The first reminder is easy. It goes out a day or two after the due date, it’s gentle, and it’s practically apologetic. Just checking this didn’t get lost. Anybody can write that one, and nearly every business sends it.
The fourth is where sequences die.
By then the invoice is five or six weeks overdue, three messages have been ignored, and whoever is writing has to make a choice they’d rather not: get firm and risk the relationship, or stay soft and accept that this message will be ignored like the last three. Faced with that, most people do neither. They stop writing.
Chasing Co. writes the fourth reminder. This is about how.
We read a lot of other people’s mail first
Before writing a line of Chasing Co.’s messaging we spent weeks reading follow-ups that experienced credit controllers actually send. Not templates. Real threads, shared with permission, from people whose ledgers were in good shape.
What stood out wasn’t toughness. It was specificity, and an evenness of tone that barely changed between the first message and the fourth.
The good ones never apologised for asking. They also never threatened. Every message carried the invoice number, the amount, the original due date and the simplest possible next step. Every message assumed good faith. I expect this is an oversight turned up far more often than any version of you have failed to pay. And every one left a door open: a question, an offer to resend the PDF, a direct phone number.
The escalation lived in the structure, not the adjectives. First message, a nudge. Second, plainly stating it’s overdue. Third, noting it’s now been a month and asking for a date. Fourth, saying that without a date the account goes to the business owner. Which isn’t a threat, because it’s simply what happens next.
The rules
We turned that into a small set of rules and hard-coded them. Chasing Co. can vary its tone within a sequence, warmer for a fifteen-year customer, more formal for a large corporate, but it can’t break these.
Be specific. Invoice number, amount in the invoice currency, original due date, days overdue. Never “your outstanding balance.” The customer shouldn’t have to look anything up to know what’s being asked of them.
Don’t apologise, don’t threaten. Chasing Co. won’t write “sorry to bother you.” It also won’t write “failure to remit will result in.” It writes like a competent, busy person who expects to be paid and assumes you intend to pay.
Stop the moment they reply. Any reply halts the sequence. Even “who is this?” Chasing Co. reads it, works out what it is, and either answers, reschedules or hands over. It never fires the next scheduled reminder into a live conversation, which is the single most common way automated chasing makes a customer angry.
Never chase a dispute. If a reply reads as a complaint, short delivery, wrong price, work not signed off, “we never got this”, the invoice is paused and the whole thread goes to the account owner. Chasing Co. doesn’t argue. It doesn’t know the facts of your job and shouldn’t pretend it does.
Escalate to a person, not a penalty. The fourth message says the account owner will be in touch, because that’s true. Chasing Co. never mentions lawyers, collection agencies or credit reporting. Not on any plan, not ever.
Follow the customer to their channel. Email first, always. SMS if they haven’t opened email across two touches, or have replied by SMS before. WhatsApp only where they’ve used it with you already or asked for it. Chasing Co. doesn’t cold-message anyone’s personal number.
What it actually says
Here’s a real one, names changed. Sent by email forty-one days after the due date, to a customer who had opened but not replied to three earlier messages.
Hi Meredith — following up again on invoice 2291 for A$18,400.00, which was due on 3 July and is now 41 days overdue. I’ve not had a reply to my earlier notes, so I want to be straightforward: if I can’t get a payment date from you by Friday, I’ll pass this across to Daniel, who owns the account, to pick up with you directly. If there’s a problem with the invoice, tell me and I’ll pause everything while we sort it out. Otherwise, the easiest way to settle is BPAY — biller code and reference are on the attached. Thanks, and I hope to hear from you.
Look at what it’s doing. It names everything. It says, without heat, that the earlier messages went unanswered. It sets a deadline with a consequence, and the consequence is a person rather than a penalty. It leaves a clean exit if there’s a genuine problem. It ends with the easiest route to paying.
Meredith replied inside an hour with a remittance date. Most people do. The fourth reminder works not because it’s clever but because it exists, and because it’s recognisably the same calm voice as the first three.
Why software should write it
There’s a fair objection here. Surely the fourth reminder is precisely the one a human should write, since it carries the most judgement.
I’d argue the opposite. The judgement, when to escalate, what tone fits which customer, what happens to a dispute, gets made once, by you, at setup. The hard part isn’t deciding what to say. It’s saying it on day forty-one to the twelfth customer that week without softening it because you’re tired or skipping it because you’re slammed.
That’s not judgement. That’s consistency, and consistency is one of the few things software genuinely does better than people.
Chasing Co. makes the fourth reminder as reliable as the first. Whatever conversation follows is yours.