Here's a number most trades owners don't want to think about: the average small contractor has 15–20% of invoices go past 30 days. On $40,000 a month in revenue, that's $6,000–$8,000 sitting in someone else's bank account because nobody followed up.

The work is done. The invoice is sent. The money just never came.

An AI agent doesn't feel awkward about following up. It doesn't forget. And it doesn't let anything slip.

The Invoice Follow-Up Sequence

This automation runs every morning and handles your entire outstanding invoice queue. Set the rules once — it runs forever.

// Copy-paste prompt (abbreviated)
Every morning at 8am, check my invoices for outstanding balances. Apply this sequence: Day 7: "Hi [name], just a friendly reminder that invoice #[number] for $[amount] is due. Let me know if you have any questions — [Your name]" Day 14: "Hi [name], following up on invoice #[number] for $[amount] — still showing as outstanding. Happy to set up a payment plan if that's helpful. — [Your name]" Day 21: "Hi [name], invoice #[number] for $[amount] is now 21 days past due. Please reply to arrange payment or call me directly at [phone]. — [Your name]" Day 30: Flag for my personal review. Add to "collections" list. Stop automated outreach. Rules: Never contact the same customer more than once per week. Never send to customers with an open dispute. Put all messages in drafts — do not send automatically.

Automation 2: New Invoice Confirmation

Cash flow problems often start before an invoice goes overdue. This automation confirms every invoice the moment it's sent — dramatically reducing "I never got the invoice" excuses.

// Copy-paste prompt (abbreviated)
When I send a new invoice, immediately send the customer a text: "Hi [name], invoice #[number] for $[amount] just hit your inbox from [Business Name]. Payment is due [date]. Reply with any questions — [Your name]"

Automation 3: Paid Invoice Thank-You + Review Request

The moment a payment comes in is your best opportunity to ask for a review. This fires automatically when an invoice is marked paid.

// Copy-paste prompt (abbreviated)
When an invoice is marked paid, wait 24 hours, then send: "Hi [name], just saw your payment come through — thank you! If you have 60 seconds, a Google review means everything to a small business: [review link]. Thanks again — [Your name]" Only trigger for residential customers. Skip commercial accounts. Never send if the customer had a complaint on this job.

What This Looks Like in Practice

A plumbing shop in Ohio set up this sequence on a Monday. By Friday they had collected $3,800 in outstanding payments they'd basically written off. That's what happens when you consistently follow up with every overdue invoice, at the right intervals, without fail.

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Frequently Asked Questions

Will automated invoice reminders upset my customers?

Not if the messages are written naturally and respectfully — which the prompts in the guide are. Most customers simply forgot or got busy. A friendly reminder at day 7 is welcome, not offensive. The sequence escalates gradually, and you always have the option to pause it for specific customers.

Can I approve messages before they go out?

Yes — the prompt above specifies "put all messages in drafts, do not send automatically." You review and approve before anything goes to a customer. This is the recommended setup for invoice follow-up specifically.

What about commercial customers?

Commercial accounts often have different payment terms and internal approval processes. The guide covers how to set up separate rules for commercial vs. residential, including longer grace periods and different escalation paths.