How many emails should I send during a 14-day free trial?

Six to eight emails is the sweet spot for 14-day trials. Fewer than six and you're leaving conversions on the table. More than eight and you risk annoying engaged users. Adjust based on trial length—7-day trials need 4-5 emails, 30-day trials can support 10-12.

Should trial emails come from marketing or customer success?

Customer success. These are onboarding emails, not promotional campaigns. Users expect help, not sales pitches. If your CS team is small, have the founder or a product manager send them—authenticity matters more than perfect email design.

What's the best time to send free trial emails?

For B2B SaaS, send between 10 AM and 2 PM in the user's timezone on Tuesday through Thursday. For B2C products, evenings (6-8 PM) and weekends often perform better. A/B test your audience specifically—behavior varies by industry.

Can I use the same sequence for 7-day and 14-day trials?

No. Compress the 14-day sequence by cutting the Day 6-7 email and moving the objection handler to Day 5. The core framework stays the same, but timing accelerates.

How do I handle users who sign up but never log in?

Send one simplified activation email 24 hours after signup with a single action button. If they still don't log in after 3 days, send a final "Is this still a priority?" email offering to pause their trial or schedule a quick call. Don't keep emailing beyond that.