If you’re a business owner staring down the final quarter of the year, it’s officially “go time.” As I write this blog post, there are exactly 71 days until Thanksgiving and 99 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 99 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 Mailchimp’s latest report, Holiday Shopping Unwrapped. It’s a modern roadmap that shows exactly when consumers are primed to spend, and how to meet them where they are.
The Myth of Black Friday & Cyber Monday
Most people think the holiday season revolves around Black Friday and Cyber Monday. Sure, they are key dates, but that’s only part of the story.
The Holiday Shopping Unwrapped report outlines seven distinct shopping phases, each with its own emotional drivers and spending habits. Understanding these phases is the first step to planning your campaigns:
- Early Lead-Up (October)
- 43% of shoppers made at least one purchase tied to a major sales moment in October.
- 69% of U.S. shoppers who considered Amazon’s Prime Big Deal Days were buying gifts for others.
- These are the Gift-Giving Lifers. They are early birds who love checking off lists.
- Pre-Peak Sales (November, pre-Black Friday)
- Holiday cues (music, films, ads) start to warm up consumers.
- For holiday shoppers buying gifts for others, 31% fewer say price is a deciding factor compared to other times of year.
- This phase appeals to Joyful Shoppers who prioritize meaningful gifts over deep discounts.
- Peak Sales (Black Friday, Cyber Monday, etc.)
- 75% of global shoppers made a purchase during at least one peak event.
- Driven by Discount Devotees. They are deal hunters who love the thrill of beating the system.
- Festive Phase (Early December)
- 26% of shoppers make purchases during this time.
- Regional traditions matter: 48% of Benelux and German shoppers purchased on St. Nicholas Day.
- Popular with Curators. This group is filled with thoughtful shoppers seeking unique gifts with stories.
- Last-Minute Sprint (mid–late December)
- Shoppers scrambling to wrap up lists before Christmas (I fall into this category, but I am working to become a Curator or even a Discount Devotee).
- 78% of consumers who buy on Super Saturday (the last Saturday before Christmas) are buying gifts for others.
- Last-Minute Listers are anxious about shipping deadlines and will go with any brand that can deliver on time.
- Betwixtmas (Dec. 26–31)
- A self-indulgent shopping window between Christmas and New Year.
- 68% of shoppers in Australia, Canada, and the UK who considered Boxing Day deals were buying for themselves.
- This is prime time for Self-Gifters.
- New Year (January)
- The mood shifts from giving to self-improvement.
- 63% of European shoppers participating in January sales were buying for themselves.
- Self-Improvers dominate this phase, using sales to support resolutions.
What Did We Learn?
If you’re putting all your marketing muscle into just the Black Friday weekend, you’re missing the bigger picture. There are opportunities every step of the way!
Personalization Isn’t Optional Anymore
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 during Betwixtmas. The key to unlocking these buying behaviors? Data integration and automation.
Jillian calls this “connecting the dots.” When your tools, like QuickBooks, Mailchimp, and Shopify, talk to each other, you can craft targeted messages based on real purchase behavior.
Here’s an example: someone buys a toaster oven from your Shopify store. 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 integrate their systems can see up to 25x ROI on their campaigns (that is not a typo).
Organize Your Data or Get Left Behind
Here’s another stat that stopped me in my tracks. According to several Gartner articles and reports, in 2025 ”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 driving across the country without a GPS. You might make it… eventually. But you will 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 can help. The most successful marketers are the ones who use integrations, CRMs, and customer data platforms to drive smarter decisions. According to Mailchimp’s The Revenue Blueprint report, 49% of revenue leaders use integrations versus just 39% of their lower-growth peers.
A Holiday Plan You Can Build From
To make the most of the upcoming season, here is 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. Mailchimp integrates with more than 250 tools! There is no excuse for data silos anymore.
- Plan for every phase: Don’t focus just on Black Friday or Cyber Monday. Build campaigns for Early Lead-Up, Small Business Saturday, Super Saturday, and Betwixtmas. There are 99 days from today (9/17) until Christmas. Make each day count.
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.
Cue the Christmas music.
