If you’re a small business owner staring down the final quarter of the year, it’s officially “go time.” As I write this article, there are exactly 72 days until Thanksgiving and 100 days until Christmas.
For two-thirds of small business owners, holiday revenue is essential for survival. The last two months of every year can mean the difference between winning and losing, and there are a lot of moving parts to watch in the next 100 days. It begs the question, “Do you have a GPS plan to navigate this make-or-break season?”
Right before Labor Day, I sat down with Jillian Ryan from Mailchimp and Simon Worsfold from QuickBooks to talk about how business owners can prepare for what they are calling the New E-Commerce Calendar. It’s a modern roadmap that shows exactly when consumers are primed to spend, and how to meet them where they are. Let’s break it down.
The Myth of Black Friday & Cyber Monday
Most people think the holiday season revolves around Black Friday and Cyber Monday. Sure, they matter, but that’s only part of the story. The QuickBooks 2024 Holiday Shopping Report showed that last season was filled with several high-intent spending moments, including “Twix Miss” (that sweet spot between Christmas and New Year’s), Super Saturday, and the rising star: Small Business Saturday.
Here are four figures from the report that stood out:
- 34% of consumers say they plan to “shop small” the Saturday after Black Friday.
- They’ll do an average of 39% of their holiday shopping on that day.
- 93% of consumers say they shop small during the holidays because of better service, unique gifts, and experiences.
- In 2024, those figures translated into a $76 billion opportunity for small businesses.
My advice for business owners: If you’re putting all your marketing muscle into just one weekend, you’re missing the bigger picture.
Personalization Isn’t Optional Anymore
One of the biggest takeaways from our conversation was this: Blanket messaging doesn’t cut it anymore. Consumers shift mindsets throughout the season! They might be early-bird shoppers in October, discount devotees in late November, or self-gifters in the Twix Miss phase. The key to unlocking these buying behaviors? Data integration and automation.
Jillian called this “connecting the dots” in your marketing. When your tools, such as QuickBooks, Mailchimp, and Shopify, communicate with each other, you can craft targeted messages based on actual purchase behavior.
Here’s an example: Someone buys a toaster oven from your site through Shopify. That data flows into Mailchimp, triggering an automated email with care tips, accessory offers, or a product review request. It’s simple, smart, and scalable.
According to Mailchimp, users who effectively integrate their systems can see up to 25x ROI on their campaigns (that’s not a typo).
Organize Your Data or Get Left Behind
Here’s a stat that stopped me in my tracks: 80% of business data is unorganized or underutilized. Think about that. You could be sitting on a goldmine of customer insights and not even know it.
If you’re trying to create a holiday campaign without first organizing your customer data, it’s like trying to drive across the country without a GPS. You might make it…eventually. But you’ll burn a lot of time, money, and energy in the process. You also might not make it at all.
This is where AI and automation step in. The most successful marketers—Mailchimp calls them “revenue leaders”—are those who use integrations, CRM, and customer data platforms to drive smarter decisions. In fact, 49% of revenue leaders use integrations, compared to just 39% of their lower-growth peers.
A Holiday Plan You Can Build From
To make the most of this season, you need a strategy. Here’s your 2025 Holiday GPS plan in four steps:
- Segment your audience: Use your data to identify early shoppers, discount seekers, and last-minute gifters. Create campaigns that speak to each one.
- Automate smartly: Set up workflows based on real behavior, such as post-purchase emails, abandoned cart nudges, and re-engagement series. These workflows will help separate the winners from the losers this holiday season.
- Integrate your systems: Connect your sales, marketing, and accounting platforms to streamline operations. Mailchimp integrates with over 250 tools! There’s no excuse for data silos anymore.
- Plan for every phase: Don’t just focus on Black Friday. Build campaigns for Twix Miss, Small Business Saturday, Super Saturday, and beyond. There are now fewer than 100 days until Christmas. Every day counts.
Bricks or Sticks—You Decide
For those reading this who follow me on social media, you’re aware of the company I co-founded with Jocelyn Ring during the pandemic, called Bricks or Sticks. We hosted workshops and podcasts to help thousands of business owners build solid foundations for their companies, ones that could weather almost any storm.
This holiday season, there will be two kinds of GPS plans put together by business owners: Those using sticks, throwing together last-minute sales ideas hoping for magic, and those using bricks, laying strong foundations with data, systems, and strategy.
Be the brick builder.
Start now. By the time Black Friday hits, your systems should already be running like a well-oiled machine, not stuck in setup mode.
The holiday season is a massive opportunity. With a clear GPS plan, the right tools, and a personalized approach, you can do more than just survive; you can thrive.
Brian Moran is an accomplished, award-winning Founder and CEO with three decades of proven success in the SMB space. He is a master storyteller, sales leader, strategic marketer, top SMB expert, mentor, and connector.
Photo courtesy Andrej Lišakov for Unsplash+