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Get Ready for The Shopping Season with These 10+ Tips


We’ve heard it so many times it’s become a cliché: “The early bird catches the worm.”

For retailers, this old saying rings tried-and-true. After all, it’s never too early to get ready for the shopping season.

Holiday sales can represent anywhere between 20 and 30 percent of annual sales for retail businesses. While the Friday after Thanksgiving has been known as the unofficial start of the shopping season, 4 in 10 consumers begin holiday shopping before Halloween, and as much as 12.2 percent begin shopping before September.

Get Ready for The Shopping Season with These Tips - Statista

Preparing for the shopping season ahead of time can help e-commerce vendors and retailers of all industries convert more browsers into buyers, improve customer satisfaction levels, and dodge inconvenient (and avoidable) operational hassles.

Ready to put on your holiday best? Use these tips and best practices to make this year’s busy shopping season the most lucrative one yet.

1. Make Purchasing a Breeze

Holiday shopping isn’t easy – even the most timely, responsible buyers can get overwhelmed by the shopping season.

A difficult shopping experience during the holiday season can leave customers with a bad taste in their mouth – and businesses with a bad rap. Put the customer experience at the forefront of your priorities, and make purchasing a breeze by removing any friction from the buying experience.

Customers can experience many types of pain points, or common problems, while doing business with a company. This may include hard-to-navigate customer service channels, website problems, poor customer service, inaccurate product information, incorrect items being shipped, goods arriving damaged, items never arriving, and other inconveniences.

Remedy existing customer pain points before the holiday rush by considering the following:

a. Where do your customers currently experience friction in the buying experience? – Are there any common issues that happen before, during, or after checkout? Are there any reoccurring problems that customers are having with their orders? Tackling current pain points now will help keep simple, ongoing issues from snowballing during the holiday season.

b. What speed bumps have caused your customers undue stress during past holiday season(s)? – Were there any holiday-specific deals they had trouble applying? Did the flux of holiday traffic cause any problems in normally efficient processes? By bringing last year’s issues to mind, your team can take steps to keep the problems of the past from repeating themselves.

When considering these questions, be sure to collaborate with your customer service department, as they are the most familiar with customer pain points. Remember that for every customer who complains, 26 customers remain silent, meaning that the issues that customers complain about are likely happening a lot more often than you think.

Once you have tackled existing customer pain points consider: What could make your purchasing experience even easier? Consider offering guest checkout for shoppers who don’t want to make an account, and working to minimize steps and clicks before purchase. One way to do this is by adding single-page or one-click checkouts to your e-commerce website.

By exposing rough spots and making your online shopping experience even more convenient, purchasing will be easier – and smoother – than ever this holiday season.

2. Offer New Ways to Pay

Digital payments are gaining traction. A Paysafe study found that 31 percent of Americans are already turning to mobile walletsfor everyday use, while one in seven have used cryptocurrencies.

Paypal, a leading online payment platform, has over 237 million active users worldwide according to Statista. This and other digital payment methods such as Apple Pay, Google Wallet, and even Bitcoin have been attractive to consumers – particularly Millennials, the generation with the fastest growing spending power.

Wallet, and even Bitcoin have been attractive to consumers – particularly Millennials, the generation with the fastest growing spending power.

Digital payment methods can be faster, more secure, and easier for buyers to use than standard credit card forms. This helps increase buyer confidence, and push customers through checkout faster. Digital payment methods also help retailers address a more global, increasingly mobile customer base during the shopping season.

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3. It’s All About Shipping

Amazon has been pushing the boundaries of what is possible for e-commerce and changing customer expectations in the process. Competing with this e-commerce giant during the shopping season isn’t only about a frictionless checkout process: It’s also about providing fast, inexpensive shipping.

Unexpected or high shipping costs are listed as being the number one reason for shopping cart abandonment in the U.S. A separate report by Business Insider reveals that “A new study from L2 found that a quarter of shoppers would abandon a cart online if same-day shipping wasn’t available.”

In the report, BI Intelligence writes that same-day shipping is the key to e-commerce businesses successfully competing against Amazon, and that the gap between Amazon and other online realtors is smaller than one might think. According to the report, “Retailers could leapfrog Amazon by partnering with third-party delivery companies […] For example, Macy’s partnered with Deliv in 2015, which made same-day delivery available at only $5, compared with the $10 retailers charge on average — a move that may have helped solidify its spot as the second-largest online apparel retailer in 2016, just below Amazon.”

For smaller e-commerce vendors that may not have the resources to provide same-day delivery during the shopping season, free shipping offers can help satisfy early shoppers. By coupling free shipping with a small delivery window, you will be able to keep the holiday shoppers coming throughout the shopping season.

4. Loosen Up on Your Return and Exchange Policies

While it’s important to inspire buyer confidence all year round, during the shopping season this becomes even more critical. That’s because one of the reasons for buyer insecurity during the holiday season is that many shoppers aren’t buying products for themselves – they’re searching for something special for their friends and loved ones.

Give your customers peace of mind by enacting liberal return policies. There are many ways that your e-commerce business could make return policies more appealing for the holiday season. For example, many retail stores extend their 30-day return policy to 90-days during the shopping season. Others enact money-back guarantees to attract customers who might worry that purchasing the product will be a risk.

The following chart from Retail Dive shows how return policies might impact shopper behavior during the holiday season:

Get Ready for The Shopping Season with These Tips - Retail Dive

Source: Retail Dive

Generous return policies are an effective way to encourage early shopping, and to convince buyers to take the leap with your product. For e-commerce businesses, facilitating exchanges marks another big win.

Offering free return shipping is a great way to expedite both returns and exchanges. Gift receipts can also facilitate exchanges by empowering the recipient rather than the gift-giver to make the exchange. That way, new shoppers who are looking to exchange a holiday gift could wind up on your webpage for the first time, and even become loyal customers.

5. Put on Your Best Holiday Deals

Holiday offers and discounts are a great way to entice purchases during the shopping season.

According to a study by Inmar, 72 percent of coupons used in 2016 affected purchasing behavior, usually by encouraging shoppers to buy a product they otherwise would not have. During this study, 65 percent of shoppers said they would try a new product if they had a coupon for it and 58 percent would abandon their regular brand for a different one if the other brand offered a coupon.

Flash holiday deals can be used to generate sales during Black Friday, Small Business Saturday, and Cyber Monday. Super Saturday, or the last Saturday before Christmas, is a good way for companies with same-day or two-day shipping to push for last-minute holiday purchases.

With BOGO offers, small freebies, and discount bundles, customers can get a bonus treat for themselves while also gift-giving, or tackle holiday gifts for two people simultaneously. And remember: buyers who walk away feeling like they got a holiday steal are more likely to become repeat customers.

6. Serve Customers and Inspire Purchases Through Live Chat

With website traffic at its peak during the holiday season, it is important that e-commerce companies not miss a lead. Live chat provides businesses with valuable sales and customer service opportunities that aren’t possible through any other channel.

Recommended for you: 8 Ways that Live Chat is Boosting E-Commerce Sales (And What You Can Do to Get in On It)

During the holiday season, many contact centers experience high call volumes. This results in longer wait times and negatively impacts the customer experience. With live chat, agents can handle as many as three or more chats simultaneously (as opposed to one at a time over the phone). This helps businesses reduce wait times, and saves companies money on personnel costs and toll chargers.

Holiday shoppers are drawn to e-commerce for its convenience, and to live chat for the same reason. Like e-commerce, live chat can fit into any part of the user’s day during the busy holiday season. Customers appreciate the convenience of being able to use live chat without committing a large chunk of time and attention to the task. According to an Econsultancy report, 51 percent of customers prefer live chat for multitasking purposes, while another 21 percent prefer live chat so they can shop while they work.

Recommended for you: Top 10 Live Chat Benefits You Have to Know

Live chat also increases sales. A study by the American Marketing Association shows that live chat can increase conversions by at least 20 percent and that the typical ROI rate from paid live chat software for sales teams is about 300 percent. The same report states that customers that use live chat are three times more likely to make purchases versus those who don’t. This can have a huge impact on the number of browsers your business converts into buyers during the holiday season.

7. Plan Specific Marketing Action

According to LoyaltyOne, more than two-thirds of consumers strongly agree that companies, retailers, or brands send them too much irrelevant communication. During the holiday season, smart, targeted marketing (rather than an onslaught of messages) is the key to a successful advertising experience.

E-commerce companies with live chat can use the visitor segmentation feature to divide their website visitors into different segments based on pre-defined rules. This allows them to target leads based on factors such as geographical location, browsing behavior, referral page, and more. E-commerce businesses can then set automated proactive chat messages to engage website visitors with personalized content directly on their webpage.

Recommended for you: Visitor Segmentation in Comm100

Other specific marketing actions to consider are email campaigns, social media publications, in-app push notifications, and paid advertisements. Fifty-nine percent of consumers report using loyalty rewards when holiday shopping, meaning that setting up a loyalty program with reward redemption reminders can be an effective marketing strategy for the shopping season.

For any marketing campaign, plan ahead: you don’t want your team to struggle to create banners or send out newsletters last minute. Communicate your marketing strategies between departments for effective planning and implementation. For example, if your marketing department emails out a promotion, make sure that customer service knows, so that if a customer calls in about a non-functional promotional code, your agents will know whether that code is real or is from a non-affiliated third party.

8. Know Your Competition

Marshal Cohen, chief industry advisor of The NPD Group, says that the holiday season isn’t about getting more customer dollars. “Customers don’t have more dollars,” Cohen says. “If there’s going to be any growth, it’s going to come at the expense of somebody else.”

To win your customers’ hearts – and what’s in their wallets – it’s important that you know your competition, and take steps to offer your customers the best bang for their buck. Get informed on what your competition does right during the holiday season, and get on board. Consider offering better prices, discounts, product variety, customer service options, shipping options, or return policies than your competition in order to get a leg up. Offering a charitable gift with each purchase can also help rally buyers behind your business instead of the competition.

9. Encourage Research

Comparison shopping is a staple of the holiday season, and the internet makes comparison shopping even easier. Get ready for well-informed, well-researched buyers, and appeal to your consumers’ desire to be empowered through knowledge.

According to the National Retail Federation (NRF), retailers who are preparing for the shopping season should “be research-ready by October” and work to encourage and assist customers with their holiday research. This can be done by making product details and information easily locatable online and on mobile apps, as well as by sending out content or buying guides.

10. Offer Shareable Wish Lists

For e-commerce, discoverability during the holiday season isn’t quite as easy as it is in-store. Unlike in shopping malls, where consumers might wander into a store that they have never been in based on an attractive holiday window display, many customers need to be referred to e-commerce websites.

Let your loyal buyers tell their friends and family which of your products they loved by offering shareable wish lists. Wish lists can facilitate the holiday shopping process for buyers, and take the guesswork out of shopping for loved ones. In a survey of over 2000 holiday shoppers, the NRF found that over 60 percent of consumers would like to use more online wish lists in the future.

11. Organize Your Inventory

What good is a wish list if the items listed are out of stock?

Remember that customers begin their holiday research early – more than half of seasonal shoppers begin researching products in or before October. In order to satisfy customer demand, you will need to forecast the right amount of inventory for the influx of product orders.

Note what supplies and products you will need to have in stock during the shopping season. Consider how your popular items are currently selling, and what items – if any – ran out last holiday season. This will help you make an informed estimate of how much of each product to order from your supplier before the holiday rush.

Make sure that your inventory is well-organized, and that your warehouse has a clean and efficient layout. Ensure that your warehouse software is up to date, and that any automated processes are functioning smoothly.

12. Enable and Encourage Self-Service

There are many ways that e-commerce companies can use self-service to their advantage during the shopping season.

Self-service takes the pressure off of busy customer service channels, and empowers customers to get answers to their questions and complete processes without help.

To optimize your self-service offerings, start by updating your knowledge base with information that is current and relevant to the holiday season. Make sure that your knowledge base is easy to find, and that is well organized so that it doesn’t leave customers in doubt.

Another self-service tool to consider for the holiday season is chatbots. Chatbots are automation systems that can act as evolved self-service portals or advanced knowledge bases on e-commerce websites. Businesses can program chatbots to answer commonly asked questions, freeing agents up to take care of more complex issues. Chatbots cost as little as the price of maintaining a single live chat agent, and are available to assist customers 24 hours a day, 7 days a week.

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E-commerce businesses can also encourage customers to assist one another by leaving reviews and feedback. This way, customers can share their experience with the product, post photos, and help clear doubts by answering questions that potential buyers might have.

13. Manage Your Social Media

Customers prefer different channels for reaching out to companies. Keep your social media strategy sharp during the holiday season, and be open to serving customers on this popular channel.

Recommended for you: 9 Unmissable Reasons Why You Need to Care about Social Media Customer Service

For the best results, make sure your social media department is co-owned with customer service. This is especially important during the holiday season, as directing customers who are contacting you on social media to call customer support to resolve an issue further clogs service lines, and can upset rather than help customers.

Recommended for you: You Need a Jointly Owned Social Media Customer Service Strategy ASAP – Here’s Why

14. Quality Check: How’s Your Website?

Before the shopping season hits, make sure that your website is running smoothly. Expect heavier website traffic during the holiday season, and ensure that your site is ready to accommodate this.

Your website should also be accessible and fully navigable from all devices during the holiday season, including mobile and tablets. Mobile shopping is on the rise, and over half of all visits to e-commerce sites – 54 percent – are coming from smartphones and tablets.

To ensure the best browsing experience for your website visitors, it is also important that your content is displayed in an attractive, comprehensive manner. Have top selling products visible first, and ensure that your live chat window is properly sized so that it helps the shopping experience and does not block or hide any content. Make sure that your website has tools – such as “you may also like,” suggestions – to help shoppers find their way to the right product.

With your website technically sound and easily navigable, you will be ready to meet holiday traffic.

15. Staff Up!

It’s common for retailers to hire seasonal staff during peak shopping seasons. Consider hiring seasonal customer service agents to help your e-commerce business meet the holiday boom. This could include in-house customer service representatives, or remote live chat agents.

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Look to hire agents a few months before the shopping season hits, and begin onboarding them early. That way, your seasonal agents will be a capable part of your team by the time holiday shopping picks up.

Don’t forget to use live chat reporting to optimize workflow. Live chat reports can help you decide how many agents you need to effectively cover different timeframes, and can ensure that you have the right number of agents working during peak contact hours.

16. Take Care of Your Employees – And Yourself

The holiday shopping season can be a time of great gains for e-commerce businesses. However, it is also a time when teams are under a lot of pressure.

Help keep your staff motivated by showing that you care about them and their well-being. Consider treating the office to breakfast or lunch during a busy week. You may even consider using games, activities, and prizes to help employees reduce stress during their breaks.

Recommended for you: The Art of Boosting Team Morale: How to Motivate Your Live Chat Team

By taking care of your employees during the shopping season, you will be able to increase customer satisfaction, improve efficiency, and reduce employee turnover rates.

In the midst of caring for your customers and your employees, don’t forget to take care of yourself! Practice small acts of kindness to yourself throughout the shopping season, and remember – you deserve it!


As NRF President and CEO Matthew Shay said at the end of last holiday season: “Retail has proven once again that it is the most nimble industry in the economy, able to transform and reinvent itself to meet always-changing consumer demands. Retail today doesn’t look like retail 10 years ago and it certainly won’t look the same in another 10 years. But retail is retail, and will always be here to serve its customers.”

By brainstorming ideas for how to best handle the shopping season before it hits, you will be able to optimize processes, sail past your competition, and turn customer interactions into memorable moments, even during the busiest time of year.

For more information, check out our blog post, Everything You Need to Know about Seasonal Hiring for Live Chat.

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Isabella Steele

About Isabella Steele

Isabella is a freelance editor, writer, and blogger with Comm100. She is passionate about helping people, teams, and organizations grow into their full potential, and excel in their service. In her spare time, you can find her traveling, painting, or drinking copious amounts of coconut water. Connect with Isabella on LinkedIn.