Why Holiday Shopping Season Actually Starts in September

The ROAD TO RICHES: What to Plan For in the Lead-Up to Black Friday & Cyber Monday

But DRM, Labor Day just ended. Why are you talking about holiday strategy?


During holiday 2018, shoppers spent $122 BILLION on e-commerce purchases, according to Internet Retailer. And the National Retail Federation estimates that online sales will grow by up to 12% in 2019.

You can’t afford not to plan your holiday strategy early.

The planning you start now will help set the foundation for a monumental revenue generating opportunity for your company — which in turn will set your brand up for a strong 2020.

Below, we’ve outlined the basic considerations you need to make, along with a rough timeframe for when you should make them. Because the key to a successful holiday season lies in doing your due diligence at the right time.

September: Lay Your Strategic Foundation & Critique Your Website

MVMT Watches Black Friday 2018 Email Marketing

The MVMT Watches email blast announcing 2018 Black Friday sale was sent on November 16, a full week in advance of Black Friday.

1. Make Strategic Decisions

By mid-September, you should actively be coordinating with your team at DRM about what you’re going to do for the holiday season, and how you’re going to do it. This includes the following:

  • Decide on the basic tenets of your holiday initiative. For most brands, this will be some sort of discount, such as 30% off sitewide. Other common ideas are a cart-builder discount, where the more consumers spend, the more they save (i.e. spend $100, get 20% off, spend $200, get 30% off, etc.).
  • Determine the length of time your promotion will run. E-commerce sales aren’t just for Cyber Monday any more. At this point, if you’re waiting for Thanksgiving to be over to run a promotion, you’re behind the curve. In 2018, some very prominent e-commerce outlets such as MVMT Watches launched their (very successful) Black Friday pushes at least an entire week prior to Black Friday.
    • Note that for some brands, waiting until the week of Black Friday to run a sale is far too late. Most sales during this period are in preparation for the December holidays, so if your product has a long lead or shipping time, then you may want to consider moving your promotion earlier in November and running it as a “pre-holiday sale.”
  • Develop your messaging. Coordinate with your team at DRM to get aligned on how you’re going to communicate about your promotion. You should be thinking about how to get your audience’s attention — it will be a crowded marketplace and you’ll need fresh, new creative. Yet your messaging should be clear, specific and straightforward. Now’s not the time to overcomplicate what you’re trying to sell.

2. Critique Your Website

Early September is the ideal time to do a conversion rate optimization audit on your site.

Conversion rate audits help spot usability issues with your site that might prevent users from completing a purchase. A member of your DRM team will likely reach out to you to discuss this further.

Toward the later part of the month, CPMs will begin to rise as brands begin to start their pre-holiday pushes.

Examples of successful Black Friday and Cyber Monday ads from 2018.


October: Finish Your Assets & Seed Your Funnel

  • By early October, your holiday creative assets should be well underway to ensure plenty of time to get them right. You should also be working on recommended site changes outlined in the usability audit.
  • By mid-October, you should be putting the finishing touches on your creative — now is not the time for last-minute changes. 
  • By the end of the month, your site changes should be fully wrapped up so you can properly prepare your customers for exciting opportunities coming up for the holidays.

Digital Marketing Experts Working Together

November: Execute Your Plan

It’s go time. Here’s your to-do list to ensure you’re able capitalize on this crucial money-making period.

  • Meet your KEY DEADLINE: November 1. DRM must have your ad creative by this date.
  • Finalize the specifics of your promotion. You and DRM need to be completely aligned on the what, when, where, why, and how of your campaign.
  • Make sure your inventory matches your goals. If you run out of stock, you’ll miss out on money — and you’ll damage your relationship with your customers.
  • Confirm with your bank that you have plenty of room on your credit card that’s being used for your digital marketing. Nothing kills holiday sale momentum faster than ads being shut off because the credit card Facebook or Google is using has hit its limit.
  • Allocate a “best-case-scenario” budget. If things go according to plan, there will be massive opportunity for you to scale up your campaigns — and thus your revenue.

Once you’ve got all this done, you’re ready to nail your Black Friday / Cyber Monday strategy.

Ecommerce Marketer Scanning A Box for Shipping

December: Know What to Expect Post-Sale

After Cyber Monday, there’s always a temporary lull. This is totally normal. DRM is ready and available to help you capitalize on any revenue-making opportunities between now and the end of the year — and well into 2020 — but this is a good time to focus on the amazing sales you’ve already made:

  • Get your items shipped in a timely manner. Your customers are buying gifts and it’s important they arrive when promised (or even a little earlier than expected). You’ll build brand loyalty — and customers may be so happy with their purchase that they’ll buy again before the season is over.
  • Make sure your customer support team is ready to help. Now’s the time to really demonstrate your professionalism and turn one-time leads into long-term customers.
  • Be prepared to pivot. DRM has a lot of experience in successful holiday promotions, and we may make recommendations that need to be acted on quickly.

If you’re ready to act in September, you’ll be more than ready for 2020, thanks to your strong holiday sales.

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