Late payments aren't always about reluctance to pay. Often, invoices get buried in inboxes, marked for later, and forgotten. A well-timed reminder solves this without awkwardness.
When to Send Reminders
Before Due Date (2-3 days)
A gentle heads-up: "Your invoice is due in 3 days." This catches people who intended to pay but forgot. Keep the tone helpful, not demanding.
On Due Date
A simple reminder: "Your invoice is due today." No guilt, just information. Include a direct payment link.
After Due Date (3-7 days)
Now it's overdue. The tone shifts slightly: "Your invoice was due on [date]." Still professional, but clearer about the expectation.
Escalation (14+ days)
For significantly overdue invoices, more direct communication may be needed. Consider a phone call or personalized email at this stage.
What Makes a Good Reminder?
Be Brief
Reminders should be short. The customer knows they owe you money—they just need a nudge and a way to pay.
Include the Payment Link
Every reminder should include a direct link to pay. Don't make them search for the original invoice.
Stay Professional
Never guilt, shame, or threaten (except in extreme situations handled by lawyers, not automated emails). Professionalism preserves the relationship.
Provide Context
Include invoice number, amount, and what it's for. Customers shouldn't have to dig to understand the reminder.
Automating Reminders in Stripe
Stripe's built-in reminders are limited. For more control, you need either:
- Custom development using Stripe's API and webhooks
- A billing platform that adds reminder functionality
Conto Billing includes automated reminders that work with your Stripe invoices—configure them once and let them run.
How Many Reminders Is Too Many?
There's no universal answer, but a reasonable sequence might be:
- 1 reminder before due date
- 1 reminder on due date
- 2-3 reminders after due date (spaced increasingly apart)
After 4-5 reminders over 3-4 weeks, you're likely dealing with a different kind of problem that requires personal attention.
The ROI of Reminders
Most overdue invoices aren't intentional. They're forgetfulness, busy schedules, or email overload. Reminders recover a significant portion of these payments without any difficult conversations.
The time you save not manually following up, plus the payments you recover, easily justifies the effort of setting up automation.