How to Sell Subscriptions Online: 8 Effective Strategies

Over the past decade, the subscription economy has grown by an impressive 435% to a projected market size of $1.5 trillion, signaling its staying power as a dominant business model. ^[1] ERP Today. “The Rise of Subscription Economy: A Win-Win for Consumers and Businesses.” Accessed May 19th, 2025. At its core, selling subscriptions offers significant business advantages, most notably, a predictable stream of recurring payments. Beyond that, when you sell subscriptions, there’s the promise of better cash flow management and stronger customer relationships.
For all its perks, selling subscriptions is not without drawbacks. Chief among them is the high likelihood of payment processing issues. Expired credit cards, declined transactions, or billing system glitches can result in the loss of loyal customers and revenue. Likewise, selling subscriptions can increase the risk of chargebacks, often triggered when customers forget they’ve subscribed or believe they didn’t authorize a renewal. 
In this guide, we’ll walk through eight proven strategies for successfully selling subscriptions online — helping you retain customers, increase revenue, and mitigate common risks.

• Subscription models offer reliable revenue and support long-term growth.
• In subscription business models, customer retention is just as important as acquisition.
• Start small and scale strategically to minimize risk and optimize growth.

Benefits of the Subscription Model

Between 2012 and 2018, subscription-based businesses grew nearly five times faster than S&P 500 company revenues. ^[2] McKinsey & Company. “Creating Consumer—and Business—Value with Subscriptions.” Accessed May 23rd, 2025. This growth shows how stable and scalable these models can be, especially during sales fluctuations. Selling subscriptions has proven to keep customer acquisition costs at a minimum, build a more loyal base, and maintain consistent cash flow.

Types of Subscription Services

With about 75% of Americans subscribing to at least one streaming service, consumers are already familiar with recurring billing. ^[3] The Wrap. “Gen Z Subscribes to 26% More Apps and Streaming Services Than the Average American.” Accessed May 23rd, 2025. You no longer have to sell the concept of the subscription model, just the value of your service or product.

For those interested in starting a subscription business, here are some popular models:

• Subscription Boxes: This includes physical goods delivered on a set schedule, usually weekly or monthly. 
• Membership and Digital Access: Subscribers receive unrestricted access to paywalled content or exclusive digital services.
• Subscribe and Save Model: If you sell on an online marketplace, you might encourage clients to make recurring payments and receive a discount on future product purchases.
• Recurring Donations: By prompting donors to set it and forget it, nonprofits can benefit from the consistency it brings to fundraising. 

8 Strategies to Sell Subscriptions Online

Whether you’re looking to launch a subscription-only business or sell subscriptions within your existing business, these eight strategies will help increase your success.

1. Upsell to Annual Plans

By mitigating churn rates, annual plans outperform monthly subscriptions in terms of lifetime customer value. ^[4] Antenna. “Understanding The Relationship Between Annual Plans And Promotions.” Accessed May 23rd, 2025. Start by offering a generous, exclusive discount to customers who commit for an entire year upfront. However, there’s a caveat. For annual subscriptions, businesses must demonstrate the value and cost savings of making the switch.

2. Offer Flexible Pricing Options

Tiered pricing helps attract a broader audience. For instance, you can offer a basic package with the most fundamental features, a standard package that’s a jump-up from basic, and a premium package that includes superior quality, extra features, or both.

The basic package exists as both a loyal customer and someone who can potentially convert into a higher tier level.

3. Optimize the Product/Service Page

The goal of your service page is to help customers fully understand your value proposition for their commitment to a subscription-based relationship with your business. To that end, focus on clear, succinct descriptions, forgoing bold wording and overpromises.

If there’s any additional value, such as discounts or exclusive content, communicate that to the reader. Additionally, consider displaying testimonials on the product page. As many as 72% of clients trust brands more after reading positive customer reviews. ^[5] Forbes. “How To Increase Brand Trust By Upping Your Social Proof Game.” Accessed May 23rd, 2025.

4. Be Transparent with Billing Details

Clearly communicate price points, payment schedules, renewal policies, and cancellation terms. The more transparent you are about the nuances of your offering, the fewer chances of cancellations and chargebacks.

Subscription businesses are already at risk of these consumers initiating a chargeback to recoup their money for a subscription they forgot about. By being as clear and detailed as possible, merchants can guard themselves against excessive chargebacks while working in a highly chargeback-prone industry. 

5. Identify and Reduce Churn

Customer churn has long been an issue for most subscription businesses. Reducing churn is possible. First, you need to understand the “why” behind canceled subscriptions. Are customers ditching your service because of subpar customer service, lack of perceived value, or something else entirely? Carefully assessing your churn data can help uncover patterns and common pain points.

One often overlooked instigator of churn is payment processing mishaps. Expired credit cards, declined transactions, or billing system hitches can inadvertently boot loyal customers off your platform.

6. Leverage Free Trials

It’s impossible to overstate how much prospective customers appreciate free trials. New data shows 30-day free trials have a customer acquisition rate of 32% and conversion rate of 56%. ^[6] App Developer Magazine. “Free Trials Have High Customer Conversion Rate.” Accessed May 23rd, 2025. Despite their success, nearly 75% of eCommerce sellers didn’t adopt this strategy in 2023, missing a key opportunity for growth.

A free trial encourages customers to experience your services before they commit to a subscription. To them, it’s a safer approach compared to no-trial subscriptions. Use the emails and phone numbers dropped during initial signups to conduct targeted follow-ups to expedite conversions.

7. Partner with Influencers

A modern business model may benefit by leveraging modern marketing tactics, like influencer marketing. For every dollar spent on influencer marketing, businesses stand to earn $5.78. ^[7] Digital Marketing Institute. “20 Surprising Influencer Marketing Statistics.” Accessed May 23rd, 2025. It makes perfect sense: Influencers already have a highly engaged audience that can generate instant buzz around a product or service.

What influencers do better than anyone else is cultivate intimate relationships with their audiences over time. This level of connection gradually translates to credibility and trust that not even the finest ads can match. When an influencer recommends something, it feels more like a friend’s endorsement than a sales pitch.

8. Use Personalized Content Marketing

Content marketing that doesn’t speak to your target audience’s unique needs, pain points, and interests will hardly resonate with them. Even if they give your subscription business a chance, they may unsubscribe down the road because they feel misunderstood, not valued, or both.

You can tip the scales in your favor by customizing your content and communication with simple email headlines. You could, for instance, send targeted emails based on a user’s browsing behavior or offer special discounts on their birthday.

9. Continuous Optimization Based on Data Analysis

Data analysis can help you measure specific details about customer behavior. These metrics include their average purchase amount, how much time they spend on your site, which links brought them to your site, how much they’re engaging with your social media posts, their click-through rate (how often they click on a specific link after seeing it) the percentage of customers who saw your ad or post and clicked, and conversion rate. These insights can help you tailor their experience with your service or product to particularly appeal to them. ^[8]Professional & Executive Development: Harvard Division of Continuing Education. “How to Leverage Marketing Analytics to Improve Customer Relationships and Business Decisions.” Accessed May 23rd, 2025.

How to Retain Subscription Customers

Acquiring a new customer can cost five times more than retaining an existing one. ^[9] Avidly Agency. “What Is the Cost of Attracting New Customers in Comparison to Retaining?” Accessed May 23rd, 2025. Here are some strategies to keep your subscribers loyal, engaged, and subscribed to your offerings.

Building Customer Loyalty

Customer loyalty is the heart and soul of the subscription model, the fabric holding everything in place. To get subscribers to swear by your subscriptions, create a relationship with the customer that goes beyond the usual formalities, deliver consistent value, and make sure your branding is cohesive.

With a well-planned feedback loop, you’ll know firsthand what’s working and what’s not. Reviews and regular surveys are excellent channels for soliciting honest feedback about your subscription offerings. Use all the feedback you’ve garnered to elevate your offering continually and forge stronger connections with your subscribers — your bottom line will thank you for it.

It’s worth mentioning that this tactic is two-fold. It functions as market research among your customers and can also be leveraged as testimonials on your website to drive conversion rates.

Loyalty is a rare and precious thing. Rewarding it shouldn’t be an afterthought. For customers who stay with you long enough — say, six months or a year — show them you appreciate their unwavering commitment by offering thoughtful incentives. That could be anything from cash-back offers to limited-edition products.

Loyalty programs are especially important for businesses offering specials and discounts upfront. They help alleviate the friction of those offerings prioritizing new subscribers over older subscribers. They make all subscribers feel seen, valued, and appreciated.

Enhance the Subscriber Experience Through Payment Processing

More often than not, the greatest contributor to high churn isn’t the emails you didn’t send or the exclusive perks you didn’t offer. It’s the online payment processing option you didn’t consider.

Failed payments make up 20% to 40% of subscription churn. ^[10] DesignRush.  “How To Reduce Churn Rate in Subscription-Based Apps: 8 Proven Strategies.” Accessed May 23rd, 2025. In other words, fixing recurring payment issues within your model can result in up to 40% more revenue. We can help. At PaymentCloud, we offer continuity subscription merchant accounts with features to help you successfully sell subscriptions online.

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