Black Friday and Cyber Monday may dominate the holiday marketing calendar, but some of the best opportunities for small businesses could come on the days when fewer companies are competing for shoppers’ attention.
New research from Intuit Mailchimp found that weekend order rates during the 2025 peak holiday season were twice weekday rates, even though businesses sent roughly 60% fewer marketing messages on weekends. The research also found that segmented and personalized emails generated an 11% higher average order value during Black Friday and Cyber Monday.
That doesn’t mean small businesses should simply start sending more weekend emails. Jillian Ryan, who leads content and research at Intuit Mailchimp and has covered B2B marketing, digital transformation and email marketing for over a decade, says the larger lesson is to look beyond the traditional holiday marketing calendar, test when your own customers are most responsive, and make every message more relevant.
I asked Ryan what Mailchimp’s data can teach small businesses as they plan their 2026 holiday marketing campaigns — and where they may be overlooking opportunities.
Look Beyond Black Friday and Cyber Monday
Rieva Lesonsky: Your data shows weekend order rates during the 2025 peak season were twice weekday rates, even though businesses sent roughly 60% fewer marketing messages on weekends. What do you think is driving that gap? Are weekend shoppers more ready or eager to buy, is there less competition for their attention, or is something else happening?
Jillian Ryan: There are a few factors that may be working together here. First, shoppers may have more time to browse and buy outside of the workweek. At the same time, brands tend to pull back because it’s outside of the traditional workweek. One possible explanation is that shoppers are more receptive to marketing messages when there is less noise. On weekends, the decrease in messages shoppers receive may allow the messages they do get to stand out. But weekends aren’t inherently or definitively better. Businesses should look beyond the traditional holiday calendar and target their efforts to when their own customers are most engaged.
Lesonsky: How should small businesses interpret that finding without assuming that simply sending more messages on weekends will double their orders? What should they test before changing their holiday marketing schedules?
Ryan: Every business has a different customer base with different behaviors, actions, and preferences. It’s important for a business to understand its audience before doubling down on weekend messages to increase sales. A good first step is to test a weekend send against a weekday send. Look beyond just how many people opened the messages and focus on how many order conversions each drove. You can also test variables such as timing, offers, and different audience segments. Our data showed that the top 10% of email performers by click rate during Black Friday/Cyber Monday sent 56x fewer emails than other senders. It’s not just about the volume of messages sent, but also their relevance and timing.
Lesonsky: You describe the days surrounding Black Friday and Cyber Monday as potential “white space,” when shoppers may still be engaged but marketing competition is lower. Should small businesses rethink how much of their holiday effort they concentrate on the biggest shopping days?
Ryan: Black Friday and Cyber Monday are important shopping moments for small businesses to prioritize, but the days around them also create an opportunity. For example, Mailchimp customers sent 59% fewer emails and 83% fewer text messages on the Sunday between Black Friday and Cyber Monday compared with Black Friday. Customers are still engaged on these shoulder days, so reallocating some effort to these less competitive moments can help small businesses stand out without trying to outspend larger brands.
Make Holiday Marketing More Targeted
Lesonsky: The report found that segmented and personalized emails during Black Friday and Cyber Monday generated an 11% higher average order value. What level of segmentation is realistic for a small business with limited customer data and marketing resources? Where should they start?
Ryan: For a small business, the key is to start small and use the data you already have. For example, new versus repeat customers, recent customers versus those who haven’t purchased recently, or highly engaged customers versus less engaged customers. You can also use simple behaviors to tailor messaging. Someone who abandoned their cart before placing an order should receive a different message from a loyal customer who has made multiple purchases. The goal is to move away from treating every customer exactly the same and make the message more relevant where you can.
Lesonsky: Email and SMS appear to play different roles during peak season. How should a small business decide what belongs in an email versus a text — and how can it use both without overwhelming customers?
Ryan: Both email and SMS can be valuable channels, but they serve different purposes. When deciding which to use, think about the content and the goal. Email is a great channel for depth and detail. It gives you more room to tell a story, explain an offer, and build excitement over time.
SMS, meanwhile, is best for timely messages such as limited-time sales, limited inventory, or early access. Because of those differences, the two channels can work together rather than duplicate one another. And the data reinforces this: during peak season, SMS reached order rates up to 6x those of email and generated 3x more revenue per message, while email drove the majority of overall revenue. The strongest strategy is to use each channel intentionally rather than sending the same message across both.
Lesonsky: Were you able to break these findings down by business size, industry, geography, or type of customer? In particular, did smaller businesses and merchants show the same weekend and “shoulder day” patterns as the overall Mailchimp customer base?
Ryan: For this report, we looked at aggregate global data from active Mailchimp customers across our free and paid plans, rather than breaking the findings out by business size. So, we can’t say that smaller businesses experienced the exact same weekend and shoulder-day patterns. But the broader takeaway is still useful: These findings can give small businesses new moments and strategies to test with their own audiences.
Rather than treating weekends or shoulder days as a universal rule, look at your own engagement and order data, experiment with timing, and see where your customers respond. For a small business, finding a less crowded moment when your audience is receptive can be especially valuable because you’re not necessarily competing on marketing volume or spend.
Turn Holiday Shoppers Into Repeat Customers
Lesonsky: Holiday marketing often focuses on acquiring customers, but what does your data tell you about first-time buyers? What should a small business do during the holiday season to increase the chances that a first-time buyer becomes a repeat customer after the holidays?
Ryan: Our report found that first-time buyers are extremely valuable. During Black Friday and Cyber Monday, new customers had a 21% higher average order value than repeat customers through email and a 39% higher average order value through SMS.
First-time customers also made up 59% of email orders and nearly 70% of SMS orders. So, while first-time buyers are clearly valuable during peak season, they also represent an opportunity to build longer-term customer relationships. We found that 16.6% of new customers acquired during peak season made a repeat purchase in Q1, taking an average of 26 days to make their next purchase.
To support repeat purchases, small businesses should have welcome, post-purchase, and re-engagement campaigns ready before the holiday rush begins. These intentional steps help customers feel more valued and keep them engaged for the long haul.
Lesonsky: If a small business owner looked at their holiday marketing calendar today and could make only three changes based on what you learned from the 2025 peak season, what would you tell them to change?
Ryan: First, test beyond the obvious, popular days during peak season. Make room to test weekends and the shoulder days around Black Friday and Cyber Monday to see whether you can break through during those less crowded moments with your customers.
Second, make sure your messages are targeted. Start with simple segmentation based on data you already have, such as purchase history or customer status, and send tailored messages to different segments rather than the same promotion to everyone.
Third, plan early for the long term beyond peak season. The holidays are an important period for customer acquisition, so build a strategy that carries that momentum into Q1 and supports longer-term customer relationships.
My Takeaway
Small businesses aren’t going to outspend major retailers during the holidays — and they shouldn’t try to out-message them either.
The opportunity in Mailchimp’s research is to be more strategic about when and how you reach customers. Test days when inboxes may be less crowded, segment customers using the information you already have, and give email and text different jobs instead of blasting the same promotion through every channel.
And don’t treat a holiday purchase as the finish line. First-time buyers accounted for a significant share of peak-season orders, but only 16.6% made another purchase in the first quarter. Have your post-purchase and re-engagement marketing ready before those new customers arrive.
The goal isn’t simply to get more holiday orders. It’s to use the holiday rush to create customers who will still be buying from you in 2027.
Photo courtesy Fellipe Ditadi for Unsplash+