Unpaid invoices persist not because chasing is hard but because it is unpleasant, so humans defer it. That makes it close to the perfect first automation: frequent, rule-shaped, emotionally taxing, and measured in money. The steps above are the whole build; the notes below are what experience adds.
| 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 |
The truth-source step is where projects die. If your ledger says unpaid and your spreadsheet says paid, the automation inherits the argument. An afternoon reconciling state beats a month of apologising.
Tone is a specification, not a vibe. Write the three escalation messages yourself once, in your own words, and let the system vary details rather than voice. The agent job description template is the right container, and a fortnight of approval-only drafts proves the voice on real arrears before anything sends.
Guardrails are the professional finish: stop on reply, stop on part-payment, per-client caps, exclusions for the accounts where a call beats a letter, and logging that ties every send to the invoice for the day someone asks. The chasing pattern generalises to documents and signatures with the same skeleton.
Where I fit in
This playbook is a standard Kick-starter shape: scoped and priced in writing, built on the tools you already pay for where possible, shipped with the drafts-first trial period and the measurement included. If it is the process your team sighs about, bring it to a call and you will leave with the honest version of effort, cost and payback.