Dose #191: From Trial to Subscription: What Works (And What Doesn't)

Matt here with your weekly Subscription Prescription 💊

I’ve seen a lot of free trial offers, or free (when you pay shipping) offers in my day. They struggle to work, for a variety of reasons. In this week’s dose, however, we dive into what makes them work and what you can do to improve how people are first testing your products.

This week’s dose is also a full podcast interview with Jose Vigo, the founder of Healthy Metal. We talk through his free + shipping trial program, and more about his subscription program. Take a watch or listen on your favorite program:

Let the Paper Run

Paper Run has reimagined direct mail specifically for subscription brands. It helps brands like Grüns, Neuro, Create, Ancestral, Heights, Spacegoods, and many more identify, reach, and convert customers who aren’t opening their emails by sending them physical mail.

In a world where email and SMS are can no longer be relied on to reach every customer, subscription brands are turning to Paper Run en masse to pick up the slack.

With native integrations in Recharge, SKIO, Stay AI, and Loop, Paper Run helps brands build automated, measurable direct mail flows that print and deliver every day - ensuring brands can always get the right message to the right people at the right time.

How subscription brands are using Paper Run:

• Win back cancelled subscribers who can’t otherwise be reached
  

• Increase second-order rates for one-time purchase (OTP) customers with replenishment reminders
  

• Retarget abandoned carts, checkouts, and site visitors who can’t otherwise be reached

Paper Run is making direct mail one of the easiest wins for subscription brands in 2026. For a limited time, Subscription Prescription readers receive 20% off Paper Run. Just let them know how you heard about them to receive the discount!

Free + Shipping Offers

Free plus shipping offers are one of the most polarizing tactics in subscriptions. Some operators swear by them. Others say they attract low-quality customers who never convert.

The truth is neither extreme is fully right. Free trials are not inherently good or bad. They are simply a different acquisition engine. If you treat them like a discounted product launch, they will disappoint you. If you treat them like the first step in a habit-building system, they can work remarkably well.

Here are three lessons I keep coming back to when evaluating a free-with-shipping strategy.

1. The trial must create a habit, not just a sample

Most brands think the goal of a trial is to get the product into someone’s hands. That is only partially true. The real goal is to create belief and integration into a routine.

If your product works quickly, you might get a night-one moment. Sleep, hydration, or energy supplements sometimes create that immediate association. But even then, one positive experience is not the same as a formed habit.

If your product takes longer to show results, a one-day trial will not cut it. The customer needs enough time to use it multiple times, experiment with timing, and start associating it with a routine. The longer they integrate it into their behavior, the more natural it becomes to reorder.

The mistake most brands make is thinking “cheap entry” equals “easy conversion.” It does not. Conversion happens when someone feels, “This is now part of my routine.”

Takeaway:

• Design your trial length around habit formation, not cost minimization.

• Reinforce how and when to use the product immediately after it arrives.

• Measure how usage behavior correlates with trial-to-full conversion.

2. The product and pricing jump must make psychological sense

One of the biggest friction points in free-plus-shipping offers is the transition from a low-cost trial to a full-priced box.

If someone pays a small shipping fee and then sees a large full-box price, that gap can feel disproportionate, even if the math makes sense. This is especially true in wellness categories where the perceived benefit is subjective.

Sometimes the fastest way to improve trial-to-full conversion is not another email. It is aligning price expectations. That could mean testing a lower first-box price, offering a strong welcome discount, or structuring the offer so the first paid order feels like a continuation rather than a leap.

It is easy to focus on ad creative and funnels. But often the unlock is simpler: the perceived value-to-price ratio at the moment of the first paid commitment.

Takeaway:

• Audit the psychological gap between trial price and first full purchase.

• Test price reductions or clearer value framing before adding more complexity.

• Remember that conversion friction is often about perceived fairness, not just product satisfaction.

3. Follow-up is where the real conversion work happens

If you stop at email flows and retargeting ads, you are underutilizing the opportunity created by a trial.

A trial customer has raised their hand. They have shared an address. They have shown intent. That is a higher-quality signal than most cold traffic.

This is why layered follow-up matters. Inserts inside the trial package that guide next steps. QR codes that make reordering simple. Educational emails that reinforce usage. Retargeting audiences built specifically from trial users. Even physical mailers that show up a few days after the product lands.

The goal is not to spam them. The goal is to stay present while the product is being experienced. The more touchpoints that reinforce your story, mission, and benefits during that window, the more likely conversion becomes.

Takeaway:

• Treat trial customers as a high-intent audience with a dedicated conversion stack.

• Combine packaging inserts, email, paid retargeting, and optional direct mail.

• Use a proper holdout group when testing so you know what is actually working.

Bottom line

Free plus shipping is not a shortcut. It is a front-end lever that shifts your acquisition model. If you run it without a habit strategy, without pricing alignment, and without a serious post-trial conversion plan, it will disappoint you.

But if you build the system behind it, it can become one of the most powerful ways to introduce customers to your subscription.

Until next Tuesday, that’s your Subscription Prescription. 💊

 - Matt Holman 🩺

The Subscription Doc