The holiday season can be both the most profitable and the most stressful time of year for retailers. Sales surge, customers behave differently, and even your most reliable products may not follow their usual patterns. Without data, it’s easy to misjudge what’s working—or to miss opportunities hiding in plain sight.

Fortunately, Square Analytics gives you real-time insight into what’s happening across your store network. With new dashboard features (updated for 2025), you can dig deeper into sales trends, customer behavior, and staffing patterns to make smarter, faster decisions that actually impact your bottom line.

Here’s how to use Square’s analytics tools to prepare, execute, and optimize your holiday strategy like a pro.

Start With Last Year’s Data to Build This Year’s Strategy

Before diving into this year’s numbers, take a step back and look at what worked last year. Open your Square Dashboard ? Reports ? Sales Summary and select November and December of the previous year. You’ll get a full breakdown of your top-performing products, peak sales hours, and total revenue during the busiest stretch of the season.

Pay close attention to:

• Top-selling products and categories: These show where customer demand naturally spikes.
  
• Days and times of highest transaction volume: Perfect for scheduling staff and planning promotions.
  
• Average ticket size: A higher average might indicate successful upselling or gift bundling.
  

Once you’ve reviewed your Sales Summary, go to Reports ? Sales Trends for a visual breakdown of how your sales fluctuated throughout the season. This report helps you spot recurring spikes (like Small Business Saturday or mid-December rushes) and anticipate inventory needs before you’re scrambling to reorder.

By studying your historical data, you’ll better understand what your customers want—and be able to align your promotions, stock levels, and staffing accordingly.

Identify Best and Worst Performers in Your Current Inventory

Next, shift your focus to what’s happening right now. Open Reports ? Item Sales to see your top-performing products ranked by both quantity sold and gross sales.

This data is incredibly useful because it shows both popularity and profitability. An item that sells quickly but generates low profit margins might not be as valuable as a slower-moving, high-margin item. On the other hand, a high seller that’s frequently out of stock could indicate an opportunity to reorder more aggressively or renegotiate supplier terms.

Also, sort by Lowest Selling Items to uncover hidden inefficiencies. If something’s been sitting on your shelves since spring, it’s time to discount or bundle it. You can use Square’s Sales by Category report to see which groups (like “Holiday Gifts” or “Grab & Go Snacks”) are performing best.

If you run multiple stores, visit Reports ? Sales by Location to compare how each store is doing. You might find that a product that underperforms in one area is a top seller elsewhere. This insight lets you transfer stock intelligently rather than ordering new inventory unnecessarily.

With this data in hand, you can decide which products deserve prime in-store placement—and which need a pricing or promotion rethink.

Use Real-Time Tracking to Stay Agile

Even the best seasonal plans need adjusting in real time. That’s where Square’s Live Sales Tracker comes in. This dashboard widget updates every few minutes with sales data from your connected POS systems, giving you a live snapshot of how your day is going.

If you notice that certain items are selling faster than expected, you can:

• Reorder immediately from your supplier before running out.
  
• Reprint or update shelf labels using SwiftLabel to mark them as “Hot Items.”
  
• Move popular items closer to the front of the store to increase visibility.
  

Conversely, if a promotion isn’t performing as well as expected, check Reports ? Discounts to see how often customers are redeeming offers. If redemption rates are low, you can adjust your signage, tweak your POS settings, or pair the discount with a complementary item to increase appeal.

Real-time data helps you adapt fast, keeping your promotions relevant and your shelves stocked when it matters most.

Optimize Staffing and Labor Costs

One of the most powerful—but underused—features of Square Analytics is Reports ? Labor vs. Sales. This tool lets you see how your staffing levels align with sales volume throughout the day.

By reviewing this report, you can ensure that you have your strongest employees working during the busiest hours, and you can scale back during quieter periods. Pair it with Sales by Hour for even more precision—this report shows exactly when transactions peak, so you can schedule breaks, cleaning, and restocking during off-hours.

For example, if you see a pattern where Friday afternoons consistently bring higher traffic, you can assign your most experienced team members to handle upselling and checkout flow during that time. Not only does this improve customer experience, but it also helps you avoid burnout and overtime costs during the busy weeks ahead.

Align Analytics With Your Merchandising Strategy

Square Analytics doesn’t just help you understand what’s selling—it helps you design your store around that information.

If the data shows that grab-and-go snacks or small impulse items are selling quickly, consider placing those near the checkout. Use SwiftLabel to keep shelf prices accurate and easily updatable when discounts change.

For high-margin items that aren’t moving, adjust your displays. Move them closer to related bestsellers or promote them with eye-catching signage. When data shows an item performing well online or after social media posts, feature it prominently in-store.

Data-backed merchandising turns your layout into a living strategy—one that reflects how customers actually shop, not how you think they do.

Turn Analytics Into Action This Holiday Season

Square’s 2025 dashboard makes it easier than ever to turn numbers into strategy. By digging into your Sales Summary, tracking live performance, and connecting data to labeling and layout tools like InTrac and SwiftLabel, you can stay ahead of the chaos this holiday season.

The most successful retailers aren’t guessing which items will sell—they’re watching, adjusting, and optimizing in real time.

If you want help integrating your Square Analytics with inventory, labeling, and layout tools, MarketSquare Tech can help you connect the dots. Our team specializes in syncing Square data with systems that keep your store organized, accurate, and ready for the rush.