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The fourth email is the one that gets paid

You already know how to invoice. What breaks is the follow-up: two polite nudges, a week of hoping, and then the invoice quietly becomes a story you tell at dinner.

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The actual problem

Chasing an invoice is not a workflow problem. It is an embarrassment problem wearing a workflow problem's clothes.

The first reminder is easy — it can be framed as helpful, a copy in case the original got buried. The second is fine. By the third you are aware that you are the person who keeps emailing about money, and by the fourth most people simply stop, tell themselves the client is going through something, and absorb the loss. The invoice does not get written off in the accounts. It gets written off in the head, which is worse, because it never shows up anywhere you could count it.

Every tool in this category sells automation as a time saving. That framing is wrong for anyone billing under a hundred invoices a month; the time cost of sending five emails is fifteen minutes. What automation actually removes is the decision to send each one. A schedule you set once, when you are not annoyed and not embarrassed, sends the message you would have sent if you had been braver.

The default ladder

Fixed, visible, and editable before it starts. Days are counted from the due date, not the send date.

Day −3
Heads-up
Before it is late. A single line confirming the amount and the date, which resolves a surprising share of invoices that were only ever going to be late because nobody diarised them.
Day +1
First reminder
Neutral, short, with the invoice attached again. No apology and no explanation of why you are writing.
Day +7
Second reminder
Names a person. Asks a question that has an answer — is this waiting on approval, or on a payment run?
Day +14
Escalation
Copies the finance address if there is one, states the late fee if your terms have one, and asks for a payment date rather than payment.
Day +30
Final notice
States what happens next in plain language: work paused, statutory interest applied, or the account passed on. Whatever you actually intend to do, and nothing you do not.

Source: Default schedule; every step is editable and any step can be removed before the ladder starts.

Why the tail matters

reminders most freelancers send before giving up: 2
messages in the default ladder: 5
expected launch price, per month, unlimited invoices: $19

Against the tools you would otherwise use

The honest summary: if you are happy inside FreshBooks or Zoho, use their reminders and keep your $19.

Question	Late Invoice Nudges	FreshBooks	Chaser	Nothing
Works on invoices raised elsewhere	Yes	No	Via your accounting system	Yes
Entry price	$19/mo expected	from $21/mo	from about £50/mo	$0
Requires changing how you invoice	No	Yes	Yes	No
Messages after the second reminder	Three more, scheduled	Configurable	Configurable	Rarely sent
Who it was designed for	One person	One person	A finance team	Nobody

Competitor prices are their published entry tiers as of August 2026 and change often. Check before you decide anything.

What it would cost

Published before it exists, on purpose. A price is the only question that costs you something to answer.

Expected launch price

$19per month

Founder price$9 per month

This product does not exist yet. The number above is the price we expect to launch at, not a commitment. If the waitlist says it is wrong, it changes.

What the price covers

Unlimited invoices and unlimited clients
The five-step ladder, editable, per client if you want
Sends from your own address, so replies come back to you
Stops automatically on payment, reply, or a word from you
Export of everything, any time, no export fee

What it does not cover

Invoicing. It does not create invoices and is not trying to.
Debt collection, legal escalation, or anything involving a credit bureau
Payment processing

The founder price is held for as long as the account stays open, which is the only promise worth making before a product exists.

The three objections that are actually good

My invoicing tool already does this.: Then use it. That is the correct answer for most people reading this, and it is why the comparison above puts FreshBooks and Zoho in the same table rather than in a strawman. This exists for the person invoicing from a spreadsheet, a PDF, or a payment link, who is not going to migrate an entire billing history to get a reminder.
Automated chasing will damage the relationship.: It can, if the messages read as automated. The ladder above is deliberately five short human sentences rather than a branded dunning template with a red header. But the real answer is that the relationship is already being damaged — by you going quiet, then resentful, then odd on the next project.
I would rather just call them.: Calling works better than email and almost nobody does it. If you are a caller, you do not need this. The ladder exists for people who will not pick up the phone, which is most of us, and a message that goes out is worth more than a call that does not.

Would you pay $19 a month for this?

The tier you pick is the whole signal. Nothing else on this page matters as much.

The rest of this cluster

Asking for payment
The wording matters less than the sequence. Here is the sequence, and then the wording.
Late fee calculator
Run your own numbers first. Most people are surprised, and not in the direction they expected.
Email templates
Short, unbranded, and free of the two phrases that make a reminder easy to ignore.
Chaser alternative
Written by someone who thinks Chaser is good. That is not the problem with it.
Days sales outstanding
A real metric, borrowed from a context that does not resemble yours.
Pix Reconciliation
Brazil's instant payment scheme settles in seconds and tells you almost nothing about why. That gap is a monthly afternoon for a great many small businesses.