Chase unpaid PayPal invoices with escalating reminders

Every weekday at 9am in my workspace timezone, chase my unpaid PayPal invoices for me, and make the chase get firmer the longer an invoice has been outstanding. Use a cron trigger running Monday through Friday at 9am.

Start with PayPal Search Invoices to pull every invoice that is still unpaid and already past its due date. Filter on the unpaid and partially paid statuses and on a due date earlier than today, and page through the whole result set rather than stopping at the first page, so a long receivables list is never silently truncated. Ignore drafts and cancelled invoices. For each invoice, capture the invoice id, the invoice number, the recipient name, the recipient email address, the original total, the amount still due, the currency and the due date. If a search result is missing any of those fields, call PayPal Get Invoice on that invoice id to fill in the detail before deciding what to do with it.

Before acting on anything, apply two filters. First, skip any invoice whose outstanding balance is below a nuisance threshold I can configure at the top of the workflow, defaulting to 25 in the invoice currency, since those are not worth spending goodwill on. Second, never chase the same invoice more than once every seven days. Keep a running chase log that persists between runs, recording the invoice id, the date it was last contacted and which bracket it was in, and skip any invoice contacted within the last seven days. As a second check before sending a personal email, use Gmail List Messages to search my sent mail for that invoice number over the last seven days, and skip the invoice if a follow up already went out.

For every invoice that survives those filters, work out how many days past due it is and put it in one of three brackets. Handle each bracket differently.

Bracket one, 1 to 14 days overdue: send a single polite nudge with PayPal Send Invoice Reminder. Keep the accompanying subject and note warm and factual, assume the invoice was simply missed, and do nothing else for this invoice.

Bracket two, 15 to 44 days overdue: send the PayPal Send Invoice Reminder as above, and then also write and send a firmer, personally worded follow up with Gmail Send a Message to the billing contact on the invoice. Write that email fresh for the specific invoice rather than filling in a template. It must name the invoice number, the exact amount still outstanding, the original due date and how many days it has now been overdue, and it must ask for either payment or a clear date by which they will pay. The tone should be noticeably more direct than the first bracket while staying professional and never threatening. If the invoice has no recipient email address, skip the Gmail step for that invoice and note it for the Slack summary so someone can fill the address in rather than guessing at one.

Bracket three, 45 or more days overdue: do not auto send anything. Send no PayPal reminder and no email. Instead, draft a final notice in my voice and post the invoice to Slack with Send a Message to my finance channel so a human decides what happens. The Slack post should name the customer, the invoice number, the amount outstanding, the due date and the days overdue, include the full drafted final notice text so it can be copied, edited or discarded, and spell out the three choices in front of us: hand the account to collections, offer a payment plan, or write it off. Make it obvious that nothing has been sent to this customer yet and that the decision is theirs.

Update the chase log for every invoice you actually contact or post about, so the seven day rule holds on the next run. Finish with one short summary message to the same Slack channel covering how many invoices were nudged, how many got a personal follow up, how many are waiting for a human decision, the total value outstanding across everything reviewed, and any invoices skipped for a missing email address or for falling under the threshold.