear about the benefits attached to each extra dollar spent by customers. Take this ad for razors, for example. It’s clear, visually appealing, and comprehensive.

Upselling razors example

Picture 3. Be transparent when upselling

Customers want in-depth (but not complicated) information about what they are getting. Sure, you can use humor and creativity, but don’t be vague. Be confident without being pushy, and focus on providing information that’s important to each potential buyer.

8. Mobilize Your User Base to Motivate Potential Purchasers

Even with the best descriptions, the clearest pricing information, and perfectly timed emails or phone calls, customers can still resist the urge to make an upgrade or additional purchase.

There’s nothing unusual about that. Most of us are sceptical about upselling. We know that companies are trying to extract maximum revenue from every customer, so we look for proof that what we are being sold is worth the money.

That’s where social proof comes in handy. If you display feedback from previous customers, buyers will be able to see that no-one is deceiving them. Include detailed reviews (they don’t need to be 100% positive). You’ll find that buyers respond well to evidence from third parties, even if it is a little rough around the edges.

Moreover, try to attract external comment via blogs, reviews, and social media influencers. You can add this to emails or landing pages, boosting the credibility of whatever is being upsold. It all adds to the weight of your sales materials, while boosting your brand reputation as well.

Read How to Build Brand Loyalty?

9. Track Upselling to Perfect Your…Upselling

Finally, successful upselling strategies can help you become an even more effective upseller. That might sound odd at first, but here’s how it works.

Firstly, track the products which upsell most efficiently. At the same time, track the kinds of customers who prefer specific products. Put the two together, and you can fine-tune the way you sell in the future. In the process, you should create positive feedback loops which increase conversion rates over the long term.

This kind of analysis can go further. For instance, you might want to monitor how long customers take before they choose to upgrade or add extra features. You could also track how well purchases have met customer needs.

If you use automated recommendations, you could assess how well they are performing – and whether they are actually delivering solid returns. As we noted earlier, automated recommendations can be a major benefit, but can also turn off potential buyers.

When It Comes to Upselling Think Smart, Not Sleazy

In a business environment dominated by eCommerce, we have more upselling tools than ever before. We can deliver tailored product recommendations, send generic or individualised emails, call specific clients to ask about upgrades, or even push notifications via apps.

With so many tools, it’s tempting to take a lowest common denominator approach, and spam customers with special offers or notifications. In other words, it’s easy to become sleazy.

However, as we’ve seen, alternatives do exist. Carefully designed recommendation systems, blogs explaining the benefits of upgrades, audience research, and sensitive customer tracking all have their place. Put them together, and you can upsell without too many risks.

So take a measured approach, and don’t put your reputation on the line. Smart upselling is the way to go.

Olivia Scott is a cybersecurity enthusiast at VPNpro.com. Her key competencies include data safety, privacy tools testing, and WordPress vulnerabilities.

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9 Non-Sleazy Strategies for Upselling Your Customers was last modified: July 6th, 2020 by Martina Pranjic
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