You got to the checkout a while back.

Someone signs up, picks a plan, reaches your checkout, and leaves. Maybe the price was wrong that day, maybe they got pulled into a meeting. They are the closest you have to a customer, and almost nobody writes to them. This finds them in Stripe and writes each one a short note from one person on the team, about what changed since they looked.

What it does

• Finds everyone whose checkout expired without a payment, and who has not paid since.
• Writes in rounds of about a hundred, newest checkouts first, so the freshest interest goes first.
• Holds back 1 in 5, always the same people, so you can see whether the notes work.
• Two days after a round goes out, counts who paid, against the people held back, and who replied. Again at a week. Writes it all down.
• Changes exactly one thing in the next round (the subject, the first line, an answer to the question people kept asking), and says what and why.
• Never writes to the same person twice, and never to someone held back.
• Leaves every note in the sender’s Gmail Drafts until you turn on auto-send.

The reveal

Round one goes to 92 people who left your $199 checkout in the last month, telling them about the new $49 plan. Two days later: 6 paid, and 1 of the 18 held back did. Three replies asked whether the $49 plan has the same skills. Round two answers that in its first line.

Configuration

• Who to write to: everyone whose checkout expired unpaid. Narrow it in chat (“only the $199 plan”, “only since September”).
• Who sends the notes: one person on the team, from their own account.
• The note: what changed since they looked (a new plan, a feature, a price), in the team’s words, and the link back.
• Rounds: about a hundred people, at least 48 hours apart.
• Held back: 1 in 5.
• Auto-send: off until the sender turns it on in chat.
• How often: when you ask, or every 2 hours if an available scheduler can run the work and you approve it. A new round waits 48 hours after the last one went out.

What it doesn’t do

• It doesn’t send until you turn on auto-send.
• It doesn’t invent a discount. It only says what the team told it changed.
• It doesn’t write to anyone twice, anyone who paid, or your own team.
• It doesn’t change two things at once, so each round’s result says which change worked.

Triggers

Runs when you ask (“follow up with the people who left checkout”, “how did the last round do”). Scheduled checks need a verified scheduler and your approval; otherwise it writes one round now and saves where it got to.