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5 Ways to Upsell this Holiday Season

Posted by Emily Fanning on Dec 13, 2019
Emily Fanning

For many brands and retailers, the holiday season means high sales, but also high sales plans. Every dollar counts as you head into your final weeks of the year, and for that we want to share a few of our top tips for how to upsell in retail.

Show—don't tell—what else it comes in

This was one of my favorite tactics when I worked in retail, and it's where the importance of a strong sales team is highly relevant. When a shopper falls in love with a product, especially a piece of apparel or shoe they feel good in, it's only logical that they'll be tempted to purchase it in a second, or even third, print or color (take it from me: I'm guilty of having this sweater from our customer Melly in a whopping five colors).

It works the other way around as well: Bold Classic Blue is Pantone's Color of the Year; if your customers gravitate toward it, show them what other Classic Blue products you offer. The same goes for prints: Lilly Pulitzer is known for its print collections, and customers tend to fall in love with them before the apparel or accessory pieces themselves—making it easy to upsell shoppers with a few additional products from the suite—so take advantage of these easy add-ons if your brand offers such. 

Other options exist but not readily available in your store? Then omnichannel technology that sales associates can use to show customers all of their options is key here.

Sneak Peek Alert!

Springboard Retail's next-generation point of sale takes co-browsing to the next level. Equipped with their mobile POS, sales associates can shop alongside customers with an iPad in hand. Barcode scanners mean there's no typing in or SKU-match required; simply scan the item and its product page and all available attributes and sizes—with inventory levels by location—will pop right up.


A fresh, highly-visual modern design for these product pages mimics ecommerce browsing; your customer won't even realize they're looking into the backend of your system.

Bonus! This will also arm sales associates with additional product information to get ahead of customer questions: as long as details like material, fit, and so on are added to the product page ahead of time, it will be at their fingertips as soon as the question arises.


This kind of upselling by attribute doesn't have to be limited to apparel or footwear stores: museums should share other prints or gifts by that artist, home stores can showcase other fabric upholstered pieces come in...prints, scents even! And with Springboard's forthcoming co-browsing functionality, there's no need to have it all memorized; the product pages will show every color, size, scent—whatever it may be—available, both in store and for order.


To make this sort of in-store/order upselling seamless for the customer, we're also introducing mixed cart transactions: For the customer who is buying the solid dress off your rack but ordering the striped version for home delivery, only one sales ticket is required, yielding just one receipt. The in-store purchase versus items to ship will be easily distinguishable, yet appear on a single order with only one transaction taking place.

Current Customers: Sign up now to join the beta waiting list and be one of the first to move to our new, next generation POS in the new year!

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Advertise spend-level discounts, gifts with purchase

At some point over the last half decade or so, the spirit of Black Friday began seeping through the entire month of December. Consumers have come to expect some sort of special promotion every time they shop, and while competition and pressure to hit year-end numbers prompt many brands and retailers to match such, they must be strategic about how (and why!) they do so.

Spend level discounts are a great way to upsell; set yours up so that the promotions don't kick in until they've hit a certain spend: Spend $50, take 10% off; spend $100, take 20% off, etc. As a consumer, I found myself spending nearly $50 more with one retailer over Thanksgiving weekend, just so I could hit the next discount tier (I'm not proud of it, but they got me!).

If your main objective is instead to move through inventory, change the promotion criteria to inventory-related requirements: take 15% off when you buy 2 items, 20% off 3 items, etc. (Springboard Retail allows you to quickly and easily set up promotion rules so that they automatically kick in at the POS—no manual counting or calculating on your end!)

Strategically accessorize and merchandise

Home stores should test grouping products by room—pillows with matching throws, cookbooks with kitchen accessories. Gift stores will see success in organizing merchandise by recipient or theme—self-care gifts, travel accessories, for the hostess, for teachers, for mom. And for apparel stores, it should go without saying that mannequins must be dressed head-to-toe: Jewelry, handbags, accessories...layer it on so shoppers are tempted to add the entire outfit to their cart.

The same goes for your staff: A few pieces of allowance apparel and a generous employee discount mean you can require your sales associates to be uniformed in what you're selling. It's an easy way for them to show off entire outfits: how to style a certain sweater, or what top might match that skirt. Whether you're wearing it live or not, get vocal too: tell customers what else you have that would serve as a good complement to the room, outfit, or gift. Again, our next generation POS will make this easy with your entire catalogue at your fingertips.

Offer buy online, pick up in store

For the customer journey that starts online, BOPIS is the key to upselling: More than half of all buy online, pick up in store transactions end with customers making an additional purchase once in store.

For more specifics on implementing and creating a superior BOPIS experience for your business, check out this recent webinar!

Add-ons at the cashwrap

Just like the tabloid display in the grocery store line, this is important real estate for low-price point add-ons, and in this season's case, easy stocking stuffers. As the line moves, the customer doesn't have time to second guess what they just picked up; it's impulse shopping at its finest. Target's Dollar Section has become infamous for this. Paper Source is another retailer that sucks me in every time: last week I found myself adding some champagne gummy bears and Ruth Bader Ginsburg "Judgmints" to my basket...just because they were there (seriously, no judgmint please). Even if this section doesn't add significant dollars to your sales, it'll increase your UPT and, if you've done your buying strategically, boost margin.

How are you encouraging add-ons and upselling this holiday season? 

The most foolproof way to upsell? Knowing your customer inside and out.

Our powerful clienteling tools allow you to collect the customer data most relevant to your business and report on it any way you please. It's the first step to delivering a personalized customer experience that will keep them coming back again and again.

Watch a CRM Demo Video

Topics: Retail Tips & Techniques