When To Prepare and Launch Retail Holiday Marketing, Plus Other Strategies [Infographic]

By: on January 6, 2020

With the 2019 holiday season barely in hindsight, you might be thinking it’s too early to begin putting together your 2020 seasonal retail marketing calendar.

But, there’s no such thing as being too prepared for the holidays—especially when, according to our 2019 holiday survey, more than 95% of retailers say their store is either “somewhat prepared” or “very prepared” for the retail holiday season.

Below, we’ll examine the results of a survey we ran of U.S. retailers. Our findings will help inform your planned investment in terms of time, budget, and human resources for the year.

How to plan effective holiday promotions in 2020

3 takeaways

1. Set aside the largest portions of your holiday budget and resources for Christmas and Black Friday

Allocate the most monetary and human resources toward key retail holidays. Christmas is the number one holiday that retailers invest in, followed by Black Friday, Cyber Monday, and Mother’s Day.

2. Prepare for end-of-year holiday promotions no later than October

For a headstart on your competition, get the ball rolling as early as May and no later than October. For big retail holidays like Christmas, that means starting your preparations as early as six months in advance. For smaller holidays like Mother’s Day, we recommend a three-month jumpstart.

3. Launch your end-of-year promotions no later than November

Timing matters. Nearly half of retailers launch their holiday promotions between October and November. Starting promotions too early or too late can lead to fewer sales than expected. Depending on your product and customer base, aim to launch your promotions by November at the latest.

Your retail seasonal planning calendar 2020

Don’t leave preparation to the last minute. Start by knowing your key retail dates for 2020.

Key Holidays in 2020


Jan. 1: New Year’s Day
Jan. 25: Chinese New Year


Feb. 2: Super Bowl Sunday
Feb. 6: New York Fashion Week
Feb. 14: Valentine’s Day


March 17: St. Patrick’s Day


April 12: Easter Sunday


May 5: Cinco de Mayo
May 10: Mother’s Day


June 21: Father’s Day


July 13: Amazon Prime Day


Aug. 9: Women’s Day


Sep. 29: Back to School


Oct. 31: Halloween


Nov. 11: Veterans Day

Nov. 11: Singles’ Day

Nov. 26: Thanksgiving Day

Nov. 27: Black Friday

Nov. 28: Small Business Saturday

Nov. 30: Cyber Monday


Dec. 5: Small Business Saturday

Dec. 25: Christmas Day

Dec. 31: New Year’s Eve

What you need to plan for your retail seasonal holidays

Inventory planning

Ensuring you have enough inventory (not insufficient or excess amounts) to meet customer demand is key during highly competitive retail holiday events.

  • Research historical data and buying trends: What categories sold well at this time last year? Learn what your strengths and weaknesses are and then come up with initiatives to fill those gaps, such as launching a social media or email marketing campaign.
  • Track current data: One of the best ways to prepare for the next holiday season is to track and report on your busiest times. To do that, invest in tools to track your point of sale (POS) data, foot traffic, and website.
  • Forecast demand and determine when items are needed: Are your Mother’s Day items needed a week or two before the actual day? Include all that information in your planning so that you can be prepared for the items’ arrival, as well as how many days items should be on the shelves.

Sales and discount planning

Knowing when and how to execute promotional strategies can make or break your holiday promotions.

  • Check for discounts and promotions with suppliers: It never hurts to ask. Are pre-sale promotions or discounts available for orders? Will there be any changes to shipping and pricing during peak holiday times? You will want to make sure there are no surprises when it comes to your inventory and sales during this time.
  • Monitor sales during the holiday events: This is a no-brainer, but keep an eye on your sales during promotions or reorders to understand customer demand (or lack thereof). Decide what level of sales volume will trigger promotions or reorders.
  • Know what sales, discounts, and promotions you’ll run: Whether you’ll be discounting your best-sellers or running a “buy one, get one free” promotion, make sure you have your strategies in place for driving sales.
And lastly, prepare your team for the anticipated holiday demand through seasonal hiring.

Next steps

  • If you don’t already have a system in place, visit our retail POS system software page and filter by retail type, number of stores, price, and rating to determine what software suits your needs best.
  • Looking for an inventory system to integrate with your POS? Or want to have a more in-depth conversation about what software can help you the most? Whatever it is, our team of software experts are available on live chat or you can make an appointment for a free 15-minute consultation to answer any questions you have about how your POS or inventory management system can help you plan for your next retail holiday event.

You may also like:

Why Your Business Should Start Offering Gift Cards Now

3 Proven Ways to Drive Gift Card Sales and Increase Your Profit

3 Retail Holiday Promotion Ideas to Win Big This Season

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