An unpaid invoice has two causes. They need opposite messages.

Most shops open the overdue list once a month and send everyone the same “just following up” email. That is a payment demand to people who never got a bill, and “did you get this?” to people who read it twice.

Two reasons, not one

It never arrived. Spam, a typo in the address, an office manager who left, or a commercial job where it went to the site contact instead of accounts payable. The client is not avoiding you. They do not know there is a bill.

It arrived and they read it. They are short this month, waiting to be paid themselves, unhappy with a line item they never mentioned, or they forgot. Resending the same PDF fixes none of it.

Guess wrong and it costs you. Press someone who never got the bill and you have accused a good customer of ducking you. Ask “did this reach you?” of someone who read it and you have said something they know is false.

What Jobber actually records

Status tells you the clock is running, nothing more.

Past Due means a date went by, not why. Jobber surfaces the why better for quotes: a first view triggers a push notification³ and an activity feed entry.² For invoices the feed covers created, sent and deleted only.²

The data exists anyway. The invoice object in Jobber’s API carries a field described in the schema as the date the invoice was viewed in client hub.⁵ Jobber records the view, it just does not show it on the invoice list.⁶

The two messages

Both carry the payment link. A reminder without one is a reminder to go and find it.

No price pressure, no mention of lateness. The only question is whether the bill reached them.

Never tell the client you can see they opened it. It is your own data, and saying it out loud reads as surveillance. Let it decide what you write, not appear in it.

The second message is not apologetic, deliberately. “Sorry to bother you” tells the reader the request is negotiable, and negotiable requests go to the bottom of the pile.

A cadence, not a law

Anyone who says there is one correct schedule is selling something. It depends on ticket size and on whether you are up against an accounts payable cycle. A reasonable default:

1. A few days after the due date. Not so fast that you are chasing a cheque in the post.
2. A week to ten days later. Firmer. Name the amount, ask for a date.
3. Around the month mark. The last one that belongs in an inbox.

Jobber automates part of it. Invoice follow-ups go by email or text to clients who received the invoice and have them enabled. There are two, each set as days after the due date, up to 90. They send shortly after 8AM local time, by the method the invoice went out.⁴

That is a floor, not a strategy. An automation cannot know whether the invoice was opened.

When to pick up the phone

Call after the second written contact gets no answer, and immediately when the amount is big enough to hurt or you suspect a dispute.

Email creates a record and resolves very little. Someone who ignores three emails will give you the real reason in ninety seconds on the phone: a PO name that does not match, a line item they thought was included.

Then write it down. Voice to solve it, writing for the record.

Late fees, and what to put in writing

Check two things before you charge a late fee.

It has to have existed before the invoice went late: in the signed agreement or estimate, or in the invoice terms. A fee that first appears in a chasing email is not a term of the deal, it is a new demand.

What you can charge and enforce is governed by state law and differs by state. This is not legal advice. If late fees are a real part of how you bill, have a lawyer in your state read your terms.

Before it becomes a collections question, put the facts in one message: invoice number, date issued, work performed, amount outstanding, due date, and the dates you made contact. No argument, no threat, just the record.

When to stop emailing

Stop when the third contact goes unanswered. A fourth version of the same email does not raise the odds of being paid, and it turns a recoverable relationship into a blocked address.

After that: escalate to a decision maker by phone, hand it to collections or small claims, or write it off. Bad Debt closes an uncollectible balance out of the client’s billing history.¹ That is not defeat, it clears a dead number out of your receivables.

Silence after three properly sent contacts is itself an answer.

Where we come into it

We build software that splits an overdue list by whether the invoice was opened, and drafts the right one of those two messages in your own voice. It reads your Jobber account; it cannot change anything.

You do not need us for this. It is your own data and both messages are above. What we sell is not the insight, it is not doing it by hand every month. If you want to see what is unpaid and unopened right now, we will read it once, free.