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3 Part Holiday Sales Challenge

October 13, 20 & 27, 2026 | 2 hours each session

11am- 1pm

The holiday shopping season is one of the biggest sales opportunities of the year—but waiting until Black Friday to decide what you're going to offer is already too late.

The Holiday Sales Challenge is a three-part, hands-on series designed to help small business owners build their holiday promotions, get them in front of customers, and create a plan for turning holiday attention into actual sales.

We'll explore the different ways you can promote your business during the holiday season—from social media, email, and special offers to local outreach, partnerships, events, contests, gift ideas, and more. Then you'll choose what makes sense for your business and start building it.

This isn't three classes about holiday marketing.

You're going to create your holiday sales plan and start putting it into motion.

Between sessions, you'll take action. When we come back together, we'll look at what happened, build your follow-up strategy, make adjustments, and plan your next move.

By the end of the challenge, you'll have a holiday promotion plan you can actually execute throughout November and December.

You'll Learn How To

Identify the biggest holiday sales opportunities for your business
Choose the right promotional channels for your customers, including social media, email, local outreach, partnerships, events, referrals, and contests
Create a holiday offer or promotion that gives customers a reason to buy
Plan around important holiday shopping dates without trying to participate in everything
Build anticipation before your promotion launches
Decide when and how often to promote your offer
Create a simple follow-up sequence instead of relying on one post or email
Extend promotions and follow up with interested customers
Track what's working and adjust while there's still time
Turn holiday customers into opportunities for repeat business after the season ends

How the Challenge Works

Part 1: Build Your Holiday Promotion

October 13

We start with the opportunity.

We'll explore different ways small businesses can generate holiday sales, including promotions, bundles, gift cards, limited-time offers, events, collaborations, contests, local outreach, email, and social media.

Then you'll choose your strategy.

You'll identify who you're trying to reach, what you're going to offer, where you'll promote it, and the first steps required to get it moving.

You'll leave with the foundation of your holiday sales campaign and clear actions to complete before Part 2.

Part 2: Timing, Promotion + Follow-Up

October 20

A holiday promotion isn't one post.

In Part 2, we'll build the rhythm around your campaign: when to start talking about it, how often to promote it, how to build anticipation, and what to do when someone shows interest but doesn't buy.

We'll create a simple promotional and follow-up sequence you can use across email, social media, direct outreach, or wherever your customers are.

We'll also look at what happened after Part 1 so you can make adjustments before the busiest part of the season begins.

You'll leave knowing what you're saying, where you're saying it, and when.

Part 3: Your Holiday Sales Game Plan

October 27

Now we put the entire season together.

We'll review what's already working, troubleshoot what's not, and map out your next steps for November and December.

You'll decide which promotions to continue, what needs to change, and where to focus your time during the busiest weeks of the holiday season.

We'll also look beyond the initial sale: follow-up, repeat purchases, referrals, and ways to stay connected with the customers you gain during the holidays.

You'll leave with a clear sales plan for the rest of the holiday season.

Who It's For

This challenge is for small business owners who have something to sell during the holiday season and want a clear plan for promoting it.

You may sell products, services, experiences, gift cards, packages, or something that could be turned into a holiday offer.

You may already have holiday promotion ideas but haven't organized them yet. Or you may have no idea what your holiday offer should be.

Either way, the goal is the same:

Stop waiting until the holidays arrive to start selling for them.

Outcomes

By the end of the three-part challenge, participants will:

✅ Create a holiday offer or promotional strategy

✅ Choose the sales and marketing channels they'll use

✅ Begin putting their holiday campaign into motion

✅ Build a promotional and follow-up sequence

✅ Map out key sales activities for November and December

✅ Know what to track and how to adjust based on customer response

✅ Have a clear plan for turning holiday activity into continued sales

The holiday season moves fast. Your marketing should already be moving before it arrives.