Holiday Retail Prep: Your Comprehensive Guide to a Successful Season

Picture the holiday season: twinkling lights, delicious seasonal treats, and a sense of peace and joy that only comes with the cold weather. 

As a small business owner, that description probably doesn’t quite ring true to your experience during the months leading up to the holidays. 

The holiday season is a key time for retailers, bringing opportunities to boost your bottom line — but it also brings along unique challenges and strains. 

We know that the holiday retail season is a delicate balance between stress and success, which is why we’ve put together our best tips and advice to help you plan profitable sales, implement effective marketing efforts, and provide stellar customer service. 

In this guide, we’ll cover:

  • The peaks of the holiday retail season
  • Why it’s important to plan your holiday strategy early
  • How to prepare your retail inventory management process and store layout for the holiday rush
  • How to use e-commerce and BOPIS to boost sales and increase customer satisfaction
  • Inspiration for your Black Friday, Cyber Monday, and Small Business Saturday sales
  • Strategies to avoid the post-holiday slump and boost customer loyalty
  • How to use your POS system to keep your store running smoothly throughout the holiday season

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    The Holiday Retail Season at a Glance

    During the holiday retail season, customers are browsing for thoughtful gifts for their loved ones, stocking up on festive decor and other seasonal goodies, and purchasing everything they need for holiday parties and feasts. Along with these items, they’re also looking for great deals! Customers are willing to spend more during the months leading up to the holidays — but that also means that they’re on the hunt for the lowest prices and most enticing sales. 

    Most shoppers purchase their gifts and holiday essentials in November and December, but holiday shopping starts earlier and earlier each year. Many customers start looking for the perfect gifts (and perfect prices) as soon as September! 

    Your store should be at the top of its game in terms of staffing, inventory, and marketing throughout these months, but here’s an overview of the season’s major shopping peaks: 

    • Black Friday and Cyber Monday: Black Friday is the day after Thanksgiving, and it’s typically when retailers run their biggest sales of the year. Your customers plan to spend big and save big on Black Friday. Cyber Monday takes place on the Monday after Thanksgiving and is e-commerce-focused, with customers searching for deals from the comfort of home. We’ve listed Black Friday and Cyber Monday together because many retailers treat this as a multi-day opportunity to offer their best discounts.
    • Small Business Saturday: Small Business Saturday is a shoppingholiday that occurs on the Saturday after Thanksgiving. Small Business Saturday began as a way to encourage consumers to shop small and rely on local businesses for all their holiday needs. This is a great opportunity to generate buzz for your small business, make huge sales, and create connections with your community. comcash-holiday-infog

    To make the most of the busiest retail season of the year, set aside some time to plan. What kinds of discounts and deals do you plan to run for Black Friday, Cyber Monday, and Small Business Saturday? How are you going to ramp up your marketing strategy in the months of November and December? Are your inventory management, staffing, and checkout processes ready for high-volume shopping days?

    Answering these questions will put you on the path to your most successful holiday retail season yet! 

    Get Your Store Ready for the Holiday Retail Rush

    Prepping for the holiday rush might seem like a daunting task, but we’ve broken it down into a list of manageable to-dos. 

    Start Early

    It’s never too soon to start your holiday season prep. Customers start their shopping earlier and earlier every year — which means your store needs to be ready! 

    Before you start making a plan, think back to your past few holiday seasons. What were your store’s wins? What could have gone better? What do you wish you had done to prepare? 

    Reflecting on the success of previous holiday shopping seasons will help you set priorities for this year. For example, if you found yourself frequently running out of stock of popular items, you’ll want to up your inventory management game. If you struggled to attract new customers to your store, that’s a sign to invest in your marketing efforts. If you and your employees had a difficult time keeping up on your busiest shopping days, you’ll need to speed up your checkout process. 

    Setting goals, planning out your promotions, and preparing your store early will enable you to spend more time with your customers and less time solving problems this holiday season.

    Manage Inventory Effectively

    If you don’t have a seamless inventory management process in place now, it’s time to implement one. Inventory management is always a key component for retail success, but it becomes even more crucial during the holiday season. 

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    Your customers rely on your small business to help them find the perfect gift, and if your store isn’t well-stocked, they might not be able to find everything on their list.

    For stress-free inventory management, lean on your store’s point of sale system. Your POS system tracks your stock from the moment it arrives at your store to the minute a customer purchases it, allowing you to conveniently see exactly what you have in stock at any given time. Equipped with real-time updates about your inventory, you’ll be able to keep your store well-stocked during the holiday season and beyond. 

    An added benefit of relying on your POS system for inventory management is that you can explore historical data about your stock. For example, knowing which items previously sold the most and the least will help you make more informed stocking and promotional decisions for the upcoming holiday retail season. 

    Create Enticing Merchandise Displays

    Eye-catching displays will delight your customers when they visit your store, making shopping at your small business an exciting, welcoming experience. In the months leading up to the holidays, it’s critical to emphasize your most giftable products, and to make sure your customers are aware of your current promotions. 

    Here are a few tips: 

    • Decorate your store. If you embrace the holiday spirit, your customers will, too! Make shopping in your small business fun to encourage shoppers to spend more time browsing everything your store has to offer. 
    • Utilize your highest traffic areas. Create visually appealing displays near the entrance of your store with your most popular items. 
    • Highlight gifts. Use bright, colorful signage to emphasize items that would make great presents. You might also consider creating baskets combining some of your bestselling gifts.
    • Create window displays. If your store has a window, a brightly-colored, holiday-themed display can entice customers to come inside. 
    • Make it interactive. Choose a few of your best holiday items to allow customers to interact with or sample. This works best with items like toys, cosmetics, or even edible goodies. 
    • Keep it fresh. Regularly straighten up your display, and change it up a few times throughout the season to create a consistent and memorable experience for each of your customers, whether they’re loyal shoppers or visiting for the first time. 

    Leverage E-Commerce

    Many holiday shoppers prefer to browse for gifts from the comfort of home. When creating your holiday retail plan, make sure you’re considering these customers as well. 

    If you don’t have an online store, the holiday season is the perfect time to launch one. Your customers will love the convenience of being able to shop from home — and you’ll love the extra sales you make from having an e-commerce platform. 

    For the easiest possible experience, choose a POS system with an integrated webstore that allows you to seamlessly sync your online and in-store inventory and sales. Make sure that you’re offering discounts and deals to boost your online sales throughout the holidays!

    Utilize BOPIS

    Buy online, pick up in-store — or BOPIS — is an increasingly popular way to shop. During the busy holiday retail season, many customers simply don’t have the time to browse your store, pick out their items, and wait in the checkout line. BOPIS is an excellent way to provide a convenient option for them and to boost your sales. 

    To take advantage of BOPIS, make sure your store’s POS system and employees are up to the task. You’ll need to enable BOPIS on your business’ e-commerce platform, and spend some time training your team to efficiently fulfill online orders. While it might take a little extra effort, your customers will appreciate how easy it is to check off their shopping lists at your small business. 

    Craft a Winning Marketing Strategy

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    Whether you’ve just opened your store or you’re a seasoned retailer, marketing is a critical component of a successful holiday shopping season. An effective holiday marketing strategy can help you attract new customers to your store and boost your holiday sales.

    Your marketing focus during the holiday retail season should be to let customers know that your store is the go-to place for the best gifts and the best deals. Here are a few strategies for generating buzz before the holiday rush. 

    Utilize Email Marketing

    Email is a great way to stay in touch with your customers as the holidays approach. To help you take advantage of this strategy, we’ve outlined a few ways to boost your sales and bring customers through your door during the holiday shopping season: 

    1. Send emails regularly. Toward the beginning of the holiday retail season, take the time to plan out an email calendar, and ensure you’re regularly connecting with your customers to share upcoming promotions, new items, and gift ideas. 
    2. Create a gift guide. Inspire your customers to find the perfect gifts for their friends and family at your small business by sending gift ideas and highlighting your bestselling items. 
    3. Segment your audience. Using historical sales data, you can create segmented lists of your customers and send them more personalized emails based on their previous purchases. Taking the extra time to add a personal touch can make a big difference in your sales numbers. 

    Email marketing doesn’t have to be time-consuming; your POS system should have email integration options that make it easy to segment your audience and schedule emails to help you stay connected with your customers. 

    If you’re looking for a quicker, more concise way to communicate with your customers, check to see if your POS system offers an SMS messaging integration. You’ll have fewer characters to work with, but SMS messaging is a great way to update your customers on your sales and new arrivals. 

    Leverage Social Media

    Social media is another great way to build excitement during the holiday retail season. With social media, you can easily update your customers when new arrivals hit your shelves and when you’re offering your best deals. 

    Especially around Small Business Saturday, social media is a great opportunity to create meaningful connections with your customers and community. You can use this platform to share your small business story, inform your customers about your mission, and highlight what sets your store apart from the competition. 

    Create Exciting Promotions

    During the holiday retail season, your shoppers are on the hunt for the best prices — and they expect your store to deliver. Here are a few promotional ideas to help you generate excitement and sales for your small business during the holidays: 

    1. Mix and match promotions allow you to offer customers special pricing when they buy a certain combination of items. This is a great promotion for the gift-giving season! For example, you can combine two commonly gifted items together and offer a special price for both — helping your customers build the perfect present and save big. 
    2. Buy one, get one (BOGO) deals are always a hit with customers. They’ll feel like they’re getting a great discount, but they’re also more likely to spend more than they originally planned. 
    3. Hourly or daily sales are a great way to create excitement and urgency, especially around peak shopping days like Black Friday. With time-sensitive promotions, you can offer customers significant discounts on certain items or categories of items, encouraging them to spend more and to visit your store more often. 

    You may also want to consider offering exclusive deals to your customer loyalty program members. These shoppers are already invested in your brand and willing to shop at your small business, and offering them special incentives during the holiday season can boost your sales even further. 

    For example, you can offer bonus rewards points, exclusive insider discounts, or even free gifts to loyalty program members to encourage them to shop at your store this holiday season. 

    Deliver Excellent Customer Service

    The holiday retail season is a crucial time to create a memorable experience for your customers. Exceptional service during this period is not only a sales booster, but also a way to nurture loyal shoppers who will continue to support your small business after the holidays. Here are a few tips for boosting customer satisfaction during these busy holiday months. comcash-holiday-service

    Prioritize Training Your Team

    From your newest staff members to employees who have worked in your store for years, everyone on your team could use a refresher before the holiday retail season. 

    This is the perfect time to make sure that your team feels completely confident using your store’s POS system to clock in, manage inventory, look up items for customers, and process transactions efficiently. 

    Along with covering your store’s processes, you’ll also want to share some tips for providing top-notch customer service during the holidays. Tell your team why the holiday season is so important for small businesses like yours, and inspire them to surprise and delight customers with service that goes above and beyond. 

    Prioritizing time for training before holiday shopping ramps up will ensure that everyone on your team is on the same page about how to create the best possible experience for your shoppers. 

    Work on Your Holiday Schedule Early

    The holiday season is one of the toughest times to keep your store well-staffed. Many of your employees may need specific days off, and they’ll also want to know their work schedule as early as possible so that they can make their holiday plans. 

    To keep your store running smoothly and your customers happy, try to put together your holiday staffing schedule as early as possible. Send a survey to your employees asking about their scheduling preferences and conflicts early on in the season so that everyone can be prepared. 

    If you’re expecting a particularly busy holiday season, you may even consider bringing on additional staff to fill in the gaps. 

    Leverage Your POS System for a Successful Season

    ​​Your point of sale system is the most important member of your team during the holiday retail season. Throughout these bustling shopping days, you’ll need to lean on your POS system to keep your store well-stocked, your checkout lines short, and your customers happy. 

    Your POS system also provides valuable insights into your sales trends, helping you identify peak shopping periods and optimize your operations.

    Here are a few key features that your POS system should have to keep your store running smoothly throughout the holiday rush: 

    1. Inventory Management: During the holidays, a well-stocked store is paramount, but increased foot traffic and higher customer service demands mean that you’ll have less time than usual to keep an eye on your stock. Luckily, your POS is fully capable of handling inventory management. Your POS system should update automatically when new stock arrives and when a customer makes a purchase, ensuring that you always have access to an up-to-date record of your stock.
    2. Sales Reporting: The holiday retail season is a time to stay flexible and adaptable. Your POS system can help you adjust your strategies to boost your sales and keep your store running more efficiently by highlighting your busiest hours, bestselling items, and more. Historical sales reports can also help you in the early stages of holiday planning by showing you what worked well and what could have been better during previous holiday seasons. 
    3. Customer Loyalty: The holiday season is a pivotal point for your relationship with your customers, offering opportunities to build loyalty and generate repeat business. A POS system with a built-in customer loyalty program can help you offer exciting rewards for your customers to encourage them to return to your small business again and again. As a bonus, your POS system will also provide insights into your most loyal customers’ shopping habits and favorite items, helping you tailor your holiday offerings to exactly what they want. 
    4. Multiple Payment Options: During the holiday season, your customers are in a hurry to complete their shopping. Accepting multiple payment types including cash, card, contactless, and mobile pay will create the quickest and most convenient experience for them. Don’t forget about gift cards! Your customers will want to purchase gift cards for those friends and family members who are difficult to shop for, so make sure your POS system and staff are ready to efficiently process gift card sales. 

    Before the holiday rush ramps up, make sure your store’s POS system is ready and has all the tools you need to keep your store operating at its best.

    Keep the Sales Going After the Holidays

    While the holiday retail season is a fantastic sales opportunity for your small business, don’t let things slow down as you head into the new year. Having a solid post-holiday strategy can help you maintain sales momentum, manage returns and exchanges efficiently, and set the stage for continued growth. 

    Here are a few tips and ideas for helping your store thrive in the post-holiday season: 

    1. Plan Post-Holiday Sales: Whether it’s before or after the holidays, all customers love a good sale. Planning promotions after the rush can help you turn over extra inventory and avoid the post-holiday slump. If your store has leftover holiday-themed goodies and decorations, consider selling them for a steep discount to help customers prep early for next year’s festivities. Another fun promotional idea is to offer customers a deal on gifts for themselves, encouraging them to cross off items on their gift lists that they didn’t receive.  
    2. Capitalize on Customer Loyalty: The post-holiday season is the perfect time to turn your one-time holiday shoppers into loyal fans of your small business. To keep these customers coming back, consider offering special perks through your customer loyalty program like bonus loyalty points or even a special gift for spending a certain amount at your store. 
    3. Offer Easy Returns and Exchanges: The end of the gift-giving season means more returns and exchanges than usual. To ensure that your customers get exactly what they want, consider extending your return and exchange windows before and after the holidays. An additional benefit of a generous policy is that many many customers who visit your store for a return or exchange are likely to make a purchase. It’s a win-win!

    These strategies will help your small business avoid a dip in sales after the holidays and will give you a great foundation for success as you head into the new year. 

    Get Your Small Business Holiday-Ready

    The holiday retail season is a time of considerable opportunity for your small business, from breaking your sales records to nurturing customer relationships that will last long after the holidays. But for holiday success, you need the right tools, processes, and planning in place. 

    Since we covered so much throughout this guide, we thought it might be helpful to sum up some of our top tips for holiday retail success:

    • Start your planning as early as possible.
    • Plan enticing sales for Black Friday, Cyber Monday, and Small Business Saturday.
    • Level up your marketing game with social media, email, and SMS marketing.
    • Utilize e-commerce for a boost in your sales.
    • Leverage your POS system to save you time on inventory tracking, team management, sales recording, promotional scheduling, and more.
      Planning for your best holiday retail season yet might seem intimidating, but we’re here to help every step of the way. 

    Planning for your best holiday retail season yet might seem intimidating, but we’re here to help every step of the way. Schedule a personalized demo with one of our retail industry experts to learn how Comcash can help your small business thrive during the holidays and beyond.