How to chase overdue invoices without sounding like a collections desk

Solo operators rewrite “just checking in” because there is no AR department. Software can make the next action obvious. It cannot change who holds the power on the job. Do not buy a product whose only pitch is AI that writes chase email. People complain about chasing; they do not pay for a tone generator.

A boring schedule that works

Send the invoice before the work is a distant memory. Shorter terms get paid faster in published invoice data; “Net 30” is an invitation to wait 30 days. Due on receipt or Net 7/14 is clearer for project work.

• Day after due: short note. Invoice number, amount, original due date, how to pay, link or PDF. No apology novel.
• Day 3: same facts, ask if they need it sent to AP or a PO added. Wrong inbox is a common stall.
• Day 7: same facts, plus when you will pause further work if that is a lever you actually have. Do not threaten if you will not follow through.

Copy the number, amount, dates, and pay instructions from the invoice. Do not rewrite the bill in the email — attach or link the same document.

What “I never received it” means

Treat it as a resend, not a debate. Word attachments are a black box. A share link you can paste again is more honest than arguing about spam. Email open tracking is noisy. justIssued does not log share-page opens today; the link still beats a buried PDF.

What justIssued will and will not do

Free: outstanding board, overdue on sent invoices past due, statuses, share link. You still send the chase yourself.

Paid: email the invoice from justIssued, and overdue reminders (send now, or optional auto on days 1, 3, and 7 after due when the daily job runs). Auto-remind only fires if you turn the business toggle on. There is no hosted cron in the box — production needs a scheduled hit, or you click Run.

justIssued does not take cards, add late fees automatically, or pretend to be a collections agency. Card checkout is a different product; justIssued does not do Pay now. Mark paid when Interac or the wire lands. Related: invoicing as a freelancer in Canada.