How to Nurture Engaged Readers into Higher Subscription Tiers

Pete Ericson, CEO & FounderZEEN101

We’ve all been there. You’re paying for a service, enjoying the content, and then BAM! You hit a wall. Suddenly, the thing you thought you had access to is locked away, and the service is demanding more money. It’s a frustrating experience that leaves a bad taste in your mouth.

Why a Bad User Experience Kills Loyalty

Take the recent experience of one sports fan. He was a paying subscriber to a major sports network, happily watching the early rounds of a major tennis tournament. But when the quarterfinals came, the stream wouldn’t load. After 20 minutes of confusion, he discovered his plan didn’t include the later rounds of the very tournament he had already started. To keep watching, he had to pay more.

The experience was jarring:

  • His expectations as a paying customer were shattered.
  • There was no communication or “nurturing” to let him know an upgrade was needed for the full tournament.
  • The upgrade process was a confusing mess of more than a dozen different options.

This is a masterclass in what not to do. When you frustrate your customers, you lose their trust and their business. The sports fan upgraded to watch the finals, but what did he do right after? He downgraded. You don’t want your subscribers to feel hassled; you want to build a relationship that lasts.

A Clear Path for Your Readers

You can grow paid subscribers without being pushy. The secret isn’t a complex web of plans and premium tiers. It’s about creating a simple, clear, and predictable path for your readers to follow. Think of it as a nurturing on-ramp that guides a casual visitor into becoming a loyal, paying supporter.

By setting clear expectations and making your subscription model easy to understand, you reduce churn and build a more stable revenue stream.

The key is a simple funnel that sets clear expectations, nurtures with value, and uses low-friction upgrade paths. When done right, you move readers from free to paid and from monthly to annual with higher trust and less churn. 

Building Your Nurturing On-Ramp

Don’t try to reinvent the wheel. Simplicity wins. For most publishers, this means starting with two core options: a monthly plan and an annual plan.

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Here’s what the ideal nurturing path looks like, step by step:

  • Free Registration: Start by offering something for free in exchange for an email address. This gets readers on your newsletter list and gives them access to a couple more articles, letting them sample your value before committing.
  • Monthly Subscription: This is the perfect entry point for new subscribers. It’s a lower-commitment way for them to try you out and get full access to your content.
  • Annual Subscription: Your goal should be to encourage monthly subscribers to upgrade to an annual plan. They save a little money, and you lock in a loyal reader who is far less likely to churn. Mark it as your “Most Popular” option, because it should be.
  • The “Third Card”: Once a reader is on an annual plan, they’ve signaled they’re in for the long haul. This is your chance to offer more ways for them to support you. Your “third card” on the pricing page could be one of several options:
    • Donations: Ask your most loyal readers to contribute more to support your mission.
    • Gift Subscriptions: This is a hugely underrated revenue source. Experts from the print world say that gift subscriptions can account for up to 20% of your paid subscribers.
    • Group/Corporate Subscriptions: Offer plans for businesses, schools, or other organizations. Direct them to a separate page with a form to discuss their specific needs.

Creative Ways to Encourage Upgrades

Sometimes, all you have to do is ask. One publisher sent a simple email campaign to their subscribers. They explained how they were investing in more reporters and better coverage and asked if readers would consider upgrading from a $10/month plan to a $20/month “super supporter” plan.

The magic was in the execution. To upgrade, all subscribers had to do was reply “Yes” to the email. No forms, no buttons, no hassle. The result? Over 100 people said yes within a few days, adding over $1,000 in new monthly recurring revenue. Some even asked to donate extra on top of the upgrade.

Key takeaways

  • Simplify Your Offerings: Avoid overwhelming readers with too many choices. A simple monthly and annual plan is often all you need, as these are what customers have come to expect.
  • Meet Customer Expectations: A paying customer expects to get access to the content they signed up for. Suddenly requiring an upgrade mid-event, like ESPN did, creates a frustrating and negative experience.
  • Build a Nurturing Path: Guide your readers on a journey. Start with a free registration to capture an email, then offer a monthly plan, and encourage them to move to a more stable annual plan.
  • Offer More for Loyal Supporters: For your most committed readers, provide options beyond a standard subscription, such as donations, corporate/group plans, or gift subscriptions, which can be a significant source of revenue.
  • Use Friction Strategically: For nonprofits, one way to encourage donations is to offer free content but require users to renew their free access every 24 hours. Paying to remove this friction becomes a powerful incentive.
  • Make Upgrading Effortless: To encourage existing subscribers to move to a higher-priced plan, send a direct email explaining why the extra funds are needed and ask for a simple “Yes” in reply to upgrade them. This removes all hassle for the user.

Your pricing strategy is more than just numbers on a page; it’s a journey you guide your readers


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