You sent an invoice two weeks ago. Crickets.
Now you're staring at a blank email, trying to word a follow-up that sounds professional but not desperate. "Just circling back..." Delete. "Wanted to touch base..." Delete. "Following up on..." Ugh.
Meanwhile, that unpaid invoice is sitting in someone's inbox, buried under 200 unread messages.
There's a better way. Three simple automations that handle the awkward stuff for you—reminders, payment links, escalations—while you focus on actual work.
The Problem with Manual Invoice Follow-Ups
Most small business owners waste 3-5 hours per month chasing payments:
- Tracking which invoices are overdue (spreadsheet gymnastics)
- Drafting follow-up emails (writer's block every time)
- Second-guessing the tone ("too pushy?" "too soft?")
- Forgetting to follow up until it's really overdue
And here's the worst part: the delay costs you money. The longer an invoice goes unpaid, the less likely you are to collect. After 90 days, recovery rates drop to 70%.
The 3-Automation System
Here's what you're going to build:
- Automation #1: Friendly reminder 3 days before due date
- Automation #2: Payment link reminder on due date
- Automation #3: Escalation sequence for overdue invoices (7, 14, 30 days)
💡 Real Result
A marketing agency using this system cut their average payment time from 38 days to 18 days. That's $12K in cash flow freed up per month.
Tools You'll Need
This setup uses tools you might already have:
- Invoicing software - QuickBooks, FreshBooks, Wave, or Stripe Invoicing (all have APIs)
- Zapier or Make.com - To connect everything (free tier works)
- Email - Your existing email (Gmail, Outlook, etc.)
Total cost: $0-29/month depending on your invoicing software. Most scenarios: free.
Automation #1: The Friendly Heads-Up (3 Days Before Due)
This isn't a nag—it's a helpful reminder. Catches invoices before they're late.
How to Set It Up:
- In Zapier/Make, create a trigger: "Invoice due date approaches" (most invoicing tools support this)
- Add a filter: "3 days before due date"
- Send an email with this template:
Subject: Quick heads up: Invoice #[NUMBER] due [DATE]
Body:
Hi [Name],
Just a friendly reminder that Invoice #[NUMBER] for [Amount] is due on [Date].
Payment link: [LINK]
Let me know if you have any questions!
Why this works: It's proactive, not reactive. You're being helpful, not chasing. And that payment link? One-click convenience = faster payment.
Automation #2: Payment Link on Due Date
The invoice is due today. Send another reminder—with extra friction removed.
Setup:
- Trigger: "Invoice due date = today" AND "status = unpaid"
- Email template:
Subject: Invoice #[NUMBER] due today - Pay in 2 clicks
Body:
Hi [Name],
Invoice #[NUMBER] for [Amount] is due today.
[BIG BUTTON: Pay Now]
Takes 30 seconds. No login required.
Pro tip: Make the payment button LARGE and obvious. Visual prominence = action.
Automation #3: The Escalation Sequence (For Overdue Invoices)
This is where you save hours. Instead of manually tracking overdue invoices, the system handles it:
- Day 7 overdue: Polite reminder
- Day 14 overdue: More direct tone + late fee notice (if applicable)
- Day 30 overdue: Final notice before escalation
Setup:
Create 3 separate Zaps/scenarios, each with a time delay:
Day 7 Email:
Subject: Following up: Invoice #[NUMBER] is 7 days overdue
Body:
Hi [Name],
I wanted to check in—Invoice #[NUMBER] is now 7 days overdue.
Is there anything blocking payment? I'm happy to help resolve any issues.
[Pay Now Button]
Day 14 Email:
Subject: Action required: Invoice #[NUMBER] is 14 days overdue
Body:
Hi [Name],
Invoice #[NUMBER] is now 14 days past due. Please process payment by [DATE] to avoid late fees.
Amount due: [AMOUNT] (+[LATE FEE if applicable])
[Pay Now Button]
Day 30 Email:
Subject: Final notice: Invoice #[NUMBER] - Action required
Body:
Hi [Name],
Invoice #[NUMBER] is 30 days overdue. This is a final notice before we escalate to collections.
Please contact me immediately if there's an issue. Otherwise, payment is required within 5 business days.
What This Saves You
Let's do the math:
- Average time per manual follow-up: 15 minutes (find invoice, draft email, send)
- Invoices sent per month: 20
- Follow-ups per invoice (average): 2
- Total monthly savings: 10 hours
That's a full workday back. Every month. Forever.
Plus: You get paid faster. The average business cuts payment time by 40-50% with automated reminders.
Bonus Tips
- Add payment terms to invoices: "Net 15" or "Due upon receipt" removes ambiguity
- Use payment links, not bank transfers: Stripe, PayPal, Square—make it one-click easy
- Track open rates: If someone isn't opening emails, call them. The automation tells you when to intervene
- Personalize the sender: Send from your actual email (you@company.com), not an invoicing tool. Feels more human
Common Objections
"Won't this annoy my clients?"
Nope. Clients expect reminders. What annoys them is surprise late fees or passive-aggressive emails. Automated reminders are predictable and professional.
"What if I have different payment terms for different clients?"
Tag clients in your invoicing software (e.g., "Net-30" vs "Net-15"). Set up different automation paths for each tag.
"My invoicing software doesn't integrate with Zapier."
Most do (QuickBooks, FreshBooks, Wave, Stripe, Xero, Zoho). If yours doesn't, consider switching—this one automation alone justifies it.
Next Steps
Start with Automation #1 (the 3-day reminder). It's the easiest and has the biggest impact.
Once that's running, add #2 and #3. The whole system takes 15-30 minutes to set up, depending on your invoicing tool.
Then? Sit back and watch your average payment time drop. And those awkward "just following up" emails? You'll never send one again.