How Square Sellers Are Preparing for the Holidays

hoiday seller preparations

The holiday season is upon us, and it’s going to be a big one. To prepare, you may need to increase inventory, hire seasonal help, decorate, wrap gifts, ship orders, advertise holiday specials…

You get the picture — there’s a lot to focus on.

We chatted with some of our favorite Square retailers across the U.S. to see how they prepped for the 2018 holiday season — from custom orders to payroll and holiday pop-up shops — and how their experiences can help you prepare for spirited shopping.

We want to hear from you

Submit your own Square seller story

Get Started

Laura Lemon, owner of Lemon Laine in Nashville, TN, and Houston, TX

Laura grew up with a love for makeup and beauty. “From making lip balms for my friends in middle school to being a self-taught makeup artist who landed my first job at Saks Fifth Avenue, I fell in love with the magic of makeup and the confidence it can give women,” she says.

After 15 years in various beauty roles, Laura opened Lemon Laine. “Plain and simple — I felt like there wasn’t an authentic beauty shopping experience out there,” she says. “I thought women deserved better — a place that they could trust, while being approachable, personalized, and honest. Cue, Lemon Laine.”

lemon laine retail location

Photo by Caroline Sharpnack

Your favorite product?
Pai Rosehip Oil.

Your customers’ favorite product?
Honest Hazel Eye Masks.

How do you differentiate yourself in the market?
Through our staff’s expertise and product knowledge, and the one-of-a-kind experience you receive when you walk through our doors.

What are you doing to prepare for the holidays?
Inventory! I have one season under my belt so it’s been great to review my sales history and make sure I’m stocked up on the items that sold last year, while also placing bets on some new and exciting items.

What are some of the biggest challenges or adversities you’ve faced in running your business during the holidays?
Staffing. My payroll was too high, too early. Holiday inventory hit our shelves by early November but the traffic didn’t really pick up until December.

Ian VanDam, owner of Civil Alchemy in St. Louis, MO

Civil Alchemy was created to house ideas and beloved items. “Like the corner stores, general stores, and outfitters of yesteryear, we wanted to reconnect retail with physical spaces in an age of increasingly digital commerce,” Ian says.

civil alchemy

Your favorite product?
Our Truly Floral Blue Gin. We worked on developing it for about a year and launched it exclusively in the store in June. The response has been great thus far, and we’re currently working on our next one — Truly Floral Pink.

Your customers’ favorite product?
The Swedish rain jacket company, Stutterheim, has been a huge hit in every season this year. We can’t keep them on the shelves!

How do you differentiate yourself in the market?
We try to let our customers tell their own story, using our products, something often overlooked in the retail sector. Simply put, we carry things we truly like, instead of being just an apparel boutique, or just a liquor store.

You can see this through all the categories we carry at the store, whether it is fresh flowers, tools, apparel, or a six-pack of beer; our products are unified by form and functionality rather than strict genres.

What are you doing to prepare for the holidays?
Lots of buying! Promoting events, social media marketing, and some print media. We even published a lookbook for the holiday shopping season. It includes apparel from some of our favorite brands, as well as jewelry and accessories from our in-house Civil Alchemy Brand.

What are some of the biggest challenges or adversities you’ve faced in running your business during the holidays?
Because we’re so new (we’ve only been open for one holiday season), it is difficult to forecast how much product we need to order to meet consumer demands, or how many people we will need staffed on any given day.

Kenya Brantley, owner of Greenhouse Mercantile in Newnan, GA

Kenya started Greenhouse Mercantile as a gathering place that celebrated local makers. “I wanted it to be somewhere you could go to find products that you can buy and be proud of,” she says. “This was created to be a space that’s a sanctuary for people that seek out the un-ordinary.”

greenhouse mercantile

Your favorite product?
Our locally made baby bonnets by PLAi Handmade — I have a nine-month-old and their bonnets are absolutely adorable.

Your customers’ favorite product?
Definitely our locally roasted Savage Boys coffee — yum!

How do you differentiate yourself in the market?
We strive to be different by making sure that each and every item is a part of our vision. Every product is a part of our curated look and feel for the store. We work to ensure that our goods are fair trade and locally or American-made.

What are you doing to prepare for the holidays?
Preparation includes making sure that we have gift items available for all our customers. Social media ads are also a huge part of our holiday marketing strategy.

We have a year-round pop-up shop space, where we host a variety of creators and makers, that’s filling up fast for the season. Finally — participation in Black Friday and Small Business Saturday are two of the highlights of our year!

What are some of the biggest challenges or adversities you’ve faced in running your business during the holidays?
Here in Georgia, sometimes our “winters” can be pretty warm. Often, customers find it hard to get into the Christmas spirit, so we try to offer more year-round gift items, like books and specialty foods.

Becky Miller, owner of Modern Nomad Home in Denver, CO

Inspired by NYC’s ABC Carpet & Home, Becky brought a taste of the shopping experience to Denver with a shared 5,500-square-foot warehouse. “We’ve created an interactive shopping experience with like-minded vendors,” she says. Currently, nine vendors make up Modern Nomad Denver, with goods from around the world.

modern nomad

Your favorite product?
My favorite item in the shop is currently our large-scale light pendants from Ay Illuminate.

Your customers’ favorite product?
We sell a lot of jewelry from small artists and makers from around the world.

What are you doing to prepare for the holidays?
We are ordering and stocking up on what we know are big sellers, i.e., books, candles, jewelry, and will be hiring seasonal help to give shoppers a more personal experience.

What are some of the biggest challenges or adversities you’ve faced in running your business during the holidays?
The holidays are a crazy time in the retail world — and I think it’s that movement to bring people back out to shop and support small businesses instead of shopping online from your desk at work.

Elizabeth Plotz, owner of South Shore Vintage in Patchogue Village, NY

Elizabeth dipped her toe into vintage selling online part-time while working a full-time job. “Business took off. I would have customers come to pick up purchases from my storage space — which was actually a space in an office building — and they would look around and shop while there,” she says.

Based in a town that has undergone a bit of a revitalization in the past decade, Elizabeth saw a need for more stores to shop in. “I saw a great need for more retail stores in Patchogue Village, so I found a centuries-old home to house South Shore Vintage,” she says.

south shore vintage

Your favorite product?
It’s tough to decide, since I handpick all the items that come into the shop. It’s all pieces that I love and would put in my own home.

I tend to gravitate toward vintage kitchenware. I love anything that is as functional as it is beautiful. I’ve got some fantastic vintage copper tea pots and cookware in the shop right now that I just love.

Your customers’ favorite product?
My customers love the large selection of vintage clothing — I can’t keep vintage denim jeans in stock.

How do you differentiate yourself in the market?
We’re different because of the way we merchandise, present, and market our products. I’ve been in so many antique and vintage shops where the shelves are packed to the brim and overloaded to the point where you can’t really see everything and feel like you’ll break something if you touch anything.

My shop is pared down to only the best-quality items, displayed in a way where you can see each individual item on the shelf, or browse through the racks of clothing with ease.

I’m also very active on social media and carefully curate my shop and products on Instagram to tell the story of the shop through photos — some similar shops in my area don’t have any social media accounts.

Plus I’ve embraced technology in my shop. As much as I would have loved to use an antique cash register in my store, the Square POS has been invaluable in helping me run my business. I especially love how I can use it on my phone through the app — vital when I’m a vendor at outdoor markets, and crucial for me to keep track of employee sales during the day when I am not in the shop.

What are you doing to prepare for the holidays?
I’m gearing up for the holiday season by stocking up on holiday merchandise and giftable items for the shop. I’ll be doing some marketing via social media starting next month and plan on having a few sales during the season, starting with Black Friday and Small Business Saturday.

What are some of the biggest challenges or adversities you’ve faced in running your business during the holidays?
The biggest challenge for me specifically is keeping the shop fully stocked during the holidays. I’ve learned to adjust by starting to shop for holiday merchandise earlier in the year.

Yvette Jenkins of Love Travels Imports in Detroit, MI

During a life change, Yvette wanted to do something that would make an impact for women artisans, especially women in disadvantaged communities. “I was inspired by the beauty of some unique and innovative handmade handbags made in South Africa, and wanted to share them with everyone,” she says. Today, Love Travels Imports has both an online and a brick-and-mortar presence in Detroit.

love travels imports

Your favorite product?
The Mielie bags from South Africa.

Your customers’ favorite product?
This year there’ve been two favorites: the hand-felted unicorn pencil covers and the hand-painted scarves from Haiti.

How do you differentiate yourself in the market?
Our relationships with our artisans and our clients. We listen to them and connect with them by sharing their stories. We go the extra mile to make our customers happy. We’ll even have products custom-made for them.

What are you doing to prepare for the holidays?
Marketing: sharing via our blog and newsletter. Bringing in some new, fresh artisan-made collections. Stocking up on long-time favorites like our metal angels from Haiti.

What are some of the biggest challenges or adversities you’ve faced in running your business during the holidays?
In Michigan, the biggest challenge has been the unpredictable weather. To combat that, we’re working on driving more online traffic.

Also, we offer customers more personalized and small-batch custom ordering options earlier in the season. Several people started their holiday shopping in August and September. We deliver those orders in November and December.

Related Articles
Hero Merchants: How Veterans Run Their Businesses
Square + ☕️☕️☕️ = ❤️
Here are 7 Businesses that Cater to Our Furry Friends

Accept chip cards and Apple Pay everywhere.

From magstripe and chip cards to NFC payments, accept every way your customers want to pay.

Get started

Learn More

Get the latest business tips and advice delivered straight to your inbox.

Each issue will feature articles and advice on how to grow sales, improve your marketing, simplify accounting, and much more.