HOW TO REACTIVATE YOUR DORMANT USERS

➤ WELCOME TO ISSUE #2

I’m happy your back! If you’re like me, you spent the better part of last week analyzing how the economy and current events are affecting your recurring revenue.

Here’s the thing, every dormant user represents revenue you've already paid to acquire, and reactivating that dormant user costs 5-7x less than acquiring new ones

Let that sink in, then continue reading. Here’s what we’ll cover:

• The 5-step win-back sequence that top subscription apps use to recover churned revenue without spending additional ad dollars

• How to segment dormant users effectively, matching messages to specific user behaviors

• The Context-Agitate-Promise framework that makes win-back messages 3x more effective than generic "we miss you" emails

• Why progressive incentives outperform standard discount tactics in reactivation campaigns

➤ THINGS YOU SHOULD KNOW

• FTC Enforcement on Auto-Renewing Subscriptions: The FTC’s new “Click to Cancel” Rule takes effect May 14, 2025, requiring clear disclosures, easy cancellations, and explicit consent for all auto-renewing subscriptions.

• Thomson Reuters Reports First-Quarter 2025 Results: Thomson Reuters reported 9% growth in recurring revenues for Q1 2025, outpacing transactional revenue growth and highlighting the strength of subscription models in professional services.

• Shopify Subscription Optimization: The global subscription e-commerce market is forecast to grow from $326.44 billion in 2024 to $539.16 billion in 2025 (a 65.2% CAGR).

➤ TODAYS FOCUS

💰 Most subscription businesses focus obsessively on acquisition while neglecting the gold mine in their churned user database.

The managers who redesign their operations around systematic win-back processes see immediate revenue impact without spending additional ad dollars.

This isn't about sending random "We miss you" emails.

This is about engineering a precision-targeted win-back machine that delivers predictable results.

⚡ The 5-Step Win-Back System

Step 1: Segment Your Dormant Users by Behavioral Signals

Dormant users are not a monolith; they churned for different reasons. That’s why it’s important to create distinct segments:

• Usage depth before churn (power users vs. barely touched)

• Time since last active session (recent vs. ancient)

• Feature adoption (which core features did they use)

• Subscription tier and total lifetime value

Each segment requires a different win-back approach.

High-value past subscribers who used your product extensively need different messaging than those who barely got past onboarding.

Set up your dashboards to automatically move users into these segments based on behavior.

Step 2: Design Your Cadence Architecture

Build a precise contact schedule by segment.

• Power users who recently churned: 3-day, 7-day, 14-day, 30-day, 60-day touch points.

• Low-engagement churns: Day 1, Day 5, Day 15, Day 30.

Structure the entire flow before writing a single message.

Map communication channels for each touch:

• In-app if they still have the app installed (assuming your product has an app)

• Push notification (with deep links to re-engagement screens)

• Email (primary channel for most segments)

• SMS (highest urgency, limited frequency)

Document the full sequence in a matrix showing each segment, timing, channel, and core message.

Remember that the system matters more than individual messages.

Step 3: Create Context-Agitate-Promise Messages

Every win-back message must follow the C-A-P framework:

• Context: Remind them specifically how they used your product. "You tracked 27 workouts with us last quarter."

• Agitate: Surface the problem they're experiencing without your product. "Your fitness data is now scattered across multiple platforms."

• Promise: Offer a clear, immediate value proposition. "One tap restores your full fitness dashboard with all historical data."

Notice: no "we miss you" generics. The message needs to speak directly to their specific use case and problem.

Each segment receives customized C-A-P messaging based on its historical behavior.

👉 I created some C-A-P examples to help you out. You can view them here.

Step 4: Implement Progressive Incentives

Structure incentives that escalate through the sequence. Start with no discount, just value reminders.

Then progress to time-limited offers of increasing value:

• 7-day extended trial

• 25% off the first month

• 50% off for three months

• Special returning-user annual plan

Two crucial elements:

1. Each offer expires before the next one appears

2. Later, higher-value offers require more commitment

Document your incentive ladder in a sequence matrix. Test different incentive structures against a control group to validate ROI.

Step 5: Build Closed-Loop Measurement Systems

Implement attribution tracking for every reactivation. My advice, create dashboards showing:

• Win-back rate by segment

• Revenue recaptured per sequence

• Conversion by message and channel

• ROI of discount offers

Establish a weekly win-back review process with stakeholders, and continuously optimize based on data:

• Test message variants against control groups

• Compare channel effectiveness

• Adjust timing based on open/click patterns

Success metrics:

• Reactivation rate above 5%

• 3-month retention of reactivated users

• Positive ROI on all discount offers

🤓 Optimization Points for Maximum Impact

The best win-back systems include these refinements:

• Behavioral triggers: Restart sequences when dormant users show interest (app open, website visit).

• Progressive personalization: Increase message specificity with each touch.

• Multi-person approval chains: Design sequences for B2B apps where multiple stakeholders influence reactivation.

• Time zone optimization: Schedule delivery when users are historically engaged.

The win-back sequence isn't just a retention tactic. It's an operational discipline that innovative product leaders institutionalize.

👉 Need a specific example of what a win-back message sequence might look like? I put one together for you here!

➤ TILL NEXT WEEK

That’s a wrap…

Remember: Revenue operators who build systematic, measurable win-back operations recover 10-20% of churned revenue without spending additional acquisition dollars.

Start by implementing just one segment with one sequence. Measure the results. Then expand.

And so it’s clear: The best time to build your win-back system was when your first customer churned. The second best time is today :)

Hope this was useful!

Cheers,

~ Rick

P.S. Will you do me a favor? Please reply to this email with feedback, comments, or questions; I read all of it.

P.P.S. You can use the poll below to let me know what you thought of this newsletter issue. Your feedback is greatly appreciated, thank you!