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From One-Time Shoppers to Lifelong Subscribers: 6 Post-Holiday Retention Strategies for Subscription Businesses

  • Regina Mae Ongkiko
  • Oct 26, 2023
  • LTVplus

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The holiday season is a pivotal time for subscription businesses. With Black Friday, Cyber Monday, and the Q4 shopping frenzy, e-commerce brands and subscription businesses are ready for the surge of shoppers.

During this period, shoppers are ready, willing, and able to spend. This results in businesses getting an influx of new customers. While this is very exciting, it also presents a challenge: How can these holiday shoppers be converted into loyal, lifelong subscribers?

What’s the Deal with Holiday Retention?

In e-commerce, the holiday season is basically the Super Bowl for retail businesses. To put the scale of this shopping extravaganza into perspective, consider the record-breaking Black Friday Cyber Monday (BFCM) weekend in 2022. 

According to Adobe Analytics:

  • Black Friday online spending hit $9.1 billion, beating 2021’s record by 2.3%. 
  • Cyber Monday generated $11.3 billion in online sales

There’s no doubt about it — the Q4 holiday season is the busiest and most lucrative time for online businesses. 

Due to the hustle and bustle of the holiday season, businesses prioritize acquisition over customer retention. However, retaining customers is critical for long-term growth. 

After all, customer retention is the life and blood of subscription businesses.

6 Post-Holiday Retention Strategies to Keep the Momentum 

After the holiday rush, maintaining momentum and nurturing new customer relationships is important. Here are several strategic approaches to ensure that your post-holiday customers transition into loyal, long-term subscribers:

Offer incentives for long-term commitment

One effective strategy to keep the momentum going is to offer incentives or perks that will encourage your new subscribers to continue with their subscriptions. These incentives can actually come in various forms — discounts, exclusive offers, or even upgrades. Encourage your new subscribers to stay loyal by providing added value in exchange. 

Here are some ideas to explore:

  • Create tiered subscription plans with more valuable benefits for long-term commitments.
  • Offer discounts or special promotions for subscribers who commit to annual plans.
  • Implement referral programs that reward both the referring customer and the new subscriber.


  • In this example from ClickUp’s pricing plans, the annual subscription fee is $3 less than the monthly one.

Implement subscription flexibility and customization options

Today’s consumers appreciate flexibility and personalization. In fact, in a report by, more than 22% of consumers shared that convenience is their top reason for subscribing. They will gladly cancel if the merchants don’t offer the convenience that they expect. 

Additionally, when respondents were asked why they would cancel a subscription, 27% mentioned the inability to pause or skip and 23% cited being unable to change subscription frequency. 

The same study showed that, on average, 68% of subscription businesses offer a variety of plans. However, it also reported that less than half (46%) allow subscribers to update or modify their plans. 

Providing options for subscribers to customize their subscriptions based on their preferences not only enhances the customer experience but also increases the likelihood that they will stick around.

Here are some ideas on how you can inject flexibility and personalization:

  • Offer subscription tiers with different levels of customization and flexibility.
  • Allow subscribers to modify their subscription frequency, product choices, or delivery schedules.
  • Continuously gather feedback to understand subscribers’ preferences so you can adapt accordingly.


For Pet Circle, customers can choose a product, and then choose the delivery schedule—anything between one to 26 weeks.

Launch a new campaign in January

It’s essential to keep the excitement alive by launching a new marketing campaign in January. 

This can help transition the holiday shopping enthusiasm into a year-round engagement strategy. A well-planned January campaign can re-engage post-holiday customers and remind them of the value that your subscription offers.

Some tips on how to execute January campaigns:

  • Develop a thematic January campaign that aligns with customer interests or resolutions.
  • Highlight any new products, features, or benefits that subscribers can enjoy in the new year.
  • Use personalized email marketing to reach out to post-holiday customers and invite them to participate in the campaign.


Yohana offers personalized help for family and home tasks at $129/month. Their New Year email makes their subscribers think ahead for the year and then offers them an annual plan for $999. 

Launch a customer loyalty program

A well-executed customer loyalty program can significantly enhance retention. Such programs reward customers for their ongoing support, so they help foster a sense of loyalty and belonging. 

In fact, loyalty programs help make 60% of shoppers more loyal to a brand.

Here are some ideas for your loyalty program:

  • Design a loyalty program with clear rewards and achievable milestones.
  • Promote the program to your subscriber base and explain its benefits.
  • Ensure that the program is easy to join and that customers can track their progress.
  • Loyalty programs can include point systems, exclusive perks, and early access to promotions.
  • Adopt a point-based system where subscribers get higher-value rewards for more points. Points can be earned from purchasing add-ons to their subscriptions or even by tying in a referral program.


CVS Pharmacy has a free loyalty program, yet they also have a subscription loyalty program—CVS CarePass. Some examples of the loyalty program members’ benefits include:

  • 24-hour access to the helpline
  • 20% discount on specific products
  • Free 1-2 day delivery on qualifying prescriptions
  • Promotional reward worth $10 issued monthly for $5/month or $48/year membership fee

Prioritize the customer experience

Delivering exceptional customer experiences is vital to post-holiday customer retention—around 61% of customers will switch to a competitor after having one bad experience. It’s important to make sure that every interaction with your brand, from website navigation to customer support, is seamless and enjoyable. 

This even involves how you handle some issues that can happen along the way, such as when the payment for the subscription renewal fails to come through. Failed payments can happen due to maxed-out credit cards, insufficient funds, or suspected fraud. A lot of subscription businesses tend to overlook this, but as these failed payments pile up, it can lead to a huge uptick in involuntary churn. 

Here are some concrete actionables you can check out that will contribute to better CX:

  • Conduct usability testing to improve website navigation and checkout processes.
  • Use surveys and feedback mechanisms to gather insights into customer satisfaction and areas for improvement. You can check this list of survey tools to explore.
  • Monitor social media and online reviews to promptly address and resolve any customer complaints or concerns.
  • Set up a hassle-free, enjoyable, and informative onboarding experience for new subscribers
  • Execute a dunning sequence for failed payments and combine it with a failed payment recovery strategy to facilitate a smooth experience for your subscribers


Spotify takes a straightforward approach (but with a sense of urgency) to their payment failure alert email. 

Implement omnichannel customer service options

Omnichannel customer service ensures that customers can reach you through their preferred communication method, whether it’s email, live chat, phone, or social media. Your subscribers want answers, and they want it fast—52% expect to get answers to their inquiries within one hour after posting them on digital channels.

Here are some major things to remember about omnichannel customer service: It’s not simply about being present on all channels. It’s about being present on the channels that matter—the channels where your customers are. Finally, it’s about how you tie in all communications among all those channels. 

Quick checklist for seamless omnichannel customer service:

  • Integrate customer service tools and platforms for consistent communication across channels. There are many help desks and tools that can do this.
  • Monitor and respond to customer inquiries and feedback on all channels promptly.
  • Use data analytics to identify common customer issues and proactively address them.
  • Consider outsourcing your customer service strategy and manpower to experts


The Recover Payments platform helps Failed Payment Recovery Specialists track and monitor the progress of the recovery process across various channels.

Ready to chart the course for long-term success?

The holiday season is not just a time of giving; it’s a time of receiving — a flood of new and excited subscribers.

Remember that the true measure of subscription success lies not in the initial acquisition of these customers but in your ability to nurture these relationships into lasting and loyal subscriptions.

While the holiday retention strategies discussed earlier will definitely help with boosting customer loyalty and retention, it would also be good to ensure that you have all bases covered. This means having a failed payment recovery system in place to make sure that your involuntary churn rate isn’t skyrocketing. 

When it comes down to it, a seamless customer experience is really the answer to subscription businesses’ retention challenges. When you have a solid customer experience strategy across your entire customer journey, customers will be satisfied and loyal.

If you want to discover more tactics to outperform your competition all year around, you need to be at SubSummit 2024 from June 17-19. This is your chance to connect and learn from the largest DTC subscription community