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.