How to follow up with free trial users (and turn more into paying customers)

Most trial follow-up is a calendar: day 1 welcome, day 3 tips, day 12 "your trial is ending". It's easy to set up and easy to ignore, because it treats the person who never logged in the same as the person who used your product every day.

The better signal is what they did. A trial user is in one of a few places:

• Signed up, never set up. They hit a snag or lost interest. Ask one question: what were you hoping to do?
• Set up, but no key action yet. Point them to the one feature that makes the product click.
• Active, not paying. They like it. Ask what would make it worth paying for, or offer a short call.
• Hit a limit or opened the pricing page. This is the moment to talk about the plan that fits.
• Paid. Stop sending trial emails at once. Nothing annoys a new customer more.

Write each note like a person: short, about their situation, from a real mailbox, with one question. One good note at the right moment beats five on a schedule.

How AO does it: connect PostHog read-only, and AO turns your product events into meanings: signed up, finished setup, used a key feature, invited a teammate, wants more. New sign-ups become leads. In Settings › Pipeline you choose which event moves a person to which stage, so your trial users sort themselves.

Then start a broadcast from an offer, such as "a 14-day pilot for sign-ups who haven't paid". Pick the audience by stage: you see the count, a preview, and who's left out and why. AO writes each email for one person. The first one waits for your approval and sends from your own Gmail or Outlook. Paying customers are never included, and anyone who books a call stops getting the broadcast. Every email carries your company's name, postal address and an unsubscribe link.