Running A Business

The 2020 Guide to Nailing Online Sales This Holiday Season

Nov 20, 2020 • 10+ min read
Man Checking Sales
Table of Contents

      You thought last year’s holiday season was intense? Well, unless you’ve been hiding under a rock for the last 8 months (which doesn’t sound like a bad idea right now), then you know to expect the unexpected in 2020.

      Regardless of what happens this holiday season, it’s clear we’re not going to see good ol’ mile-long lines, door-busting sales (good riddance), or pre-Black Friday campouts. In fact, many major retailers plan to keep their doors closed on Thanksgiving Day. Target even kickstarted their Black Friday sales in October to “stretch out the savings” and the crowds.

      Black Friday was already transforming into Cyber Friday, and now it looks destined to become Cyber November.

      However, small businesses need this holiday season. According to VISA, nearly 70% of small businesses see the winter holiday as the most important sales opportunity for their businesses. COVID-19 put a real damper on summer sales, and companies must now fight until December 31 to hopefully turn a profit (or at least marginalize their losses).

      “It can’t be exaggerated how important it is,” says Jeff Rosenblum, cofounder of digital marketing agency Questus. “In just a few days, many brands and small businesses can sell as much as they do the rest of the year combined.”

      Salesforce predicts online sales will grow by 30% this year, while 60% of Americans plan to do the majority of their shopping with local businesses—that sounds like a delicious recipe for small business success.

      Small businesses must adapt to 2020’s demands to succeed this holiday season, and that means going digital. Fail to nail your online sales and you’re bound to dig deeper and deeper into the black hole of 2020. Get it right, and you could waltz into the new year with a happy, healthy business.

      Let’s teach you how to dance digitally.

      Prepare Now—The Holidays Are Already Upon You

      Man preparing packages for online business


      A survey from Voxware found that 51% of consumers plan on starting their holiday shopping earlier than normal this year, and 76% intend to purchase more than half of their gifts online. 

      While it’d be best to have your digital sales up and running yesterday, today’s better late than never.

      First things first: you need to get your business online. If you’re already there, then breathe a quick sigh of relief and prepare for the next steps. If you’re not online yet, don’t panic.

      Check out Your All-in-One Guide to Taking Your Business Online for a quick walk-through on how to go digital with your business. It’ll provide you with the details of creating a website, building out social media profiles, planning email marketing campaigns, and more.

      Got it? Good.

      With your online presence established, it’s time to optimize for the holiday season.

      Plan Your Holiday Communications

      Now’s the time to overcommunicate rather than undercommunicate. Yes, your customers’ social media feeds and email inboxes will likely flood with messages—but they’d rather get up-to-date notifications on delivery expectations than silence.

      Use your website, social media profiles, email program, and more to keep customers in the know:

      • What deals can they expect this holiday season?
      • Will there be any expected shipping delays?
      • What’s the cutoff date for shipping by Christmas?
      • Are there any products you anticipate will sell out quickly?
      • Where can customers find your deals? Your website, Amazon, retailers?

      Don’t leave it up to guesswork—give your customers all the FAQs and answers they need.

      Brace for Impact

      Anticipate demand before it knocks down your business. Cash flow forecasts will help, but plan for the worst so you’re not caught off guard.

      • Website: Make sure your website’s ready to handle a jump in traffic. The last thing you want is a site crash on Black Friday.
      • Stock up on inventory: Don’t miss out on sales by understocking products—plan for adequate inventory.
      • Hire extra help: Prioritizing online sales doesn’t mean you’ll need less help. There are still customers to serve, orders to fulfill, and sales to make—make sure you’re staffed appropriately.
      • Budget for increased marketing: It takes money to make money. If you want more digital sales, plan on more digital spend. If money is tight, consider getting a business line of credit to expand your working capital.
      • Upgrade your email account: Avoid unnecessary overages by estimating your email volume in advance. If your email volume (marketing emails, shipping notifications, support, etc.) is set to skyrocket this holiday season, consider upgrading your account in advance.

      Add Curbside Services

      As of August, close to 75% of the top 50 store-based retailers in the US offered curbside pickup. Consumers still love to shop in person, even if they only get to make it to the curb—and that’s why digital sales coupled with curbside pickup is a winning combo in 2020.

      “Americans are used to their cars and actually do like stores, so this is kind of a hybrid where you’re getting the best of both worlds,” said Oliver Chen, a retail analyst at Cowen.

      Curbside pickup is cheaper and less complicated than delivery, making it a win-win situation for your small business and customers. 

      It’ll take some logistical planning to get right, so don’t wait until Thanksgiving morning to start planning it out. Implement curbside pickup services as soon as possible so you can test it and refine your strategy before the holiday sales boom.

      Embrace Multichannel Marketing

      The digital world is a big one. There are endless marketing opportunities—too many for your business to do all of them. That’s why it’s important you pick and choose your top priorities for multichannel marketing. Here are a few options to consider for the holiday season:

      • Social Media Marketing: Social media alone has infinite marketing potential. You could livestream, embrace paid social, collaborate with local influencers, and get your community involved in holiday specials and digital events.
      • Email Marketing: Engage your audience with welcome messages, automated emails, cart-abandonment reminders, and timely discounts.
      • SMS (Text) Marketing: Use text messages to send real-time promotions, updates, notifications, alerts, reminders, confirmations, and more.
      • Content Marketing: Content marketing is more of a long-term strategy, but there are holiday tactics like guest posting, influencer outreach, content partnerships, and more you can execute now.
      • Display Ads: Create holiday-specific display ads that’ll deliver the warm fuzzies (and drive sales) during the cold season.
      • Search Engine Marketing (SEM): People will be Googling every imaginable shopping search term out there—make sure your business is competing for eyeballs with holiday-specific promotions.
      • Word-of-Mouth Marketing: Referral programs, online reviews, and affiliate partnerships can drive sales with little cost.

      While it’d be great if you could capitalize on all these digital marketing opportunities, the reality is you don’t have enough bandwidth. Pick 2 or 3 to prioritize, and then focus your time on knocking these marketing strategies out of the park.

      Remember quality over quantity.

      Keep your channels aligned and on-brand. It’s not uncommon for customers to see a deal via social media, email, and your website before making a purchase. There should be a unified marketing strategy across each of your channels that communicates a cohesive campaign.

      Provide Virtual Experiences

      Entrepreneur using computer

      Holiday shopping means different things to different people. Some relish the idea of strolling through the cold wrapped in a winter coat and nursing a mug of hot cocoa. Others love the thrill of fast-paced deal hunting, quick walking (but really actually running) from store to store, down aisle after aisle.

      It’s going to be a different holiday shopping experience this year, and that’s why you need to go above and beyond to deliver unforgettable virtual experiences.

      “All businesses right now should be thinking about connecting with your customers digitally, getting creative in how to acquire new customers, wow the customers you have to improve retention, and watch expenses to preserve cash,” says Jeff Jones, president and CEO of H&R Block.

      Think of ways you can surprise and delight your customers. You might not be able to get Taylor Swift to Zoom-bomb your webinar (wouldn’t that be cool?), but you can execute personalized experiences:

      • Virtual Tours: Show your customers how the sausage gets made. Well, if your product or service lends to a tasteful virtual experience, that is. Take public parties, a group, or even customers one-by-one on a virtual tour of your office. Let them meet the people and see the processes. This is a fun way to humanize your business and introduce new customers to your brand.
      • Face-to-Face Customer Support: Give your customer support calls a human flavor by jumping off the phone and onto the video. If a customer has questions about a product, show rather than tell. Let each customer know they’re important this holiday season.
      • Live Events: Live concerts and local performances are in short supply this year—heck, it’s hard enough for parents to get in to watch their kid’s football game. Give local musicians and artists a digital stage to treat your customers to a special virtual event. An Event Marketer study found that 91% of people who attend a branded event leave with a better understanding of the brand and a deeper connection with it.
      • E-Thank You Notes: Send your customers personalized hand-typed thank you notes for their business—even if they didn’t buy anything. Express your gratitude for your community’s support and say, “Thank you!” It’s the right thing to do, and it’s good for business, too—win-win.

      Capitalize on Each Holiday

      In years past, each holiday catered specifically to specific audiences and industries:

      • Black Friday served the late-night, all-day shoppers who braved the turkey-fueled crowds to snag the year’s best deals.
      • Small Business Saturday encouraged citizens to support their communities by buying local and small.
      • Cyber Monday urged consumers to take a break, relax, recoup from the holiday madness, and shop online all day long.

      However, 2020’s holidays are going to be a bit different. Before November even hit, businesses started promoting their Black Friday deals online. This year, you don’t have to pick and choose which holiday you’re going to give all your time and attention—you can capitalize on all of them.

      Diversify your discounts and your offerings for each special day. If you’re a clothing retailer, you might focus your Black Friday deals specifically on winter coats and jackets. Then, on Small Business Saturday, you could promote your boot collection. Cyber Monday, you could do discounts on beanies and hats. And to cap it all off, harness the power of philanthropy on Giving Tuesday by donating a portion of sales to a movement you’re passionate about.

      By mixing up your deals and keeping things fresh, you encourage customers to return to your digital store day after day. If you have the capacity and creativity, experiment with new deals and promotions on other significant holidays: Green Monday, Christmas, Hanukkah, New Year’s Eve, New Year’s Day, and more.

      Fight the Fights You Can Win

      Entrepreneur looking through inventory

      The online marketplace is a competitive one. Your local ecosystem might include a few direct and indirect competitors, but the e-commerce landscape will pit you against thousands of businesses—big and small. To succeed during the holiday madness, you’ll need to fight the fights you can win.

      You’re not going to win pricing wars or delivery-speed battles with big-box retailers like Target and Wal-Mart, so don’t try. Instead, pick the important fights you can win:

      Embrace Local

      Consumers are aware of the challenges facing small businesses this year, and they’re willing to show their support with their wallets. With 60% of Americans planning to do most of their shopping with local businesses, now is not the time to play big. Embrace your local, small business vibes, and run with it.

      For example, Ray Pugsley, owner of Potomac River Running, is leaning into the small business role with his holiday messaging.

      “We want to highlight that we very much appreciate when you shop with us,” says Pugsley. “We’re a local family, and we’re in your schools and in your community. We are all in this together, so please help small businesses if you want us to be around and in business in the future.”

      Let your community know you need them. Asking your town to support you isn’t a sign of weakness—it’s a humble strength.

      Create Connections

      Regardless of how low their prices are, you probably don’t have a personal connection with your closest Wal-Mart’s floral department. However, your relationship with the owner of the local flower shop is likely genuine. He or she might know you by name, remember your arrangement preferences, and even recall your special someone.

      Those connections make a difference. Create those one-of-a-kind relationships with your customers. Do this with virtual experiences, multichannel marketing, email conversations, and outstanding customer support. 

      Your huge competitors can’t compete when it comes to creating personal relationships.

      Provide Over-the-Top Customer Support

      The holidays are going to be wild for everyone—not just your small business. Offer relief from the chaos by taking your customer support to the next level.

      Need some inspiration? Here are a couple of ways brands have responded to COVID-19 needs

      • Zappos launched an ask-us-anything customer service line. Call Zappos to locate your order, find a delicious pumpkin spice latte near you, or complain about your mother-in-law.
      • Public libraries took the initiative to call library users to check on them. The staff ensured people in the community had food, medicine, and (of course) the books they needed.

      Let these examples inspire your online holiday customer support. How can you provide your community with elevated customer service that big-box retailers can’t?

      If you’ve traditionally relied on phone support in the past, consider expanding your service channels to include social media, chat, video, and email. And if your schedule is jam-packed, consider hiring and training specific customer support help.

      7 in 10 US consumers spend more money to do business with a company that delivers excellent service, so it’s worth your time and energy to invest in top-notch support.

      Turn Your 2020 Around This Holiday Season

      This is the season to overcome the challenges COVID-19, national wildfires, political turmoil, and civil unrest have thrown at your business. It’ll be an exhausting Q4, but it’ll be worth it.

      While the 2020 holiday season will look very different this year, you’re not the only one adapting to change. Consumers, suppliers, lenders, and businesses alike are all dealing with change. Be mindful and sensitive to their needs, too.

      Lastly, remember to prioritize your mental health. This holiday season—with all its unknowns—will be a stressful one. Don’t wait until January 1, 2021, to give yourself the TLC you deserve. Take breaks, delegate, and pace yourself—Q4 is a marathon, not a sprint.

      Executing an online holiday strategy might be something new for your business, but you’ve done much harder things this year—step out of your comfort zone and nail your holiday season sales.

      About the author
      Jesse Sumrak

      Jesse Sumrak is a Social Media Manager for SendGrid, a leading digital communication platform. He's created and managed content for startups, growth-stage companies, and publicly-traded businesses. Jesse has spent almost a decade writing about small business and entrepreneurship topics, having built and sold his own post-apocalyptic fitness bootstrapped startup. When he's not dabbling in digital marketing, you'll find him ultrarunning in the Rocky Mountains of Colorado. Jesse studied Public Relations at Brigham Young University.

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