Chase unpaid invoices without feeling awkward

Let an agent do the reminding on a schedule, so you never have to feel awkward about it.

Most unpaid invoices aren't disputes. They're forgotten. A short, regular reminder fixes most of them, and an agent can write those reminders so you don't have to dread doing it.

Start with a list

Export unpaid invoices from your billing tool (Stripe, QuickBooks, Xero all do this) with the customer, amount, due date and any failed-payment reason. Give the agent that list and nothing else. It should never guess who owes what.

A simple schedule

• 3 days overdue: friendly note with the invoice link. Assume it slipped through.
• 14 days: a second note with the amount and due date stated plainly, and an offer to help if the card failed.
• 30 days: a clear, polite message about what happens next (service paused on a stated date).

Rules for the agent

1. Draft only. You read and send every reminder.
2. Use the exact amount and invoice number from the export. No rounding, no "around".
3. If the payment failed, say why in plain words ("your card was declined") and how to update it.
4. Check the thread first. If they already replied or paid, no reminder.
5. Never threaten, never guilt-trip. Short and factual reads as professional.

Run it weekly

Once a week, ask: "Using this unpaid list, draft the reminder each customer is due for, and skip anyone who replied or paid since." Five minutes of reading and sending replaces a task most solo founders put off for months.

• More guides
• Find buyers on Reddit without spamming →
• Schedule a morning run that works while you sleep →
• Turn every customer into a project file AI can read →