2020 Holiday E-Commerce Prep: 40 Tips from E-Commerce Experts


To help brands and retailers optimize e-commerce channels and sell more during this unprecedented holiday shopping season, we asked industry analysts, digital agencies, and e-commerce veterans for their best holiday e-commerce tips.

With a whopping 97% of people doing some of their shopping online this year and only 60% doing their holiday shopping in stores—down from 87% last year—getting e-commerce right this holiday is vital for brands and retailers selling products online.

After unwrapping the responses from each e-commerce expert, we noticed a few trends that brands and retailers should keep top of mind this holiday season:

  • With people overwhelmed from an exhausting 2020, make sales and selection simple.
  • Clearly communicate shipping deadlines and have backup plans for fulfillment and distribution.
  • Create segmented and lookalike audiences based on seasonal behavior.
  • When in doubt, choose to over-communicate (i.e. send more SMS and emails).
  • Continue experimenting with everything from ad copy and images to curbside pickup and AI-driven customer service.

In addition to keeping these trends top of mind, select a handful of specific tips below to implement before and during the holiday shopping season. Choose the tips that make the most sense for your business.

To choose the best tips and maximize the effectiveness of your holiday e-commerce strategy, I recommend reading the entirety of this post. While extensive, every contributor was mindful to reveal deep insights in a succinct way, making this a meaningful read.

Tips for Holiday E-Commerce Success

Bruce Eppinger, Analyst @ Highland Park Advisors

A holiday season like no other is upon us. Some of your best customers will not set foot in a retail establishment this season. They will buy having never touched your products; you will need to re-acquire your customers from the digital marketplaces that capture fifty cents of every dollar that transitions from instore to online. After twenty years of omens and opportunities to right your digital ships in a turbulent sea of market transformation, the 2020 holidays are an existential test for both brands and retailers.

Here are my tips for how retailers, brands, and everyone else selling online can make the most of the 2020 holiday shopping season:

1. Retailers: be better than Amazon.

No one wants to sort through half a billion products to find a gift this season. Be better with curated lists of gifts that are tested and guaranteed by your reputation. Use the voice of your store and your retail associates to explain these products, their features, and their limits. Imagine your best floor associate selling to your online customer. Bring that experience to your digital channels.

2. Brands: enable your resellers with digital-first processes.

Resellers are focused on risk this season. Inventories will be low, and re-orders will be urgent. Brands must support the shift in reseller channels from instore to online. Brands must have automated self-service digital channels for content distribution, remix their product lines to emphasize the products sold most effectively online, and expose real-time delivery data to their resales channels to enable a responsive supply chain.

3. Everyone: differentiate online shopping experiences with content.

Once you have anted up to the online seller’s table with free shipping, free returns, and a competitive price, you need to differentiate with content. Overlay explanatory text onto product images, provide content that imparts to the shopper the knowledge they would gain from touching the product in a store. Deliver content that speaks with an authentic voice. 2020 has been an emotionally draining year. Make holiday shopping simple, honest, and easy.

Moody Nashawaty, Chief Strategy Officer @ MuteSix

Consumer spending is trending upward this Q4, but shoppers are still staying home. It’s too soon to say what long term effects the pandemic will have on retail, but the fact of the moment is that e-commerce is booming. 74% of U.S. consumers say they will shop online for the holidays. E-commerce revenue for Black Friday and Cyber Monday is projected to top $50 billion, and overall online sales this year will hit a trillion for the first time ever. It’s going to be all the more difficult for DTC brands to get ahead, but we’re optimistic about the opportunity for our clients to thrive.

Here’s what MuteSix is suggesting to prepare:

4. Stay away from complicated promotions.

Instead, use sitewide offers or spend more / get more tiered sales to keep campaign spending outside of the learning phase. Make sure to update all headlines and descriptions to include those promotions.

5. Clearly communicate deadlines and sales. 

Communicating early shipping deadlines should be the main focus in 2020. Use popup strategies and experience takeovers to share these essential deadlines as well as things like sales. It’s also a good idea to start BFCM early, but make people opt-in to trigger the onsite BFCM experience and get the promotions.

6. Double email and SMS sends for abandoned carts.

Many businesses send emails and text messages during this time, so you want to stay on top of inboxes. Generally speaking, doubling the number of emails and text messages you typically send would be ideal during the holidays.

7. Understand that your target demographic will look different.

Seasonal buyers are not the same as your standard customers because they are likely buying for someone else. Make sure you build lookalike audiences off of seasonal behavior and not just rely on purchase intent.

Alexis Ginsberg, Sr Manager, E-Commerce Performance Marketing @ Kate Spade New York

This holiday season will certainly be like no other. As marketers (and consumers) we need to prepare to execute flawlessly, move swiftly, and pivot seamlessly. The pandemic has only increased the bottom-line value and critical importance of digital media channels for brands, merchants, and vendors alike. Understanding and identifying opportunities and gaps in real-time, and reactively flexing strategy will be a key piece of driving growth and success this holiday season.

Here are a few more ways in which I’m approaching e-commerce and performance marketing strategy as we head into the holiday:

8. Target the right audience.

Identifying, learning, and assessing who your target audience and consumer is, how they behave, and what resonates with them is imperative for successful e-commerce, especially during the holiday season. I’ve helped lead extensive research on our current customer, her traits and characteristics, and how she shops, which has laid the groundwork and foundation for our ongoing and future audience approach.

Audience is also an important optimization lever. If a campaign, promotion, or message isn’t resonating, it’s time to tweak. Utilize your VIP or most important segments for lookalikes in search and social. This will empower you to leverage your existing customers to help prospect new ones.

9. Tailor content and offers to different types of holiday shoppers.

Tailor creative, messaging, promotions and site experience to each of your respective audiences. Lapsed customers may need a stronger incentive to come back to your brand, whereas active users may be enticed with a softer promo, like free shipping (which is almost the standard, especially during the holiday).

Feature higher price point items to your full-price shoppers, and consider pushing strong performing product categories to your sale or off-price shoppers, paired with an up-sell or cross-sell message to boost AOV.

On site, add badges to best-sellers, items low in stock, or markdowns to drive urgency and cart building. Highlight features like gift wrapping and gift cards to illustrate functionality and different ways and methods to shop, all contributing to conversion.

10. Continue testing during the holidays. 

While many may advocate against testing during the holiday shopping season, there are always opportunities to test in marketing and e-commerce.

Rotate in multiple creative variations to glean insights as to which performs the best, and the worst. Test adding new placements and partners to your media mix to diversify. Test new first, second, or third party audiences in line with your retention and CRM strategy. If feasible, look to test a new (or deeper) offer with select audiences. Test messaging around shipping cutoffs, features like curbside pickup, and in-store sales.

Test, test, test—both for real-time learnings and for the future. It’s never too early to start planning for next holiday!

Jon Nordmark, CEO and Co-Founder @ eBags and Iterate.ai

Covid has caused large organizations—as big as $60 billion in revenues—to turn on a dime. Opportunities can still be seized as consumers (and laws) favor frictionless checkout and online or mobile shopping. You still have time to digitize and optimize some of your experiences.

Thoughts for improvements:

11. Fine tune tools and processes for curbside pickup. 

Can you make curbside easier for store associates and customers? Can you make it easier for shoppers who turn off geolocation? Do you enable text messaging for your curbside shoppers?

12. Consider video consultations. 

We’ve been working with retailers that are using video consultations to help shoppers choose the right makeup and jewelry. This takes your store into people’s homes and personalizes the shopping experience.

13. Improve your online gifting technologies.

Gifting initiated online can be a lot more fun and rewarding today. Offer online unwrapping solutions. Allow gift recipients to change sizes or colors before a shipment is made.

14. Improve online experiences with third party tools.

Technologies that increase web speed are easy to install. Tech that includes “real AI” to improve recommendations and bundling is also easy to install. Many new technologies improve conversion rates. You should be constantly testing them and seeking incremental improvements.

15. Automate aspects of customer care.

As holiday shipment volumes increase, can you add some AI into your chat experiences? Maybe knock out one, two, or three use cases? Everything from shipment updates to reward number lookups can be handled by AI. This type of automation can increase responsiveness to customer inquiries and improves your Net Promoter Score while reducing costs.

16. Prepare for the future. 

Digital is expected to retain its market share gains (versus traditional shopping) even after Covid. Digital improvements you make today will pay long term dividends. So even if projects spill into 2021, push for upgraded curbside, more customized AI chat capabilities, touchless payments, new online shopping features, and adding virtual services to the products you sell.

Faisal Masud, Past Director @ Amazon and Staples, CEO @ Fabric

This holiday season, every day is going to be like Black Friday. We’re already seeing this with companies like The Home Depot extending Black Friday deals to the end of the year in an effort to reduce in-store crowding. What makes this even more interesting is that in-store deals will also be available online. So you could say every day this holiday season will be like Cyber Monday as well. Given the success of The Home Depot and other retailers extending Black Friday deals, it would be wise for other retailers to follow their lead.

Some other things to consider:

17. Manage cutoffs for Xmas delivery. 

Make sure there is clear communication on holiday delivery issues, especially since e-commerce has grown by double-digits in the last few months. Logistics will be a mess. Messaging is key.

18. Ensure excellent post-holiday return policies. 

Instead of thinking of returns as a cost, think of them as a way to better market your company and win sales over competitors. This will be a big differentiator, especially since more people will be shopping online.

19. Load test your sales channels.

Holiday shopping online will be off the charts. Make sure your website and other digital sales channels are ready for this never-before-seen spike in holiday traffic. Load test, optimize, and maintain core principles and scale via cloud environments.

20. Capitalize on less holiday travel.

There won’t be as much holiday travel this year so more people will spend money on gifts. For instance, upgrades will happen to home offices with better machines and hardware.

Samantha Coffey, E-Commerce Manager @ Pet Plate

This holiday season will certainly be different in many ways, but, fortunately for marketers, there are some best practices that will continue to ring true. For newly digitally-focused companies and digital ambassadors alike, below are some tips I’ve kept in my back pocket over the years that I expect to prove valuable during these socially distant Covid times.

Timeless best practices include:

21. Have a backup plan when it comes to creative.

Since sales are starting earlier and stretching longer, creative fatigue is real. To direct this challenge for digital ads, create multiple creative options now so content can be published in batches throughout the duration of your sale. This will also help you in the event that ads you had such high hopes for end up not performing well.

22. Drive urgency with copy.

If you don’t have resources to create multiple, high quality visual assets, play with copy instead. There are a million ways to say “this sale ends soon,” but only a handful of ways that actually inspire action. In addition to experimenting with plain text copy, experiment with text overlays on your visual assets.

23. Flex up referral programs.

During big sale moments like holiday deals, it’s easy for initiatives like referral programs to get overshadowed. A great way to keep your referrals program relevant this holiday season is by sweetening the deal there, too. During the holiday season when gifting is top of mind for consumers, referral programs are great tools to leverage and create deals for.

24. Partner with a like-minded brand.

Maybe this is a small addition to your product line, maybe this is a joint collaboration with a local charity, or maybe this is just really great shared content. Either way, partnerships are great for perpetuating brand excitement and potentially doubling your audience. Just make sure the collaboration is relevant. For instance, no one is asking for a SHELL x LEGO 2.0 collab this season.

Sean Sullivan, Digital Marketing Manager @ Parker Gwen

Physical retailers are in an adopt-or-die situation with digital commerce this year as many in-person businesses are either struggling or filing for bankruptcy. Yet Amazon has shown a huge Q3 revenue uptick and a very comfortable Prime Day in October. There’s no doubt that consumers will continue to shop online as we move into the holidays. At Parker Gwen, are focused on customer experience to succeed during this time and into the future.

Here’s how we’re preparing for the holiday season:

25. Focus on a few marketing channels.

Instead of scattering all your resources to many channels, figure out what your top two channels are and focus on those. Be sure to catch site visitors through email, SMS, and remarketing to remind them of abandoned carts and browse abandonments. Each nudge is crucial and reminds people to buy based on how they want to be communicated with.

26. Incentivize people throughout the whole buying process.

Great discounts and promotions will fly all around but consumers still review prices and reviews to get a good sense of the company. Rewards build great customer loyalty while building revenue and even company profit.

27. Make sure your attributable data makes sense.

Know who, where, and how people buy from you. Narrowing down on “clean” data will help make pivotal decisions when constantly tweaking your buyer personas.

28. Collaborate and iterate to win holiday sales.

For your business to succeed, communication and collaboration between, development, design, content, marketing, and customer support needs to be aligned. This will help you make quick changes and iterations to holiday strategy. Companies that are faster to adapt will win the sale.

Mark Wanczak, Director of E-Commerce @ StandDesk

Well, let’s just throw out the majority of what I’d typically recommend here and talk about what so many of us are facing over the next two months: how do we continue to quickly adapt to Covid’s impact to our typical holiday strategy in time for what will be the biggest e-commerce holiday season ever?

Here’s what we’re doing:

29. Start with your customers.

How has your customer base evolved over the past six months? Are they shopping a wider or narrower product set? How has your AOV and CVR changed? There’s a good chance the holiday buying season is only going to accelerate or emphasize these new trends in customer behavior.

30. Change traditions.

For us, a standing desk wasn’t exactly on the top of most people’s wish list in 2019. In 2020, we have an opportunity to give the learn-from-home students and work-from-home professionals something to ask for that can make a huge impact on their daily lives.

31. Simplify and iterate.

Don’t over-segment, over-target or over-think it. There is no perfect anything in 2020. Talk to your customers. Triangulate feedback with your data. Go live. Test and refine.

32. Don’t forget about New Year’s.

Everyone can’t wait to leave 2020 behind. Dollars will follow this desire.

Jordan Foutz, E-Commerce Marketing Manager @ SignalBoosters.com

This year has impacted everyone in ways that will be difficult to forget, but many online retailers will come out stronger and with more resolve than ever. Because of social distancing, the rules have changed for businesses and schools. Our company has new audiences and customers who now have to accommodate remote workforces and school districts’ requirements to provide distance learning options. Our products—cellular signal boosters—have been more in demand than ever before.

Through all of this year’s challenges, these are a few items that have helped us succeed and will help us make the most of the 2020 holiday shopping season:

33. Create content that answers pressing questions.

Our content team recently produced an article that helped us earn the number one position on Google for 8/10 top volume keywords in our industry. This resulted in traffic and sales that has significantly grown our business. We’ll be on the lookout for holiday-related topics to create content for.

34. Use consistent messaging across channels.

Our team recently closed a large deal over the phone due to an email campaign we had sent that same day. Our designer and developer worked quickly to revise our home page content to reflect the messaging in the email. This also increased homepage conversions by 59%. Look for opportunities to communicate deals across channels this holiday season.

35. Follow the quantitative and qualitative data.

We have a full-time analytics manager and UX designer on our marketing team who frequently review Google Analytics, Search Console, and heat maps. Using these tools and data to make smart, incremental changes has drastically improved our conversion rates this year, which will serve us well during holiday traffic spikes.

Liliana Molina, E-Commerce Manager @ Directed

Online retailers should prepare for a mega holiday season this year as Covid has significantly impacted consumers’ buying behaviors. Even with stores reopening and people getting more comfortable going outside, many of the new buying trends we have been seeing are expected to stick around.

One of the most significant changes in 2020 was the postponement of Amazon Prime Day to mid-October. While the delay of this major shopping event could negatively impact Cyber Week and the traditional holiday shopping season, you should still expect a tremendous Q4 for e-commerce.

To prepare for this, here are my tips:

36. Plan ahead for inventory. 

Make sure you have inventory available at all times. If you are on Amazon FBA, work with your warehouse or 3P logistic partner to have a plan B for FBM. As Amazon continues with delayed receiving times and re-stock restrictions, this will guarantee you are able to fulfill orders if Amazon can’t.

37. Refine your ad strategy and keyword targeting.

Use all the data you have collected during the past three months to refine your ad strategy. Also, identify your high converting products and optimize the listings. Look for less expensive keywords that have been converting well for those products and increase bids for those.

Elan Blitstein, eCommerce Manager @ CCJ

Unlike last year, people have already started holiday shopping because of the free time they’ve had on their hands while sitting at home under quarantine. This online shopping trend will soar even higher as the holidays approach. Amazon’s Prime Day that happened in October confirms this. Sales from Prime Day 2020 surpassed sales from Prime Day 2019 by 45.2%..

Here are some ways you can capitalize on this unprecedented holiday shopping season:

38. SEO your site for the holidays. 

People will be typing things like “best holiday gifts” and “best christmas deals” into search engines. You need to prepare for this by weaving holiday-related keywords into your page titles, page descriptions, and actual pages.

39. Experiment with influencer marketing. 

Instead of throwing all your money toward ads, experiment with influencer marketing on YouTube, Instagram, Pinterest, and other platforms. This can be a much more meaningful way of advertising during the holiday season when people crave connection with others.

40. Don’t forget about fulfillment and distribution.

After focusing on your marketing plan, make sure logistics are in order. Inventory should be full, especially with top sellers. Hire some local students who are studying online and looking to make some extra holiday cash to help with fulfillment this year. You should expect your sales volume to increase greatly. Prepare for the best.

Topics: Commerce
Robert Gibb

Tech advocate and lead editor @ fabric. Previously StackPath, Upkeep, StackShare, MaxCDN.

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