#60: Struggling to get free trial users to upgrade? Do this

#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

Join the SaaS Marketing Weekly Newsletter here: https://saasmarketingweekly.com/

Check out Ryan’s agency, Rocket SaaS, here: https://rocket-saas.io/

Send podcast guest pitches to: info@rocket-saas.io

Episoder(92)

#92: How to reach your ICP without burning your entire budget

#92: How to reach your ICP without burning your entire budget

In this episode, Ryan dives deep into where your audience actually hangs out and how to tap into those hidden goldmines. From podcast appearances and newsletters to Slack communities and industry even...

28 Apr 17min

#91: The sub-brand strategy behind Rocket SaaS hitting $5M ARR

#91: The sub-brand strategy behind Rocket SaaS hitting $5M ARR

In this episode, Ryan deep dives into one of the game-changing strategies that helped Rocket SaaS scale to $5M ARR, creating an educational sub-brand. He walks through the steps of building a separate...

21 Apr 19min

#90: Webinar recording: 10 SaaS marketing campaigns that actually work

#90: Webinar recording: 10 SaaS marketing campaigns that actually work

In this episode, Ryan shares a full masterclass breaking down 10 different ways to get SaaS customers. Not all growth tactics are created equal, and most companies are wasting time on the wrong ones. ...

14 Apr 53min

#89: Rocket SaaS hits $5,000,000 ARR. How we did it

#89: Rocket SaaS hits $5,000,000 ARR. How we did it

In this solo episode, Ryan shares the full story behind Rocket SaaS hitting $5M ARR — and why the journey was far from smooth. From years of slow, frustrating growth to a handful of key decisions that...

7 Apr 25min

#88: Webinar recording: The LinkedIn Ads playbook for scaling SMEs

#88: Webinar recording: The LinkedIn Ads playbook for scaling SMEs

In this webinar recording, Ryan and Jamie break down the real LinkedIn Ads playbook behind scaling B2B SaaS companies and SMEs. They share what’s actually working right now, what most teams get wrong,...

31 Mar 1h 7min

#87: Startup? What qualities should you look for in a marketer?

#87: Startup? What qualities should you look for in a marketer?

In this episode, Ryan and Jamie break down what founders should look for when hiring their first marketing person. Many startups make the mistake of hiring a specialist too early, only to realise they...

24 Mar 19min

#86: 6 ways to get revenue, when you need it FAST

#86: 6 ways to get revenue, when you need it FAST

In this episode, Ryan and Jamie share six powerful campaigns you can run right now to bring in fast revenue, even if your sales cycle is usually long. From digging into your closed lost deals to using...

17 Mar 26min

#85: How to reach everyone with one piece of content

#85: How to reach everyone with one piece of content

In this episode, Ryan shares the secret to maximising content reach by repurposing one piece of content across multiple formats. From podcasts and webinars to short-form videos, blogs, and LinkedIn po...

10 Mar 7min

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