Subscription Prescription | Weekly Doses to Boost Ecommerce Revenue

Most email agencies spread out your subscriber onboarding emails to avoid "over-sending." I think that's backwards. In this episode, I break down the email and SMS strategy that actually drives retention for subscription brands.

What we cover:
• Why you should send more emails in the first few days, not fewer
• The onboarding window most brands completely waste
• How to turn your billing reminder into a retention tool
• Why SMS reduces churn instead of causing it
• The campaign paradox: skipping billing reminders but blasting daily promos
• Building subscriber-specific offers and campaign strategies

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Jade Moffett from Dirtea joins the show to break down how they use education-first onboarding, segmented winback flows, and direct mail to retain and re-engage subscribers. We dig into why they wait to cross-sell, how their CX team shapes retention messaging, and the 200% lift they saw from Paper Run.

What we cover:

• Why education-first onboarding drives long-term retention
• Segmenting winback flows by cancellation reason and product
• Using direct mail (Paper Run) to re-engage churned and opted-out customers
• Cross-sell timing: why waiting until after the first subscription cycle matters
• How feedback loops at every touchpoint improve the customer experience
• Balancing short-term revenue with long-term customer value
• Letting your CX team sense-check retention messaging

Guest: Jade Moffett
Her LinkedIn: https://www.linkedin.com/in/jade-moffatt-42ba35199/
Website: https://www.dirtea.com

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In this episode, I break down the three psychological triggers that keep subscribers from hitting the cancel button, and how you can use them to reduce churn.

What we cover:

• How reducing friction and anxiety prevents cancellation impulses
• Why identity reinforcement makes subscribers feel like they belong
• The role of habit formation in building long-term commitment
• Practical ways to apply these triggers in your subscription business

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Free trials are everywhere in DTC, but most brands struggle with what matters most: turning trials into full-price buyers and subscribers. In this episode of Subscription Prescription, I’m joined by Jose Vigo, founder of Healthy Metal, a magnesium sleep brand built around sachets and a “try it first” acquisition strategy.

We unpack how a shipping-only trial can work, what drives conversion after the sample arrives, and the practical systems that bring customers back. We cover:
How Healthy Metal uses a shipping-only trial to acquire new customers
What actually influences trial-to-full conversion (product experience, price, and expectations)
The post-trial follow-up stack: inserts, email flows, retargeting, and flash offers
Testing direct mail with Paperrun, including a “personal letter” vs discount mailer experiment
Offer page experimentation in Replo, choice reduction, and AOV tradeoffs with multi-box subscriptions
Why sometimes breaking “best practices” is exactly what makes a model work
Connect with Jose here: https://www.linkedin.com/in/josevigocasais/

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If I only had a couple of days to improve a subscription program, this is exactly where I would start.

In this episode of Subscription Prescription, I walk through a mini subscription workshop focused on fast, high-impact fixes. These are practical changes you can make quickly to increase subscription opt-in, reduce churn, and improve retention without rebuilding your entire stack. We cover:
Why defaulting to subscribe and save matters and how small design changes drive uptake
How to upsell subscriptions in the cart when customers choose one-time purchase
Turning billing reminder emails into value reminders instead of charge notices
What to fix first inside your cancellation flow to improve save rates
When aggressive discounts actually make sense for retention
How a simple splash screen or founder video can reduce cancellations
Building an onboarding sequence that reinforces value and sets expectations
Longer-term offer tests like bulk subscriptions, starter kits, and gifts
This episode is built for operators who want results quickly and need a clear order of operations for improving subscriptions. New episodes of Subscription Prescription drop every Tuesday. Subscribe to stay notified.

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