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Crafting a Holiday Email Strategy That Keeps On Giving

How small businesses are using Black Friday, Cyber Week, and other year‑end sales events to drive year‑round success

Strong holiday sales are essential for many small businesses, building on the momentum of the previous year while laying the groundwork for success in the new one. According to the National Retail Federation, as reported by the New York Times, retailers can earn as much as 20% of their annual revenue in November and December alone, and that number climbs to nearly 30% for hobby and game stores.

If you want to make the most of the other 10 months of the year, Black Friday and Cyber Monday shouldn’t be the first or only time your customers hear from you during the holiday season. Our small business customers sent nearly 9 billion emails alone from Thanksgiving through Giving Tuesday 2021. We’ve seen email sends increase in the month of November 2021 compared to November 2020.

This tracks with a decade-long trend in early consumer holiday shopping. According to the National Retail Federation, 61% of consumers started their holiday shopping by early November in 2021, up from 59% in 2020, 56% in 2019, and 55% in 2018. Shoppers are spending more, too. The NRF forecasts that retail sales in November and December will top out between $843.4 and $859 billion, representing a growth of 8.5-10.5% over 2020.

Larger spends and longer lead times can spell good news for retailers, especially in a year with supply chain disruptions and unpredictable shipping times. And many small businesses have adjusted their email marketing strategies in response. With thoughtful storytelling, increasingly advanced automation tools, and a deep sense of purpose, brands can cut through the noise and use the holiday rush to pull new customers in and generate buildable year-round success. Here’s how.

Introduce yourself.

When you’re speaking to a customer for the first time, it’s important to share more about your business than what you sell. Just ask Be Rooted founder Jasmin Foster, whose inclusive stationery brand is known for its bright, inspiring journals. Almost immediately after the company launched in June 2020, Target came calling with wholesale offers—and the brand has grown ever since. This year, the company’s growth has allowed Jasmin more time to focus on storytelling.

“Last year was my first holiday season, and I was really only using my email strategy to push out promos," she says. "This year, we're leveraging email marketing as not just a promotional tool, but as a way to educate the customer—tell them the backstory behind why we created a collection, engage them with a gift guide, and be more inspiring.”

Foster isn’t alone in thinking bigger than a single promotion or sale. "I want my customers to understand my perspective," says Closed Mondays founder Bekka Palmer, who started using Mailchimp in October as an integration with her Shopify store. "I think customers value your products more if they can relate to you."

Many people find Closed Mondays through West Elm, which sells Palmer’s colorful baskets in its LOCAL online marketplace, so Palmer uses email as a deeper introduction to the brand's ethos, "Whole people build strong businesses.” By connecting her Shopify store to her Mailchimp account, Palmer can sync, view, and act on the customer information she gains from each order, without constantly switching between the two platforms. She uses Mailchimp's customized HTML templates for an on-brand look, and says she hopes to take advantage of more scheduling and automation tools in the future. Rather than pushing a single sale, her holiday newsletters have offered gift guides, supply-chain explainers, and little glimpses at the reality of small business ownership.

"As long as I'm sending newsletters, people end up buying—they just might not buy at that moment,” she says. She tends to get the most engagement on emails with a more human message. "We get a lot of responses. Sometimes, people will even forward it to a friend, which is the most valuable thing someone could do with a newsletter: to say, ‘I thought of you when I read this.’"

Use automations and segmenting to drive connection.

Whether you’re introducing yourself in a welcome sequence or reminding customers to buy the products in their cart, automation tools can impact your bottom line and save you valuable time. But they can also be a crucial way to build personable, long-lasting relationships with your customers. With automated emails, Mailchimp customers see, on average, a 95% increase in open rates and 167% increase in click rates compared to bulk email.

“Our welcome email gets the most opens and clicks out of any email automation that we have set up," says Kristen Strom of Broken Top Brands, an Oregon-based company that sells eco-conscious candles, home goods, and bath products. Strom, who manages content marketing for the company, uses a three-part Customer Journey to welcome new customers into the fold. The first message, a brief overview of Broken Top’s kitchen-table roots, boasts a 55% open rate. From there, the brand sends two more introductory emails with 5 to 7 days in between sends. The second touchpoint, which shares details on Broken Top’s environmental mission, holds a 39% open rate. And the third, which points to company social media profiles and shares blog posts about DIY recycling projects, rings in at 34%.

"It's a pretty cool onboarding process that lets customers know what to expect from us going forward,” Strom explains. “Nurturing those relationships as we sign on those customers, then being able to target them with campaigns, makes for a successful turnaround.”

For Black Friday, Broken Top built on the success of the welcome sequence to bring customers even closer. “A few days before our sale launch, we sent a message to incentivize subscribers who were not on our text subscription to sign up and learn about the sale first,” says Strom. The pre-sale email garnered a 32% open rate and a remarkable volume of orders—all before Broken Top's holiday promotions officially began.

Even so, Black Friday and Cyber Monday remain heavyweights when it comes to holiday shopping and promotions. In fact, from Thanksgiving Day through Giving Tuesday, Mailchimp customers sent over 100 million automated emails.

At Broken Top, the discounts changed almost every day, providing a timely hook for each campaign. On Giving Tuesday, for example, Broken Top reached out to subscribers about a partnership with One Tree Planted, pledging to plant one tree in Oregon for every product sold. Once the initial holiday rush is over, Strom will use engagement data from this email to segment Broken Top’s audience, devoting special messages to customers who clicked through on links about environmental service. “We’ll follow up with those consumers later with the giving update and the difference that we made,” she says. “Our brand messaging doesn't always include the strongest call to action or the most sales-driven messages. We're just trying to really build the best relationship we can.”

Share your values.

At Closed Mondays, the name says it all: Palmer hopes to inspire customers and other business owners to clock out and take more time for themselves. (Yes, her studio really is closed on Mondays.) “The general philosophy of Closed Mondays is that you can have a whole life outside of work,” she says. She shares messages about reducing consumption, increasing your quality of life, and seeking out new experiences.

Meanwhile, much of Broken Top Brands’ messaging is devoted to environmental causes—something Strom says especially motivates its millennial customers. The company recently announced that it would pledge 1% of its total annual revenue to environmental causes. "Through 1% for the Planet, we work with One Tree Planted and a local company called Think Wild. The whole team will go out on a Friday afternoon and volunteer," says Strom, who shares updates on these in-person events as well as all charitable giving. "Our subscribers want to know."

And for Be Rooted, every customer interaction—in-store or online—is an opportunity to share the spotlight with BIPOC illustrators and creatives. “I want to be a stationery brand that continues to give space for artists to be discovered by other people,” Foster says. “When you think about shopping aisles—stationery or beauty or cosmetics—they’re these huge white spaces because a lot of the time, people who look like me don't have a seat at the table. It’s really, really important for me to work with artists and to build with artists that are reflective of the communities that we serve.”

The more you communicate authentically with your customers, from opening up about your background to offering ways to give back, the more you’ll foster loyalty and trust.

Take your learnings from the holidays—what marketing tactics delivered results, what products flew from the shelves, and what feedback your customers shared—and develop a personalized post-purchase strategy that keeps existing and new customers engaged year-round.

Published: December 17, 2021

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