I need a streamlined automation that pulls purchase data from my Square account, checks when each customer is likely to run out of a specific product, and then sends a timely SMS reminder that also suggests related items they might enjoy. The trigger dates vary by product—some need a nudge after 60 days, others after 125—so the workflow has to let me set custom rules per SKU rather than a fixed weekly or monthly cycle. My first thought is Zapier, but I’m open to any tool (Make, Pabbly, a direct API build, etc.) that can watch Square transactions, calculate the next-buy window, and fire the text through an SMS provider such as Twilio or Plivo. AI-style logic to fine-tune timing or personalise copy is welcome as long as the system stays easy for me to adjust. What matters most is: • Connection to Square that reliably captures new sales in real time • Flexible scheduling based on product-specific intervals I define • SMS content that covers “time to reorder” plus a short product recommendation pulled from my catalogue • A clear hand-over with documentation so I can tweak copy, dates, and numbers without coding If you have done similar replenishment or win-back automations, show me an outline of how you’d wire this together and which services you’d lean on. Once we agree, I’ll provide sample SKUs and message copy so you can build, test, and roll it out live.