Automate invoices and payment follow-up

What it is

Late payments hurt cash flow, and manual chasing takes time. Automated invoicing sends the invoice when work is delivered or a subscription renews, follows up on unpaid invoices on a schedule, and escalates to a person when reminders don’t work.

How it works

1. Create invoices or subscriptions in your payment platform.
2. Turn on the built-in reminders first. Stripe can email automatic reminders for unpaid one-off and recurring invoices, scheduled before, on or after the due date, and skips a reminder when a payment is already processing. It can also retry failed subscription and invoice payments automatically with Smart Retries.
3. Add custom automation only where you need it. Stripe sends webhook events when invoices are finalized, paid or marked uncollectible. Use them to trigger your own steps, such as an AI-drafted personal note for a long-overdue account or a task in your CRM.
4. Escalate to a person after a set number of reminders. Stripe can mark an invoice uncollectible once it is 30, 60 or 90 days past due, or leave it past due.

Benefits

• Faster payment, less chasing.
• A consistent, professional tone.
• A clear record of every reminder.

Limits and risks

• Keep money movements with a person. Stripe’s MCP server requires human confirmation before certain write actions, such as refunds and outbound payments. Apply the same rule to any automation you build.
• Reminder tone affects relationships. Review the wording of escalating reminders before they go out.
• Tax and accounting rules are out of scope here.