The Customer Success Café Newsletter

The Customer Success Café Newsletter

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The Customer Success Café Newsletter
The Customer Success Café Newsletter
Stop 'Spray and Pray': Use These Triggers Instead
GUIDES

Stop 'Spray and Pray': Use These Triggers Instead

Hakan @ The CS Café Newsletter's avatar
Hakan @ The CS Café Newsletter
Mar 14, 2025
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The Customer Success Café Newsletter
The Customer Success Café Newsletter
Stop 'Spray and Pray': Use These Triggers Instead
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Every SaaS company with a freemium model faces a key challenge:

How do you engage thousands of free users when your CSM team can only focus on paying customers?

The answer is not about sending more emails but sending the right messages at the right moments.

Why Your Free Users Matter More Than You Think

If you're like most SaaS companies, a significant portion of your user base might never speak to a CSM.

Yet these users represent:

  • Your most cost-effective growth channel (when converted)

  • An invaluable source of product feedback and feature validation

  • Potential brand advocates even before they pay

  • A foundation for sustainable revenue growth

The challenge is not to reach these users but rather to engage them in a way that feels personalized without requiring individual attention.

The #1 Mistake in Tech-Touch Programs

Most companies rely on time-based sequences:

Emails sent on days 7, 14, and 30 after signup, regardless of how users are actually engaging with your product.

This "spray and pray" approach damages your brand by treating all users the same.

Behavior-Triggered Engagement: The Proven Alternative

Pipedrive discovered this firsthand.

When they shifted from time-based to behavior-triggered communications, they saw a 27% increase in feature adoption among free users in just 30 days.

Instead of blasting generic newsletters, successful companies map user behavior and automate personalized content at key moments:

  • Activation milestones - When users complete (or struggle with) critical first actions

  • Usage threshold alerts - When they approach 75% of free plan limits

  • Feature discovery opportunities - When usage patterns indicate they'd benefit from specific features

  • Engagement intervention - When activity drops below defined thresholds or shows signs of potential churn

The Success Potential Framework: Where to Start

Even without sophisticated tools, you can begin by mapping users on two key dimensions:

  • Usage depth - How thoroughly they use their adopted features

  • Feature breadth - How many different features they engage with

Users who score high on both metrics have the highest "success potential" and should be prioritized in your conversion efforts.

As one customer success leader discovered:

"We completely transformed our free-to-paid conversion funnel using the behavior-triggered approach described here. We identified our highest-potential users and targeted them with contextual messaging by mapping users on usage depth and feature breadth. This resulted in a 34% lift in conversion rates while reducing our overall email volume by 40%. The ROI was indisputable within the first quarter." — J.D., Chief Customer Officer at a leading B2B SaaS platform

Want To Implement This Approach?

In the premium section below, you'll get:

  • 🔐 The complete Success Potential Formula with detailed 0-5 scoring criteria that identifies your prime conversion candidates (users scoring 16+)

  • 🔐 Four plug-and-play automation workflows with actual message templates for key moments in the user journey

  • 🔐 Comparative data on open and unsubscribe rates across 12 SaaS companies including Intercom, Calendly, and Miro

  • 🔐 Tech stack comparisons to help you select the right tools for your scale

  • 🔐 An exclusive Tech-Touch ROI Calculator to project conversion improvements and calculate revenue lift

Don't miss these actionable insights that could transform your free-to-paid conversion rates!

🔐Premium Section: The Tech-Touch Conversion Blueprint—Advanced Strategies

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