Preparing for the Holidays! Seller Community Holiday Guide 2018

The holidays are coming! To help you prepare we asked members of the Seller Community to share their top tips for planning for the holiday sales season. These sellers provided tips on special offers, holiday staffing, seasonal marketing campaigns, gift cards — and even how to make the most of quiet days if the holidays are your slow season.


We’d also love to hear your planning tips and see any pictures of your business in the lead up to the holidays. Feel free to reply with your tips and photos at the end of this post. Is this your first year using Square Gift Cards? Let us know! Is this your first year accepting payments online? Tell us all about it!  


If you have any questions for another seller just @mention them in your reply!


The fine print: Comments have been lightly edited for clarity and/or length.




Q&A with @DaoDeJing, Escapade


Want to make the most of sales during the holidays but not sure where to start? Travis, aka @DaoDeJing, who runs a group entertainment venue has some great advice about staying focused on one new product or service as you jump in to holiday sales.  


Who are you and what type of business do you own?

My name is Travis, and I own and operate an interactive group entertainment venue (escape rooms, murder mystery dinners, haunted houses, etc.). The business also has a small retail merchandise side.


What is the best practice you put in place to prepare for the holiday season?

The best thing I can do to make the holidays productive is to prepare a brand new service and debut it about a month before the holidays begin.


I do offer a few "door buster" deals on Black Friday, but these are just 2 or 3 specific items with broad appeal, mostly just for the purpose of having an excuse to have an ad to get people's attention.


In addition to a Black Friday sale, I will release email and social media ads in the week before Thanksgiving and the week before Christmas. Each ad will also mention gift cards. I've noticed that gift card sales don't necessarily take off until just the final week before Christmas, so if it appears they're not selling well just wait!


How do you go about choosing how to implement your best practices?

Basically just based off of what methods have worked well for me in the past. Generic ads and generic emails tend not to get a worthwhile response unless they are targeting a specific date or offering a specific product.

Q&A with @ryanwanner, R&R Coffee Cafe and Golden Pine Coffee Roasters

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@ryanwanner is a cafe owner and coffee roaster in Colorado. For his business, the holidays are a great opportunity to market a limited edition product and to boost sales for items that are popular during this time of year (pies!).


Who are you and what type of business do you own?

My name is Ryan Wanner, I own R&R Coffee Cafe and Golden Pine Coffee Roasters in Black Forest, Colorado--just a little ways north of Colorado Springs. We are a from-scratch bakery, craft coffee roaster, and we feature locally sourced breakfasts and lunches. We have been in business now for over 10 years.


Do you tend to promote any specials during the holiday season? What are they?

We primarily focus on add-on sales to drive the higher volume. I have pie order cards on the tables of our cafe by early October, and I usually utilize Square's Marketing to push reminders about pies in early November. Once Thanksgiving is over, I focus on explaining how bagged coffee is a perfect stocking stuffer (you only need to buy one thing to fill the stocking! :), and bake-at-home cinnamon rolls and sticky buns. Again, table talkers are out on the tables and Square Marketing drives the point home.


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Do you have any special holiday marketing campaigns planned? How do you go about choosing how to implement them?  

Sticking with the tried and true again this year! We promote our completely from-scratch pies and cakes via table talkers, posts on Facebook, Twitter, and Instagram, reminders at the register (including bottom-of-receipt notes), and Square's Marketing program. We do the same for our coffees and bake-at-home goodies for Christmastime. Every year, we also create a special Holiday Blend coffee, which is limited to roughly 300 pounds. Once it's sold out (Last year it was sold out 4 weeks after I launched it!) that's it for the season. Having the Limited Time Offer definitely helps drive the sales.



️Lightning Tips

We also asked the Seller Community to share their best piece of advice when preparing for the holiday season. They’ve shared great tips about managing staff, promoting your business and even how to make the most of the holidays if it’s actually a slow season for you!


“Hire extra seasonal employees and have more on staff and on schedule than you think you need - people will have last minute vacation plans and people will get sick.” @pessosices, Pessos Ices and Ice Cream


“Your employees are working hard for you.  Bringing in food on the weekends when you are the busiest is a good morale booster, keeps your employees in the store.”

@RHatch, Kermit’s Super Wash


“Advertise all your specials on Social Media like Facebook, Twitter, etc. Push Gift Cards - they are always great sellers especially around the holidays. Advertise your Gift Cards early so people think of you when they need some. Square Gift Cards have made our selling season so easy.”

@Ron, JR’s Fresh Cut Fries


“Sending out postcards about 3-6 months in advance of the holidays ensures that guests do not forget to reserve our popular family and friends reunion home, the Tudor Rose Manor at the Rio del Mar beach in the Santa Cruz CA area. It sleeps up to 22 guests in 9 sleeping areas and it takes time to organize a large group!”

@BeachRental, Tudor Rose Manor Vacation Rental


A large percentage of my business is handmade items, so creating holiday-themed items all year is essential. I might be sitting outside enjoying the Summer sun, but I'm cutting paper or drawing out new designs for Christmas. The holiday season is so concentrated with sales, there is not enough "making" time unless you utilize the entire year!”

@HC_Charlie, Homestyle Charlie


“During my slow season, I also try to attend as many local events as possible. Finally, I donate leftover stock that I won't be able to sell to local charities or homeless shelters. This gives you good press and people are more likely to purchase from a caring, small business than a greedy one.”

@Crazyyarnmomma, B Stitches Gallery


“When it's busy, it's hard to take a step back. Taking a closer look at the data of what you're selling can help revitalize your business. Take the time to re-evaluate what's the most cost effective, what's selling and what's not, and see if you have any room to simplify and improve your offerings. Whether it's cutting down on some menu items, simplifying sizes, tweaking prices, or maybe starting that new product line you've been dreaming of, now's a great time!”

@pessosices, Pessos Ices and Ice Cream


“People like to be appreciated and we feel you should always show your gratitude towards customers. Ask if there is anything they would like to see in your store or ways they think you can improve - I mean our customers are what keeps us going.” Karla, @KMadison, Madison Corner Gifts


Want More Tips?


Check out a few of our resources below.


Looking forward to hearing your number one tip when getting ready for the holiday season. Click Reply below to comment!

Message 1 of 34
1 Best Answer
Super Seller Alumni

Best Answer

So many great tips! Thanks so much for putting this together!

Pesso - he/him
Pesso's Ices & Ice Cream
Square Super Seller - I'm here to help!

View Best Answer >

Message 2 of 34
Super Seller Alumni

Best Answer

So many great tips! Thanks so much for putting this together!

Pesso - he/him
Pesso's Ices & Ice Cream
Square Super Seller - I'm here to help!
Message 2 of 34

Great tips, thank you for that! A question that always comes up for us though is which holidays are baning holidays for you and which one's are not? Do you have a list of the holidays where depsits will be postponed during this season?




Kyle D Eisenberg

Golden Gate Mobile Notary & Apostille

Phone: [redacted]

Web: www.goldengatenotary.net 

Email: [redacted]

Message 3 of 34

Hi Kyle, 


Thanks for the question! Deposits may be delayed around any major bank holiday since when you see your funds in your account is largely dependent on your bank's processing times. 


For the rest of the year, these are the official bank holidays: 

  • Veterans Day: Monday, November 12
  • Thanksgiving Day: Thursday, November 22
  • Christmas Day: Tuesday, December 25
  • New Year's Day: Tuesday, January 1 

If we anticipate any other delays to deposits, we'll make sure to post in the community so you know about it. Thanks again, @GGMobileNotary

Message 4 of 34

This list helped us throughout the holiday season, thank you



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Message 10 of 34
Square Community Moderator

Thanks for the kudos, @sell-my-phone! Feel free to reach out if anything comes up or if you have specific questions. We are here to help!

Community Moderator, Square
Sign in and click Mark as Best Answer if my reply answers your question.
Message 11 of 34

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Message 13 of 34

Thanks for sharing this post. Great read.

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Message 15 of 34

As a young business in a new location and trying to establish myself, this list is ever so helpful!  I especially like the idea of focusing on one or two things during the Holiday season.

Thank you!

Knot Just Yarn, LLC

Sheila @ Knot Just Yarn, LLC
Message 16 of 34

Hi! Thank you for sharing this article. This will help me in starting my new business. 


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This is such an interesting article. Thank you for sharing.



Message 18 of 34

This is so helpful especially now that i'm starting my business. Thank you!




Message 19 of 34

I find this article very helpful especially holiday seasons is already approaching. 

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Message 20 of 34

Thank you for sharing these ideas, will definitely save this for the next holiday. Mobile Notary Miami South Florida

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