How to Automate Payment Reminders
Get paid on time without the awkward chase
The problem
Invoice is 14 days overdue. You know you should follow up but it feels awkward. You wait another week. Still unpaid. Cash flow suffers. The longer you wait, the harder it is to collect.
The DIY approach
Enable Xero's or MYOB's built-in payment reminders
Set reminders at 7, 14, and 30 days overdue
Manually call or email for seriously overdue invoices
Update your records when payment is received
Where DIY falls short
Built-in reminders are generic and impersonal
No escalation beyond email — no SMS or phone task creation
Reminder sequences can't be customised per client relationship
No visibility into which clients are chronically late
The SmoothSailor approach
Friendly first reminder at 3 days overdue — personal tone, easy payment link
Firmer reminder at 7 days — include invoice summary and payment options
Escalation at 14 days — SMS reminder plus internal task for a personal call
Final notice at 30 days — formal email with late payment terms
Chronic late-payer flagging — identify clients who always pay late and adjust terms
Estimated time saved
2-4 hours/week on payment chasing
Related services
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