What it does
Checks trial users’ activity and triggers SMS reminders to log in or book support if they’ve been inactive ahead of expiration.
Why I recommend it
Human outreach right before trials expire dramatically improves conversion.
Expected benefits
- Higher trial-to-paid conversion
- Insight into friction points
- Better CS coordination
- Lower no-decision churn
How it works
Daily check -> find trials expiring in 3 days with last login >5 days -> Twilio SMS with CTA to training/resources -> optionally notify CSM to follow up.
Quick start
Send manual texts to a subset and compare conversion vs control.
Level-up version
Personalize by use case, include quick links to book onboarding calls, and escalate to phone call if user ignores text.
Tools you can use
Product analytics: Mixpanel, Amplitude
Messaging: Twilio, Attentive
CRM: HubSpot, Gainsight
Automation: Zapier, Customer.io
Also works with
Webinar attendance reminders, SaaS trial nurture emails.
Technical implementation solution
- No-code: Analytics export -> Zapier -> Twilio SMS + CSM task.
- API-based: Data warehouse -> AI -> multi-channel outreach via Customer.io.
Where it gets tricky
Ensuring SMS opt-in, time zone compliance, and not spamming engaged users.
