Holiday Delivery Planning: How to Prepare Your Business for the Seasonal Rush

Online shopping is the new norm in 2025. In the U.S. alone, 288.45 million people shop online (that’s over 84% of the population). Globally, e-commerce sales are expected to hit $6.42 trillion this year. A large percentage of those sales will likely come from the holiday season.

And if this year is anything like the last, shoppers will show up online in droves on the two biggest shopping holidays: Black Friday and Cyber Monday. Last year, shoppers spent a record $10.8 billion shopping online on Black Friday. This year? An estimated 38% of consumers will shop online, and 22% plan to spend even more this year.

For local delivery businesses in particular, online shopping opens a whole new world of opportunity for growth, especially during the holiday season. 

But are your inventory management and delivery systems ready to handle an influx of online orders and deliveries at this time of year?

We’ve put together a 4-part guide to help:

• Create a holiday buying experience that will attract customers
• The Holiday Shipping Experience
• The Holiday Delivery Experience
• Your Holiday Season e-commerce Preparedness Checklist

How to create an attractive holiday buying experience

Online shopping for the holidays isn’t like other times of the year.

Customers feel they have more choice, but less time. The urgency to buy is up, but so is distraction and friction. As a small business, you have to not only make the case that your product is good, but that buying from you is just as good as buying from Amazon or Target — or even better! 

Here are some you can ensure your holiday shopping experience stacks up:

1. Know your dates and promotions

Don’t make the mistake of beginning to think about the holidays in mid-November. Most customers start their holiday shopping during the Black Friday/Cyber Monday (BFCM) weekend (November 28th to December 1st). 

In the month before that, you should also be thinking about how you’re building your email list for the holidays and whether to run a pre-BFCM sale to avoid the November sales dip as customers anticipate the big weekend.

A typical promotional schedule might look like this:

• November 1-15th: Contest or campaign to build your email list
• November 28-December 1st: Your biggest discounts of the year (20-50% off is standard)
• December 10-21st (depending on your delivery or shipping options): “Last Chance for Christmas” campaign for last-minute orders
• December 26th-31st (especially in UK/Canada/Australia): Boxing Day promotions (10-30% off)

2. Set realistic cutoff dates and timelines

Make sure your customers know exactly how long it takes for their order to come, and when they need to order by to get it for Christmas Eve. With Christmas, it’s best to err on the safe side. If you or your shipping partner typically takes 3-5 days to deliver, set the cutoff 6 days ahead.

Even before Christmas, it’s important to put your holiday season shipping expectations front and center on product and discovery pages.

3. Communicate clear return policies

Nearly 39% of shoppers return an item they purchased online at least once a month. Customers now expect to be able to return products, and when buying gifts, this is even more important. Whether you choose to have a generous return policy as a marketing strategy, or a tight one to stay profitable, make sure your customers know.

4. Offer gift wrapping or gift packaging  

This is the obvious one. If you’re thinking about adding a gift card, gift wrapping, or gift package feature, now’s the time to do it. Customers will appreciate the ability to do it, especially if you can make it an all-in-one solution with shipping to a different receiving address available.

5. Be transparent about packaging

The holiday shopper isn’t just thinking about getting the product — they’re thinking about giving it. If you have gift-ready packaging, that can help you distinguish yourself from the customer’s sea of brown boxes. For example, you could ship a gift-wrapped package inside a mailer envelope and include a blank card; or you could invest in custom packaging that’s gift-worth in itself.

If your product is perishable or high-value, this is even more important. You’ll need to make it clear how you preserve the product in transit, how long it can stay cold (or warm) at a doorstep, and how important it is to make sure they’re there to receive it.

How to deliver a great holiday shipping experience

Some small retailers make the mistake of thinking their e-commerce experience starts and finishes online. For the holiday season, in particular, that’s only the beginning. 

This is the most stressful and exciting time of the year for your customers, and the shipping experience is your chance to both alleviate the stress and tap into the excitement to wow your customers.

Whether you’re shipping through a 3rd party, managing it yourself, or a mix of both, here’s what you need to consider:

1. Send a clear post-purchase email

Some people think that the info in a post-purchase email is only useful immediately after purchasing. That’s not actually true. 

Part of the benefit of having a clear, well-branded post-purchase email with clear details about shipping is to be a reference point for your customer. They will appreciate the ability to go back later and check when their package is coming, and it will save your logistics and support teams time.

2. Offer multiple shipping options

The more flexible your shipping, the more sales you unlock. One way to do this is to provide options for third-party shipping, pickup, and local delivery options. 

• Third-party shipping: Shippers like USPS, FedEx, UPS, and DHL help you cover larger areas and meet demand, but they also have costs and risks. Even in 2024, businesses were still seeing supply chain disruptions, with 15% of shipments seeing delays. 
• Local delivery: If you mainly serve customers in your local area, you can save money and offer a better delivery experience by managing your own deliveries. Delivery software like Routific makes it easy to plan efficient delivery routes. 
• Pickup: Giving your customers the option to pick up their orders at a warehouse or in-store means you have zero delivery costs. Customers might also browse and buy more once they’re in your store. 

Local delivery and pickup options also mean you can offer your Christmas delivery guarantee for longer. We’ll cover delivery aspects and meeting holiday demand more in-depth later on.

💡 Need help managing your local deliveries? Our delivery management software can help you make your local deliveries with ease.

3. Make it easy for customers to track their deliveries

Nothing frustrates a customer more than a package lost somewhere during the delivery process. If you’re using third-party shipping, make sure you’re sharing tracking numbers as soon as possible, and if you’re using local delivery, make sure your customers know the status of their orders in real-time. Automated customer notifications are the easiest way to do this.

4. Prepare for extra customer support needs

During the holiday rush, you can expect your volume of customer support requests to go up along with your volume of orders. 

Make sure you have a larger team (or extra time set aside) to address customer questions in a timely manner. Follow shipping best practices like photo + signature proof of delivery, plus the other tips in this guide around transparency and automation, to lighten your load.

5. Use customer notifications

Nothing is worse than missing a delivery, especially during the busy holiday season when stress is high. Keep your customers posted on your deliveries with SMS notifications and live GPS tracking so they know exactly when their orders will arrive. This is particularly important for high-value or perishable goods.

Customer notifications are also a brand touchpoint. Make sure they’re customized to your voice so customers feel the love!

6. Make the unboxing experience special

The unboxing experience isn’t just about a box with your brand colours. It’s about ensuring your product comes exactly as promised. 

This pre-holiday season is a good time to stress test your packaging:

• Can it withstand being dropped or bumping around? 
• Are the products secure in the box? 
• Is your shipping’s temperature control up to standard? 

These factors can make or break your customer’s holiday.

Planning the holiday delivery experience

A little planning and preparation can go a long way in helping you achieve a successful holiday season. With the right strategy, you can make timely deliveries and create a positive customer experience. That translates to repeat customers and growth.

Ideally, you should start thinking about your delivery experience in October or even September to make sure you’re prepared for the rush. 

Here are some key things to consider.

1. Know how many drivers you need

If you’re making local deliveries, you’ll need drivers — and at peak season, they’ll be in demand. Don’t wait to start planning. Use forecasting and historical data to project:

• Order volume
• Peak days 
• Delivery issues and potential delays that may pop up

This data will paint a clear picture of demand, so you can prepare by hiring more staff.  Students and retired people are often available for extra work at this time of year.

Routific makes it easy to plan for driver capacity. Just set your shift times, and the platform will tell you how many drivers you need. It will even warn you about likely overtime, so you can plan accordingly.  

2. Budget for peak season hires

With a clear idea of your staffing needs, you can budget for shopping season hires. How can you fit temporary hires into your budget? 

Consider:

• Adding holiday surcharges. Many businesses add holiday delivery fees or minimum order thresholds. Customers expect these.
• Hiring gradually. You don’t necessarily have to bring everyone in at once. Scale as the holiday shopping peaks to manage costs without being left with staff shortages. But make sure you start hiring early on (think October or November) to handle that early influx.
• Using contract drivers. Short-term contracts can help you manage the shipping season without needing to expand your full-time staff.
• Launching pre-order or early bird promotions. These special promotions can generate cash before peak hiring.

As a last resort, short-term credit lines can finance the gap and help you manage deliveries during this busy time.

3. Manage customer expectations

Want to boost customer satisfaction during the holiday shipping season? Be transparent about what customers can expect.

• Have a written shipping policy and make it easy to find on your website (including the checkout page) and in emails.
• Post clear shipping deadlines on your website, confirmation emails, and checkout pages. Make sure holiday shoppers know your cut-off dates.
• Clarify delivery timeframes. Don’t just say “standard” or “expedited shipping”. Share how long delivery should take (e.g., 2-3 days).
• Let customers track their orders in real-time, so they don’t have to guess where their orders are. 
• Proactively communicate delays to keep customers in the loop.

Managing expectations can help prevent disputes and improve the overall customer experience. 

4. Use delivery management technology to improve efficiency

Efficiency is always important, but especially when it comes to holiday deliveries. Even with sufficient staff, you still need to make sure your route planning and delivery management systems are helping you keep your cost per delivery as low as possible.

Automation will save you time and help ensure your routes are efficient.

With a tool like Routific, you can:

• Use intelligent route optimization, based on AI and machine learning, to create the most efficient and cost-effective routes.
• Use our free mobile app to easily send routes drivers, collect proof of delivery and get real-time updates on delivery times and driver locations.
• Send customer notifications to let shoppers know when their order is on the way and when it’s delivered. Send ETAs to keep customers in the know about their deliveries.

Routific makes it easy to optimize and streamline your route planning during peak season, so you can stay focused on what matters most: customer satisfaction. 

Staying profitable

It’s all about the customer, but you also need to make money. The costs of the holiday season can add up quickly and eat into your margin, especially through delivery. 

If you’re shipping through third parties, make sure you understand what percentage of those shipping costs you need to pass along to your customers. 

If you’re doing your own local delivery, make sure you’ve properly calculated your last-mile costs, and implement delivery management software to automate route planning and control costs in real-time.

Your holiday season e-commerce preparedness checklist

One month before Black Friday/Cyber Monday, you should:

• Set your promotional calendar
• Set your order cutoffs
• Set your return policy
• Lock in your packaging, packing process, and unboxing experience
• Have gift options prepared
• Update your post-purchase email
• Know your shipping plan and partners (in-house, local, and third-party)
• Set up customer order tracking and notifications
• Ramp up customer service capacity
• Calculate your delivery costs

Recap

The 2025 holiday season is shaping up to be another record-breaker. For those that are able to successfully serve their customers online, they’ll capture new levels of growth and establish long-term customer relationships that translate to year-round sales. But those who fall short on their promises will be playing catch-up well into 2026. 

If you’re ready for your shipping strategy to be part of your competitive advantage, try Routific for free to give your local delivery team accurate ETAs, efficient routes, and most importantly, peace of mind for you and your customer.