When I was knocking on doors as a salesman, I was motivated by commission. I quickly learned that to make those hours on foot worth it I had to work hard for the sale. It didn’t take much longer to learn that even better than working hard was working smart. Working smart meant understanding human psychology, building sincere relationships with prospects, and using strategy over gimmicks or pressure. The more I learned, the more integral the cross-sell and upsell became to my in-person sales strategy. They’re an important part of my marketing strategy to this day: when combined with valuable, targeted content and used to enhance personalization, cross-selling and upselling can dramatically boost conversions.

Upselling on Foot

To sell a top-tier home security system, the first thing I’d mention to a prospective customer was our least expensive offering. They were just warming up to me, and I didn’t want to come off as too aggressive. Then, I’d simply engage them in a conversation about their home: how long they’d lived there, how many kids they had, their new landscaping—anything that got them talking about the value and emotion attached to their home. Then I’d drop another easy-to-swallow figure like, “Our security system only costs about a dollar a day.” Internally, they’d be doing the math and thinking, $30 a month doesn’t sound too bad.

Soon, the idea of buying a security system would feel like a no-brainer to the prospect. We’d talk about how the system was installed and operates, what the best placement would be for their particular home layout, and how simple it would be to get started. That’s when I introduced the upsell. I might say, “You know, I’m just thinking about the size of your house and wondering if you’d prefer our expanded system.” Or, “A lot of our customers with homes like this are using our two-way voice intercom.”

I never wanted customers to feel like I was pushing them into an upsell. My language conveyed that I was simply giving them options, sharing what had made other customers happy, and keeping their best interests in mind. I didn’t sell; I introduced ideas. I had great success with this strategy. When it came time to sign a deal, 95 percent of customers went for the upsell.

It’s the Customer’s Idea

To pull off a cross-sell or upsell, I had to be personal and practical. These qualities can be applied to digital marketing strategies as well. Personal and practical don’t sound like the sexy buzzwords we usually hear in digital marketing. But they’re big parts of an individual’s decision-making process.

Before we make a purchase, we want to know and trust the seller. Personal experiences and connections build trust so we can hand over our hard-earned money without fear of getting duped. Our practical side wants evidence that what we’re getting is worth as much or more than what we’re spending. The cross-sell and upsell work when marketers satisfy both of these deep needs. If we do our job well, our prospects convince themselves to upgrade or add on, and they feel like they’ve hit the jackpot.

Personal and Practical Optimization

We’ve all seen Amazon’s friendly, “Customers who bought this product also bought” tactic. As early as 2006, that line was responsible for 35 percent of the megaretailer’s sales. And there’s the Netflix line: “You might enjoy these titles.” Both of these subtle bits of marketing understand that the cross-sell is driven by personalization. This style of suggestion feels gentle to the customer, but it rests on powerful data.

Optimizing your recommendations is one of the most effective ways to implement cross-sell and upsell. Optimized recommendations are automated and targeted, and they use up-to-the-minute data to respond to visitors’ behavior and choices in real time.

Make the Most of Your Data

Skullcandy increased its upsell revenues by 30 percent when it started using its more effectively data to enhance product recommendations. The company uses automation to keep its product suggestions current, so visitors aren’t being shown old goods. It also uses A/B testing to monitor the success of its suggestions. The company continually makes the most of its data to increase conversions without ever resorting to pushiness.

Historical and affinity data allow you to upsell and cross-sell to individuals based on what you already know of their buying behavior, interests, and preferences. This kind of targeting feels seamless, thoughtful, and personal to the customer—especially when integrated with great content marketing.

Be Relevant and Reasonable

Relevant is another word for personal, and reasonable is another way of saying practical. Whatever you call it, it’s easy for marketers to lose sight of these basic touchstones in human decision making.

Make your recommendations so relevant and reasonable it’s a no-brainer for the shopper. In other words, focus on the easy sell. If you’re upselling, match the key features of the original product the customer was considering. And don’t try to push the customer into a significantly higher price range. Your suggestion should be a comfortable jump from the individual’s current position. People will pay more if it makes practical sense, delivers more value, promises long-term benefits, or increases convenience.

Similarly, if you’re cross-selling, don’t show your customers apples when they’re in the market for oranges. Show them additional products that are relevant and complementary or meet a related need. And less expensive cross-sells are more likely to make it into the cart. If someone has already decided to pay $30, snagging a $10 item that enhances the overall purchase is a pretty easy decision.

It’s All about Value

The bottom line is value. Added value, extra benefits, and irresistible deals are surefire conversion boosters. Today’s customers are smart: they’re savvy to marketing ploys and do their product and brand research. Just as I learned in my door-knocking days, you don’t have to work harder to convert the modern buyer, you just have to work smarter. That means offering personalized experiences that connect and build trust, and valuable products that both satisfy your customers’ practical sides and offer some frills.