60 • Struggling to get free trial users to upgrade? Do this

In this episode, Ryan dives into one of the most important levers for SaaS growth: your onboarding experience. Too many companies get plenty of free trial signups but fail to convert them into paying customers. Ryan explains what industry benchmarks look like, why onboarding often fails, and how to design an experience that drives users to activation. From signup flow and guided tours to gamification, personalisation, and email onboarding, this episode is packed with practical ways to increase your conversion rate and reduce churn.

Takeaways:

• Average free trial → paid conversion = 15–25%; below 15% means something is broken
• Define your activation milestone (e.g. Slack = 2,000 messages; Dropbox = 10 files saved) and build onboarding around it
• Keep signup flows short — name, email, password; use Single Sign-On to reduce friction
• Use guided tours, tooltips, and short videos to highlight only key actions (not every feature)
• Personalise onboarding for different roles or use cases
• Add quick wins & gamification (progress bars, rewards, incentives) to keep users engaged
• Provide educational resources, but make them optional and easy to find
• Add a human touch — personal messages or LinkedIn DMs can increase upgrades
• Use email onboarding flows (5–8 emails over 30 days) to re-engage inactive trial users
• Leverage product data to spot drop-off points and re-engage before churn happens

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By Ryan James

Founder of Rocket SaaS