Invoices stay unpaid because chasing is unpleasant rather than hard, so people put it off. That makes it close to the ideal first automation: frequent, rule-based, draining to do, and measured in money. The steps above are the whole build, and the notes below cover what tends to go wrong.
| The build at a glance | |
|---|---|
| Best first candidate when | Arrears exist and chasing is dreaded |
| Human gate | Every send, until tone is proven |
| Stops automatically on | Payment, part-payment, any reply |
| Measured by | Days sales outstanding; chases-to-payment |
| Typical shape | Fixed-price Kick-starter |
Getting the invoice status right
The source of invoice status is where these projects most often fail. If your ledger says unpaid and your spreadsheet says paid, the automation inherits the disagreement and chases a client who has already paid. An afternoon sorting that out is better than a month of apologies.
Writing the tone down
Write the three reminder messages yourself, once, in your own words, and let the system change the details rather than the voice. The agent job description template is a good place to record them, and a fortnight of approval-only drafts tests the voice on real arrears before anything goes out on its own.
The guardrails
Stop on reply, stop on part-payment, cap the chases per client, exclude the accounts where a phone call works better than a letter, and log every send against its invoice for the day someone asks. The same chasing pattern works for client documents and signatures.