A free guide by Arina Tannenbaum ↗ Instagram ↗ Facebook
Turn last month's customers
into next week's revenue
Your next sale probably is not a stranger. It is someone who already paid you once and quietly drifted off. Here is the exact 20-minute play to write a five-message win-back sequence with Claude and put it in front of every past customer this week. You build it once, and you can run the same play every month. On May 13, 2026 Anthropic launched Claude for Small Business, so the tool you need for this is now aimed squarely at owners like you.
01
Pull your past customers
The money is in the list you already have. You do not need a fancy CRM. Your booking tool, point of sale, or email inbox already knows who paid you and when. You just need three things per person: their name, what they bought, and roughly when they last came in. Fifteen names is enough to start seeing replies.
Open your booking tool, POS, or email and list everyone who bought in the last 90 days. Put name, what they bought, and last visit date into a simple note. Stop at the first 15 to 25 people so you actually finish today.
02
Hand Claude the brief
Claude does not need a clever prompt. It needs context. Tell it who you are, what you sell, the one offer you want to make, and the tone you talk to customers in. Ask for five short messages spaced across a week, each under 40 words, each with one clear next step. Short wins, because these go out as texts and quick emails, not newsletters.
Paste this into Claude: "You are writing for my [type of business] in [city]. My past customers bought [service] and have not been back in a while. Write a five-message win-back sequence to send over one week. Each message under 40 words, warm and human, no hype. Make one clear offer: [your offer]. End each with one simple next step."
03
Send it and track replies
A sequence in a document makes zero dollars. Sending it is where the revenue shows up. Personalize the first line of message one with their name and what they bought, then send in small batches so you can reply fast when people answer. Watch for replies, not opens. A reply is a customer raising their hand.
Send message one to your first 15 people today by text or email. Drop the other four into your calendar across the next week. When someone replies, answer within the hour and book them in. That speed is the whole game.