How to Automate Invoicing
Get paid faster with automated invoicing and payment reminders
The problem
Invoicing happens at the end of the month — if you remember. By then you've forgotten billable hours, and clients take another 30 days to pay. Manual payment chasing is awkward and time-consuming.
The DIY approach
Set up recurring invoices in Xero or MYOB for retainer clients
Use Xero's built-in payment reminders (7, 14, 21 days overdue)
Manually create project invoices when work is complete
Export time logs to calculate billable amounts
Where DIY falls short
Project invoices still require manual creation and calculation
No connection between PM tool completion and invoice generation
Payment reminders are generic — no escalation to SMS or phone
Time tracking and invoicing are disconnected systems
The SmoothSailor approach
Auto-generate invoices in Xero when projects hit 'Complete' in your PM tool
Time-to-invoice pipeline — logged hours automatically become draft invoices
Escalating payment reminders — email, then SMS, then task for personal follow-up
Payment confirmation notifications posted to Slack for real-time cash flow visibility
Monthly accounts receivable summary auto-generated and emailed to you
Estimated time saved
4-6 hours/week on invoicing and payment chasing
Related services
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