Holiday Sales on Autopilot: 7 Retail Automations to Set Up for 2025

Key Takeaway:

Learn 7 automations you should set up now for a less stressful and more streamlined 2025 holiday sales season.

The holiday season is retail’s biggest opportunity—and your busiest. Between launching promotions, managing inventory, and answering a flood of customer questions, it’s easy to feel overwhelmed. That’s why automation is your secret weapon in 2025.

Today’s tools go beyond email, streamlining your entire holiday operation – from abandoned carts and back-in-stock alerts to chatbots and loyalty rewards. With shoppers expecting personalized, real-time experiences, automations don’t just save time; they boost conversions.

Ready to make your marketing smarter, your team more efficient, and your customers happier? Here are seven retail automations to prioritize this season.

1. Email & SMS Marketing Automations

Email automation remains one of the highest ROI channels in retail marketing, and when paired with SMS, it becomes even more powerful. Automated emails had 52% higher open rates and 2,361% better conversion rates than regular scheduled campaigns, as Omnisend data confirms.

Meanwhile, SMS continues to rise as a preferred channel for real-time updates and promotions. According to Campaign Monitor, text campaigns have a 98% open rate. It’s also particularly effective during flash sales, back-in-stock alerts, and last-minute gift pushes—where speed and immediacy make a big difference.

Automations to set up ASAP:

• Holiday Welcome Series
• Abandoned Cart + Browse Abandonment
• Holiday Gift Guide Announcements
• Shipping Deadline Reminders (SMS)
• Thank You / Post-Purchase Follow-Ups

2. Customer Segmentation & Personalization

Retailers that personalize their marketing see higher revenue and retention, and AI is making it easier than ever. With tools like Klaviyo* and Shopify, you can automatically segment customers based on behavior, location, purchase history, and even holiday intent (gift-giver vs. self-shopper).

AI-assisted segmentation also enables dynamic content blocks, so shoppers see personalized product recommendations and copy based on who they are and what they love.

Segment examples for holiday targeting:

• VIP Customers (early access offers)
• New vs. Returning Buyers
• Gift Shoppers (buying for others)
• Discount-Responsive Shoppers
• Last-Minute Buyers

3. Inventory & Back-in-Stock Notifications

Out-of-stock doesn’t have to mean missed opportunity. With automated “notify me” flows, you can collect customer interest and instantly alert them when products are available again.

Shopify users can integrate back-in-stock notifications directly into product pages. When paired with Klaviyo, this trigger can fire an email or SMS campaign the moment the item returns (no manual work needed!). Per Omnisend, back-in-stock emails achieve a 59.19% open rate and a 5.34% conversion rate.

Why it matters: Shoppers are often ready to buy but hesitant to check back. A single timely message can convert a lost sale into a loyal customer.

4. Chatbots & AI-Powered Live Chat

AI chatbots aren’t just answering questions, they’re closing sales—especially with millennial and Gen Z shoppers who rely on AI tools to help them gift shop for loved ones. According to recent data from Adobe Analytics, traffic generated by AI-powered chatbots increased by 1,300% over the 2024 holiday season.

Today’s holiday shoppers expect fast responses, especially during high-stress gifting periods. Automating your most common FAQs with a chatbot frees up your staff and ensures shoppers don’t bounce from frustration.

Smart chatbot uses for the holidays:

• Personalized gift finder tools
• Shipping cutoff countdowns
• Gift wrap and return policy FAQs
• Cart reminders with embedded checkout links

5. Abandoned Checkout Recovery

Cart abandonment is one of the most costly leaks in the ecommerce funnel – but also one of the most fixable. According to Omnisend data, abandoned cart emails achieve a 42.02% click-to-conversion rate. For every three people who clicked on one of those “abandoned cart” emails, one of them went back and bought the item.

Go beyond email by adding popups, SMS reminders, and discount incentives. For instance, Shopify’s built-in abandoned checkout automation lets you trigger these flows without complex setup.

Optimize with:

• Tiered messaging (based on cart value)
• Time-based nudges (e.g., 1 hour, 24 hours later)
• Personalized product mentions and images

6. Order & Fulfillment Updates

Once the order is placed, the experience is just beginning. Automated confirmation emails, shipping updates, and delivery alerts build trust and reduce support load.

Shopify* enables these notifications natively. And platforms like Zapier can help you automate even more across systems – like syncing orders with your warehouse or POS, triggering inventory updates, or sending tracking numbers via SMS.

Ideas to enhance fulfillment comms:

• Add product care tips or return info to order confirmation
• Offer a “you may also like” recommendation in the shipping email
• Celebrate delivery with a surprise discount or loyalty points

7. Review Requests & Loyalty Automations

The post-purchase moment is your chance to keep the conversation going. Automate review requests to trigger 5–10 days after delivery, while the excitement is still high. Automated review requests typically generate higher response rates than manual outreach.

Pair this with loyalty automations to reward repeat purchases, referrals, and reviews themselves. Offer bonus points or early access to New Year collections. And don’t forget to showcase the social proof you collect, especially user-generated content (UGC).

Ready to Automate Your Holiday Season?

Let the TTG team help you design your flows and select the right platforms.

Schedule a Strategy Session Now

*Disclosure: Links included in this article might be affiliate links. If you purchase a product or service with the links that we provide, TTG may receive a small commission. There is no additional charge to you!