How do I use AI to follow up with customers who haven't bought from me in a while?
Use AI tools like Mailchimp's AI content tools, Klaviyo's AI-powered segments, or simply Claude or ChatGPT to draft a 2–3 email win-back sequence targeting customers inactive for 90+ days. Pair the drafted emails with your email marketing platform's automation triggers so the follow-up sequence fires automatically when a customer hasn't purchased within your defined window.
The first step is knowing which customers have gone quiet. If you're on Shopify, WooCommerce, or Square, you can export a list of customers and their last purchase dates with a few clicks — or use the built-in lapsed customer segment if your platform offers one. Klaviyo (klaviyo.com) is particularly powerful here: it can automatically build a segment of customers who bought between 91 and 180 days ago and haven't returned, and then trigger an email sequence to that segment without you touching it again. For Mailchimp (mailchimp.com) users, set up a tag-based automation with a date-based trigger. Once you have your segment, bring the customer data to Claude (claude.ai) or ChatGPT. Paste in: your business type, the product category they bought, how long they've been inactive, and any offer you're willing to make. Ask for a 3-email win-back sequence with subject lines and body copy. A well-prompted AI will produce all three emails in under 3 minutes — something that might have taken a copywriter a full afternoon. The offer matters more than the copy. Studies consistently show that a win-back email with a discount or incentive converts at 2–3x the rate of a plain "we miss you" message. For service businesses, a free consultation, free estimate, or complimentary add-on often outperforms a percentage discount. Ask the AI to draft versions with and without an offer so you can test both. Once you've got your emails, load them into your email platform as a triggered automation. The whole setup — identifying the segment, drafting the emails, and loading them — can be done in about two hours the first time. After that, it runs on its own indefinitely. Even a 5% win-back rate on lapsed customers can represent a meaningful revenue lift, especially for businesses with high average order values.