Being prepared for the holiday season isn’t just about optimizing your site for the upcoming few months, but setting best practices to ensure year-round success.

Are you ready for the busiest part of the year? If not – don’t worry! We put together this easy to reference holiday checklist for brands beginning to prepare for the upcoming season. Gearing up for the most important months of retail can feel overwhelming, with so many bases to cover, but with a little organization and strategy you’ll be ready in no time. Many of the topics discussed within are things WeSupply can help with, but this guide expands past that to encompass the full scope of holiday prep.

Already got your holiday planning sorted out? This checklist is still worth a look as these seasonal best practices are also the recipe for year-round optimization and success. Following the initiatives found within this list will elevate you above the competition and prepare you for anything the unpredictable world of retail can throw at you!

Chapter 1

Preparation: Revisiting Last Year’s Data

Get an Early Start!
While the major boom for your store might not occur till November, there are a lot of early shoppers out there.
Make sure your site is optimized to handle this, and take this opportunity to communicate upcoming products and promotions to customers who will want to return for more later.
“In 2018, 86% of consumers started holiday shopping between June & September.”
- Credit Karma
Year over year holiday sales are growing big time, and you don't want to get caught understaffed during the 2019 season.
Use your 2018 data as a guide and prepare to staff appropriately for the projected increase.But what about staffing for e commerce - who's going to process all of those orders?
Easy, you can use your WeSupply dashboard to analyze the average processing time and productivity of each shipping location to make sure each one is staffed according to workload.
"530-590k temporary workers are projected to be hired by retailers during the 2019 holiday season."
- National Retail Federation
Processing Time
As shopping behavior changes, each year finds a bigger portion of holiday sales coming through ecommerce.
Make sure you're prepared to delight your online customers this season by taking the time beforehand to analyze your actual processing time per location as well as the performance of your carrier partner.
Doing so will ensure that you can fulfill the those especially crucial delivery promises that can make or break their experience with you.
By getting ahead of last years problems - late deliveries, theft, miships, etc - you're one step closer to being ready!
"23% of all non food retail sales will take place online this holiday season, up 200 basis points from 2018."
- Coresight
Successful Products & Promotions
When planning holiday promotions and inventory it's important to look at the previous year.
Use this as a starting point to see what worked or didn't work for you, and compare the data with the current market.
Customers are willing to spend money with you, but you need to be competitive to make the sales!
“More than 3/4 of shoppers say they are likely to spend the same or more than last year for the 2019 holiday season.”
- Deloitte Insights
Chapter 2

Behind the Scenes: The Right Tech to Power Your Holiday

Customer Satisfaction
Holiday season is busy, but it's busy across the board.
Everyone has good products and everyone is playing the price war.
How can you differentiate from your competition? By focusing on making customers happy! If you're not sure where you stand in that regard, it's time to start sending the CSAT survey after your transactions.
"Only 48% of polled consumers believe that the brands they buy from care about their satisfaction."
- Neil Patel
Optimized Servers
Your server is good-to-go for regular day to day traffic, but is it prepared for those big holiday spikes? This is especially relevant in you're running any big Thanksgiving, Black Friday, Cyber Monday, or Christmas promotions that are sure to bring an influx of visitors.
Don't lose your opportunity to convert all those customers due to server issues, because once the site goes down they probably won't be coming back.
"2016's holiday season saw significant traffic spikes, including a 207% increase in traffic on Black Friday."
- Magento
Damage Control
Online shoppers have more options today than ever before, so their threshold in dealing with faulty, slow loading, or downed websites is at an all time low.
Still, accidents do happen, so what can you do to keep customers engaged with you through these tough times? HelpScout recommends you begin by being up front and acknowledging the issue.
Be sure to authentically empathize with customers, avoiding generic phrases and opting instead for a little personality.
Be clear about the scope of the issue and keep the messaging customer-centric, speaking to how the issue affects them.
Own up to the issue without blame and offer alternatives where available.
Most importantly, don't forget to follow up often!
"79% of web shoppers who have to wait too long for sites to load say they won't return."
- Magento
Fraud Filters
Finding a balance for your fraud protection is crucial before the holiday season kicks off.
While an aggressive fraud filter will save you big time on chargeback fees, an overzealous approach can result in the rejection of legitimate transactions (1.5%).
If you aren't prepared to staff your customer service team with extra bodies to manually review transactions during the hectic holidays, it might be a good idea to look into a fraud prevention solution.
While it does present an extra cost, this generally pays itself back quickly in mitigated chargebacks!
"Merchants lose an average of $2.40 to fraud per transaction."
Chapter 3

Sales Drivers

"The numbers are promising, but the competition for those dollars is fierce.
For most brands, this is the time to get promotional, but that doesn't mean you can't be creative and vary the types of promos you run!
-% or $ Discount: These two classic promotions may get used a lot, but as the saying goes, "why fix what isn't broken?"
-Kick Back: Entice customers to spend money now to get a special discount later. This could be really helpful to not only drive holiday sales, but in starting Q1 off with a bang when they come back to spend!
-Mystery Box: Got some old products to get through but don't want to individually mark them down? Offer a mystery box to lessen prices without damaging the reputation of any specific item. The value of the bargain and the excitement of the marketing will drive customers to purchase items that would otherwise sit. Plus, they'll get some extra items to gift to others as well!
-Gift with Purchase: Gain an edge over your competition by offering a free gift with products purchased during the holiday season. Make it a thoughtful item that compliments the original purchase for best results."
"56% of consumers will shop online in 2019, seeing a sales increase of between $162.6 billion & $166.9 billion this season."
- National Retail Federation
Gift Wrapping
So, why not offer to do it for them? Giving customers the option to select a gift wrapping add on has been a tried and true holiday tactic for years now.
Get creative in how you present it; you can use an automatically updating header that changes with customer's cart value, a popup after the item is added to cart, or by an add on in the cart.
It's up to you but whichever method you choose you are making big strides toward improving customer experience/satisfaction and rising above your competition.
"52% of customers dislike wrapping presents because it takes too much time."
- Statista
Chapter 4


Start Marketing Early!
While most customers are still in the research stage during the month of October, it's a good idea to have your site up and running optimally beforehand to take advantage of early bird shoppers.
Even more importantly, this is a key opportunity to make an early impression on potential customers.
Succeeding at doing so now will drive future sales while beating the rising marketing costs of the upcoming months.
"54% of shoppers began researching holiday gifts in (of before) October, with 33% making purchases at that time."
- National Retail Federation
Customer Retention
Your customers are paying attention to the deals that you're offering during the season, but how can you increase the odds that they'll convert when there's so much other noise to compete with? Easy.
Go out out of your way to tell them about a special deal or value they're getting due to their loyalty.
Once they can confirm this through research they'll feel like they're being treated in an elite, personalized way, and will be more likely to purchase.
"Brands that spend more on customer retention have over 200% higher chance of growing their market share."
- Total Retail
Educate Customers
As more and more customers join 'team early' in preparing for their holiday shopping, it's a big opportunity for you to get ahead of the season and educate them on your upcoming products.
Building excitement now with your existing base is critical to maximizing your potential sales.
"40% of people start their holiday shopping before Halloween."
- BigCommerce
Chapter 5

The Product Page: Optimizing the Pre-Purchase

Create Urgency Through Holiday Deadlines
Appeal to last minute shoppers by letting them know they can still get their items in time! Creating a sense of urgency is an amazing tactic to drive conversion, especially when there's a specific date deadline.
Clearly letting customers know that their order will arrive before Christmas if placed within x time frame will prompt them to act fast.
This strategy doesn't just work on it's own though, as it's dependant upon a few other elements.
These include trust, relevancy, and moderation - because this technique loses its effectiveness if you play it out!
“The final week before Christmas accounted for 12% of visits and 14% of transactions of the entire holiday season, in 2017"
- John Fetto, Hitwise
Rich Product Descriptions
"Product descriptions work alongside images to paint your items in the best light possible for customers - so needless to say this should be optimized year round.
Neil Patel put together a checklist to help write powerful product descriptions that sell.
- Define you buyer personas before writing descriptions.
- Use features and benefits to motivate purchases.
- Reflect your brand's tone of voice.
- Create scannability through bullet points.
- Use influential words to boost persuasiveness.
- Optimize for SEO
- Use more images & mixed media."
"86% of consumers rate product content as 'extremely' or 'very' important in a buying decision."
Quality Images
Yup, that's about half a glance.
Strong imagery acts like a window to your products - it's often the first step toward the momentum that leads to a purchase.
Good product images should enrich your content and speak to your target audience.
"50 Milliseconds (the amount of time it takes a customer to make their first impression of a product.)
- Shopify
Delivery Date Estimates
Estimated delivery dates sit at the center of a well put together pre-purchase experience.
They mitigate potential shipping anxiety by setting correct expectations from the start, and this is especially important during the holiday season where arrival dates mean everything.
Would you still buy that gift if it might arrive somewhere from Dec 23-Dec28th? Yeah, we didn't think so.
"40% of the major US ecommerce checkouts we benchmarked show shipping speeds instead of delivery dates."
- Baymard Institute
Modern day online shoppers want a tailored experience.
The best time for this re-engagement is during the post-purchase stage, as this is when customers are most eager to hear from you.
Use your transactional emails and SMS messages to link to a fully branded tracking page.
Here you can present customers with the appropriate content to better use the their purchases and recommend relevant upsells.
“In 2018, 87% of marketers accredited personalization marketing to their sales lift.”
- Evergage
When in doubt, ecommerce customers look to their peers to help them make a decision.
Make sure your product page is optimized for conversion by adding user-generated reviews.
These play a major role in influencing purchases because they build trust and mitigate anxiety.
"90% of consumers read reviews before purchasing!"
- Constant Contact
Q&A Section
Q&A's are particularly helpful for new customers who may not be very knowledgeable about your brand or products.
Because of their inexperience, they are extra weary of potential post purchase dissonance.
A user generated Q&A section highlights actual use-cases from real life customers in order to build trust and validate the claims made in your product description.
"25% of tested customers scanned the Q&A section for product information, despite not having a specific question."
- Baymard Institute
Size Chart & Guide
Sizing is the foremost reason customers cite when asked why they chose to shop at a physical store rather than online.
This is no good for ecommerce-only retailers who can't provide the brick & mortar experience.
A clear and easily accessible size chart on the product page can help boost customer confidence, increase conversion, and dramatically reduce returns by taking the guesswork out of the purchasing process.
"80% of online apparel returns are due to fit issues."
- Morgan Linton, Fashion Metric
User Generated Images
User generated content speaks volumes to your millennial customer base, and that translates into sales.
Images from sources such as Instagram can improve conversion rates up to 2.4x, especially for apparel, jewelry, footwear, beauty, and consumer electronics.
Let your customers inspire your soon-to-be new customers!
"51% of US consumers now trust user-generated content about a product more than other information on a company website."
- Bazaarvoice
Notify Customers When Items are Back in Stock
Often times an out-of-stock situation is the end of the road as far as the potential to make a sale.
You can combat this by recapturing sales through the utilization of back in stock email alerts.
Offering this option also succeeds in ending the interaction with an event so customers don't feel as though they've wasted their time.
Even if they don't end up purchasing this item later it's a good chance for you to re-engage with them and spark their interest in your products.
"Shoppers encounter out-of-stocks in as many as 1 in 3 shopping trips."
- Celect
No more Out of Stock
“Out of stock” is a real UX dead end that doesn't let customers go any further on a site if they are truly set on purchasing a particular item.
Many retailers are wising up and opting instead to make the product available for purchase while adjusting the estimated delivery date to reflect the gap in availability.
This lets users complete the purchase with you, perhaps adding other items to their cart as well.
"30% of customers are likely to abandon and look elsewhere when told a product or product variation is out of stock."
- Baymard Institute
Chapter 6

Returns Returns Returns!

Market as Free or Easy
Free returns are the ultimate conversion booster because they mitigate the risk factor for post purchase dissonance.
The customer knows they won't have to live with the regret of a bad purchase if they can simply ship the item back and wipe the slate clean.
This is especially important for brands selling more expensive, big ticket items.
Also, it's worth noting that perception is indeed reality.
So even if you don't feel comfortable offering free returns during this holiday season you can still market them as "easy" to draw attention to your policy and put customers at ease.
“27% of shoppers say they would purchase an item costing over $1,000 if offered free returns, but only 10% would do so if it not.”
- Bigcommerce
Avoid Policies That Block Sales
We know, we know - no retailer wants returns.
However, making the process harder for customers is actually doing your brand a disservice.
Many modern-day online shoppers won't even risk making a purchase if the returns policy looks too strict or complicated.
Instead of viewing returns as a bad thing, it's better to accept them as a part of the e commerce experience and use them to your advantage.
An effortless policy can increase conversion by mitigating the anxiety around post purchase dissonance.
In the event that the return needs to be made, a good policy can also create loyal customers out of an initially bad situation.
"11% of users have abandoned at least one order in the past quarter solely due to an unsatisfactory returns policy on the site."
- Baymard Institute
Add to Terms & Conditions
You need to put the returns policy in an easy to find place for your customers.
Tucking it away in a seldom visited section of your site will oftentimes stop your chance at converting a customer before it even got off the ground.
Even if they assume you may have it listed in another page, they likely will not put forth the effort to find it on their own.
Be proactive and properly display, or link to, your returns policy in easy to find places.
"60% of consumers review a returns policy before buying."
- Accenture
Extend Return Dates Post-Holiday
Buying gifts for a lot of people is stressful enough without having to worry about if each individual recipient will be able to return or exchange the items they don't love.
Ease these pre-purchase anxieties with a relaxed or extended return policy through the holiday season.
Not only will this increase your holiday conversion rate, but presents an opportunity to re-engage with gift recipients that otherwise may not have shopped with you.
"1/3 of holiday shoppers say a store's return policy is an important factor when deciding which retailer to shop."
- National Retail Federation
Store Returns
By giving BORIS (Buy Online Return In Store) equal representation as mail back returns, you gain the advantage over your ecom-only competition.
Many customers prefer this method of return because it; allows them to ask questions about the policy, offers a quicker refund, saves on return shipping, and is simply more convenient.
Retailers should promote this method because while they have customers in their brick & mortar location they can "wow" them with an incredible experience and showcase the latest products and promotions to drive future sales.
"20% of consumers still say they prefer making their returns in-store."
- Baymard Institute
Self-Service For Convenience
When it comes to returns it's not always about the end result, but about the effort it takes to get there.
Most customers want to solve problems on their own without wasting valuable time on the phone with customer service representatives - so give them what they want.
By offering a self-service driven returns flow you empower customers with the ability to efficiently handle their issues and reduce unnecessary friction points.
This also frees up your agents for bigger issues that are bound to arise during the busy holiday season.
"81% of customers try to help themselves before contacting you."
- Bigcommerce
Self-Service For Cost Savings
Returns are a necessary part of ecommerce, but they don't have to eat into your bottom line.
Make sure your returns flow is optimized to preserve your margin before the influx of holiday orders hit.
By working smarter you can save cost, delight customers, and use re-engagement to drive repeat sales.
"Return expenses for an organization can be anywhere from 20%-65% of the cost of goods, with poor execution and policies exacerbating the problem."
- Jack Rheude, RedStag
Label in Box: Yes or No?
Putting pre-paid labels in the box is a hot subject among e commerce analysts.
They make things convenient for customers, but they drive up costs, increase the likelihood of returns, and offer retailers no actionable data about why the item is being sent back.
Employing a self-service returns flow that can be initiated by customers through a "my account page" solves all of these issues but there's a catch - it has to feel just as easy for the customer.
If they can't figure out how to make their return they will likely be on the phone with your service team exerting way too much effort.
Whichever side of the fence you're on, just make sure the experience is effortless for the customer.
"34% of customers want to see a prepaid return shipping label in the box."
Gift Returns
In a perfect world, every gift we pick out would be a hit.
Sadly the data shows that this usually isn't the case.
Making a gift return for an online purchase can often be a nightmare, especially when the recipient doesn't have access to the gift givers account.
Simplify the process for gifted customers by allowing them to make a return without needing to involve the original purchaser.
Let them initiate their return after asking for their order number, email, and zip - information they'll readily have available.
"The 2017 holiday season saw 28% of the gifts people purchased returned, at a value of $90 billion."
- Small Business Trends
Reduce Friction
In order to navigate the competitive landscape of e commerce during holiday season you have to give customers what they want.
In most shoppers, this want is to feel at ease.
How can you give this to them? Easy - with a flexible, effortless returns policy.
Knowing they can easily make a return helps customers trust your brand by mitigating pre purchase anxiety and potential post purchase dissonance.
"82% of consumers consider the returns policy to be important when making an online purchase."
- Accenture
Chapter 7

Proactive Notifications: Mitigating Anxiety & Delays

Opting into SMS Notifications
Are you communicating with your customers through their preferred channels? For most consumers this is SMS notifications, as illustrated by their immaculate open rate.
For best results make sure to give customers the choice of opting into these transactional text messages immediately after placing an order as well as keeping the option available on their order detail page.
"90% of SMS notifications are read within 3 minutes of delivery."
- nopCommerce
Order Confirmation Email
Order confirmation emails are so effective because this is when your customers want to hear from you the most.
Make sure you're sending one out as soon as the customer places an order to build their trust and mitigate any potential buyer's remorse.
Order confirmation is the building block of a strong post purchase transactional email strategy that offers unbeatable ROI and re-engagement possibilities - just in time for all of those new holiday season customers!
"Order confirmation emails generate about $0.75 per email, while bulk mailings typically generate around $0.13 per email—that’s nearly a 6-fold increase in ROI!"
- Experian
Shipping Confirmation Email
"From the moment the order is placed this is what the customer is patiently waiting for.
Make the most out of your shipping confirmation email by including access to two very important pages. Order Detail Page: Include all relevant item and shipping information, including if the shipment was split into multiple packages. Tracking Page: Not only is this a big opportunity for you to keep customers in the loop, but also re-engage them with branded imagery and shoppable banners."
"64% of consumers consider transactional emails, including shipping confirmation, the most valuable messages they receive."
- Litmus
Delivery Delays
As the holiday season sees an increase in 2 Day shipments there comes boost in shipping delays.
These can come in all shapes and sizes; bad weather, logistical issues, wrong address, missing delivery instructions, and the list goes on and on.
Aside from an impending late arrival there's another commonality between all of these situations - what you can do to mitigate them! Delivery updates through email and SMS notifications keep customers one step ahead of the process at all times, so they can redirect packages, change instructions, and much more.
Even though these issues are largely with the carrier, customers won't forget that you played a part in helping them sort it out and didn't leave them hanging out to dry.
"15-23% of shipments are delayed during the holiday season."
- Sri Sridhar, CEO
Stopping Theft
As you prepare to increase your volume of shipped packages this holiday season, make sure you're ready for the uptick in stolen packages as well.
Instead of waiting for issues to arise, you can help mitigate them before they happen through proactive notifications.
By sending customers an email and SMS notification when their package is delivered it reduces the time it sits on the front step.
Customers can quickly get their package inside and away from potential thieves!
"8% of Americans (over 25.9 million) have had a package stolen during the holiday shopping season."