Wonderly’s 2024 Holiday Planning Guide


October 28, 2024

Every year, we hit October and the holidays come into focus!

Below, we wanted to share Wonderly’s guidance to brands who are brainstorming what they’ll be doing over the holidays. We’re including a rough timeline for you to consider and make your own, an explainer on the principles behind that timeline, and a checklist of creative and marketing systems needed to execute your holiday campaigns well!

Again, these are templates and suggestions! If it makes more sense for your brand to lay low or do an anti-campaign during the holidays, go for it!

If the principles are helpful and you can execute on your own, that’s great! If you need some help brainstorming, planning, or executing over the holidays… just say the word and we’d love to help.

Strategic Holiday Promotion Breakdown

1. Focus on Audience Growth Before Sales (October-Early November)

  • Objective: Build a strong foundation by growing your audience ahead of the holiday rush. Running a giveaway or list-building campaign can rapidly increase your email list and social media followers.
  • Why: Newer followers or subscribers are often more engaged early on, and they are more likely to convert during the first stages of their relationship with your brand.

2. Prioritize High-Lifetime-Value Customers Before Big Sales (Mid-November)

  • Objective: Run exclusive promotions targeting your top 20%-40% of customers. These high-value customers should be offered bundles, memberships, or gift card deals that add long-term value, rather than turning them into holiday discount shoppers.
  • Why: Encouraging top customers to “top off” their relationship with you helps increase their LTV while maintaining their loyalty without discounting your premium offers.

3. Black Friday/Cyber Monday for Discount Shoppers and New Customers (Late November)

  • Objective: Focus on attracting bargain shoppers and first-time customers with highly visible discounts and promotional deals. This is an opportunity to convert new customers during the peak of holiday shopping.
  • Why: Black Friday and Cyber Monday are great for driving sales volume and acquiring new customers. Use this phase to target those who are looking for deals and special offers.

4. Maximize Sales Through Gift Cards (December)

  • Objective: Offer gift card promotions that encourage last-minute shoppers and existing customers to purchase, especially when they are unsure of what to buy. Gift cards are a great tool to extend the holiday season into January.
  • Why: Gift cards work well during the late holiday season and can help boost sales even after the main promotional events are over.


Promotion Timeline Example

Late October – Early November (Oct 21 – Nov 7):

Campaign Type: Giveaway or List-Building Campaign
Goal: Build audience by increasing email opt-ins and social followers.

Mid-November (Nov 15 – Nov 21):

Campaign Type: VIP or Loyalty Promotion (Target top 20%-40% of customers)
Goal: Increase customer lifetime value (LTV) through bundles, memberships, or gift card incentives.

Late November (Nov 28 – Dec 2):

Campaign Type: Black Friday/Cyber Monday Deals
Goal: Acquire new customers through discount-focused promotions

December (Dec 3 – Dec 31):

Campaign Type: Gift Card Promotion
Goal: Maximize gift card sales, catering to both existing and new customers.

Holiday Promotion Checklist with Estimated Timelines

1. Landing Page Development

  • Design & Wireframes: Create landing pages tailored to each promotion (giveaway, VIP promotion, Black Friday, etc.). Ensure each page is optimized for mobile and SEO.
    • Deadline: By October 15
  • Content Creation: Ensure messaging, copy, and imagery align with each specific campaign.
    • Deadline: October 20
  • A/B Testing Setup: Prepare variants for landing page testing to improve conversion rates.
    • Deadline: Ongoing throughout October-November
  • Tracking Setup: Ensure tracking for email opt-ins, user behavior, and conversions (Google Analytics, Facebook Pixel, etc.).
    • Deadline: October 20

2. Functionality to Execute Discounts

  • Discount Code Setup: Implement discount codes with specific parameters (e.g., minimum spend, percentage off, bundles).
    • Deadline: November 10
  • Integration: Ensure discounts are properly integrated with your eCommerce system (Shopify, WooCommerce, etc.).
    • Deadline: November 10
  • Cart and Checkout Optimization: Ensure smooth functionality and user experience during checkout, with applied discounts.
    • Deadline: November 15
  • Countdown Timers: Add urgency with countdown timers for promotions (Black Friday, Cyber Monday).
    • Deadline: November 15

3. Customer List Segmentation

  • Segment High-Value Customers: Create specific segments for your top 20%-40% of customers for personalized promotions.
    • Deadline: November 5
  • Email List Segmentation: Segment your email list based on recent opt-ins, high spenders, and previous holiday shoppers.
    • Deadline: November 5
  • Dynamic Personalization: Set up personalized emails and landing pages based on segmentation.
    • Deadline: November 10

4. Site Updates and Clear Timelines

  • Pre-Holiday Site Refresh: Ensure your website is updated with holiday branding (banners, pop-ups, etc.).
    • Deadline: October 20
  • Campaign Launch Updates: Coordinate the launch of promotions on the site (giveaways, early VIP access, Black Friday/Cyber Monday deals).
    • Deadlines:
    • Giveaway: By October 21
    • VIP Promotion: By November 15
    • Black Friday Deals: By November 28
  • Product Updates: Ensure all gift cards, bundles, and promotions are live and visible on the site.
    • Deadline: November 20

5. Sub-brands for Campaigns

  • Design Sub-Brand Assets: Develop sub-brand visuals (logos, colors) for different campaigns (e.g., VIP vs. Discount shopper campaigns).
    • Deadline: October 25
  • Brand Consistency: Ensure sub-brands align with overall brand identity but provide enough distinction to highlight different promotions.
    • Deadline: Ongoing with each campaign launch

6. Paid Ad Creative

  • Creative Asset Production: Design paid ad visuals for each phase of the promotion (giveaway, VIP promotion, Black Friday, etc.).
    • Deadline: October 15 for early campaigns
    • November 10 for Black Friday/Cyber Monday assets
  • Copywriting for Ads: Develop targeted ad copy for different audience segments.
    • Deadline: October 15 for early campaigns
    • November 10 for Black Friday/Cyber Monday ads
  • Ad Tracking: Set up tracking links and conversion tracking for paid ads.
    • Deadline: October 20

7. Budget Allocation

  • Budget for Paid Ads: Define budgets for each campaign phase (list-building, VIP promotion, Black Friday/Cyber Monday).
    • Deadline: By October 10
  • Discount and Promotion Costs: Set aside budget for expected discount losses (e.g., percentage off, free shipping).
    • Deadline: By November 1
  • Ad Spend Strategy: Plan ad spend allocation across different platforms (Google, Facebook, Instagram, etc.).
    • Deadline: By November 1

Maximize Your Holiday Success with a Thoughtful, Timely Strategy

The holiday season presents a tremendous opportunity to engage your audience, attract new customers, and boost revenue. However, the key to maximizing this potential lies in careful planning, segmentation, and timely execution. By developing a phased approach that caters to both high-value customers and first-time buyers, and by implementing the right design, functionality, and promotional tools, you can create a seamless shopping experience that drives results.

Remember, the earlier you start building your list, designing your campaigns, and preparing your website, the more prepared you’ll be to capitalize on the busiest shopping time of the year. A strategic, well-executed holiday promotion can not only increase sales in the short term but also lay the groundwork for stronger customer relationships and brand loyalty moving forward.

Now is the time to put your plans into action — ensure that your website, customer segments, and promotional tactics are aligned with your business goals, and get ready to make this holiday season your most successful yet.