Call · 15 min
AI systemsMattia Esposito2 September 20267 min read

Payment reminders. The first message goes out before the due date.

May's invoice still hasn't been paid, and nobody noticed until there wasn't enough cash to pay a supplier. Then came the awkward phone call, made too late and handled badly. This piece keeps track of due dates and sends messages when they're needed, checking first who has already paid.

In brief

The first message comes before the due date. It doesn't ask for money: it mentions the invoice number, date and amount, and asks the customer to confirm everything is in order. That's when any dispute comes to light, while there's still time.

Customers who've paid get nothing. Before every send, the system checks against the payments recorded, and anyone who's up to date drops out of the sequence automatically.

You decide when to get firmer. The first steps are purely informative; late payment interest, fixed compensation and formal demands are never sent automatically.

This page covers a single piece of the system. The other pieces, and how we choose which one to start with, are on the services page.

What changes in practice

Money comes in sooner because someone is always on top of it, even in the weeks when the business has other things on its plate. Due dates no longer depend on the memory of the person who handles the admin, and the first reminder goes out even on the day that person is on holiday.

The second change is the tone. A message sent three days before the due date is a courtesy to the customer; the same message sent sixty days later is a demand for payment. When the early steps work, the hard ones become rare.

A reminder costs least before it's even a reminder.

In Italy, paying late is the statistical norm, and it's worth knowing that

43.4% of Italian businesses pay on time, and 4.1% run up serious delays of more than ninety days. The figures come from the twenty-second edition of the Cribis Payment Study, based on more than 2 billion payment records across 37 countries.

The European comparison shows how much this is about the system rather than a few bad payers: in Denmark 94.9% of businesses pay on time, in Poland 86.6%, in the Netherlands 74.7%. Italy has slipped to twenty-first place in Europe.

The practical consequence is clear. Treating every late payment as bad faith means writing messages that offend half your customers, who are simply following their usual habits, so the sequence has to be designed on the understanding that here, paying late is normal.

What the law gives you, and almost nobody claims

The right exists, and it doesn't require a formal demand. Article 6 of Directive 2011/7/EU, transposed into Italian law by Legislative Decree 231/2002, puts it like this: “the creditor is entitled to obtain from the debtor, as a minimum, a fixed sum of EUR 40”.

On the same basis, late payment interest accrues from the day after the due date, at the reference rate plus at least eight percentage points. The default payment term between businesses is 30 calendar days, which can be extended to 60 only by express agreement.

The system works out these amounts and shows them next to each account, so when you decide to claim them you know exactly how much is at stake. It never adds them to a document on its own, because asking a long-standing customer for interest is a commercial decision, not a calculation.

What the system does, step by step

Every invoice enters the sequence on its issue date and leaves when it shows as paid, and every step leaves a log entry recording the outcome.

StepWhat happensWhat you get
Calendarfrom your invoices

Due dates are taken from the invoices issued, using the payment terms agreed with each customer.

No due date depends on someone's memory or a reminder on their phone any more.

Checkbefore every send

Before sending anything, the system checks the account against payments recorded and any open disputes.

Customers who've paid don't get chased, and nobody has to apologise for a message sent by mistake.

Reminderbefore the due date

An informative message goes out with the invoice number, amount and date, asking the customer to confirm everything is in order.

Disputes surface while there's still time, instead of turning up as an excuse once the due date has passed.

Sequencetone escalates gradually

After the due date, the steps follow one another at agreed intervals, with the tone changing at each stage.

The customer gets a consistent sequence, not three identical messages followed by silence.

Handoverto a person

Beyond the agreed threshold, the account leaves the automatic process and goes to the person who makes the decisions, with its full history.

You make the difficult call with all the figures in front of you, at the right moment, not six months later.

The payment check, which is what makes the rest safe

Nearly every tool of this kind sends messages on a fixed schedule. That works as long as the schedule matches reality, and it almost never does: a bank transfer that landed yesterday, a deposit entered by hand, a credit note, a dispute someone took over the phone.

Here, before every send, the actual state of the account is checked. If it shows as paid, it drops out; if there's an open dispute, it drops out and goes back to a person; if it's been part-paid, the message changes and refers to the balance. The rule is deliberately lopsided: if in doubt, the system doesn't send.

That's because the two possible mistakes don't cost the same. A missed reminder costs a few extra days of waiting; a reminder sent to a customer who had already paid costs the trust of a customer who did nothing wrong, and sometimes the customer.

This check only works if the records are reliable, which is why this piece is built on the adaptive CRM and automatic document entry: without payments and documents in order, the check has nothing to go on.

What goes out on its own, and what waits for a person

The first two steps, the informative ones, go out on their own, and only on accounts with no open dispute. They're messages that repeat facts already on the invoice, and you keep the switch to turn them on or off, customer by customer.

Nothing that commits the business or changes the relationship ever goes out on its own: late payment interest, the €40 fixed compensation, payment plans, suspending supplies, formal demands. Those are decisions, and they stay with the person who makes them.

Where a message goes out automatically, it says in one line that it comes from a system. From 2 August 2026, Article 50 of the AI Act applies, and how we say it is on the AI transparency page. The reasoning behind keeping a person in the loop is on our page about the principles we build by.

Same mechanism, different name in every trade

The sequence is the same everywhere; the payment that slips through isn't. It's worth looking at your own case, because that's where you see how much money is sitting out there.

SectorThe payment that slips through todayWhere you see it
Food and agricultureand export

A foreign distributor's balance on sixty or ninety days, with different terms for every country and nobody keeping track.

What a first export order costs

Hospitalityaccommodation and events

Deposits due thirty days after confirmation, and the balance after the event, when everyone's attention has already moved on to the next date.

The run-up to the season for a guest accommodation business

Restaurantsand bars

Invoices to companies for business lunches and group dinners, which are few and far between, and that's exactly why nobody chases them.

A dinner service with the phone ringing unanswered

What this piece doesn't do

It isn't a debt collection agency, and it doesn't send formal demands. It prepares, reminds, calculates and hands the account to a person; legal action and out-of-court recovery are a different profession, and stay with the people who practise it.

It doesn't tell you who to sell to or set a customer's credit limit. It shows how they've paid in the past, which is useful to know before accepting a large order, and the decision stays with you.

It doesn't record payments for you or touch your books. It reads what has already been recorded, and every accounting or tax decision stays with the person who signs it off, as with every other piece of the system.

Questions and answers

When does the first message go out?

Before the due date, not after. The first message doesn't ask for money: it mentions the invoice, the date and the amount, and asks the customer to confirm everything is in order.

That's when any dispute comes to light while there's still time to sort it out, instead of surfacing thirty days later as the reason the invoice hasn't been paid.

What if the customer has already paid?

They get nothing, because before every send the system checks against the payments recorded and removes anything that shows as paid. The same goes for invoices with an open dispute: they drop out of the automatic sequence and go back to a person.

Chasing someone who has already paid is the quickest way to lose a customer who was doing nothing wrong.

Can we charge interest and recovery costs?

Yes, the law provides for it. EU Directive 2011/7/EU, transposed into Italian law by Legislative Decree 231/2002, entitles the creditor to late payment interest and a fixed sum of €40 in recovery costs, with no formal demand required.

The system calculates these amounts and shows them, but never adds them to a document on its own: asking for them is a commercial decision, and it stays with the person who makes it.

Won't we come across as aggressive with good customers?

That risk is real, and it's why the sequence escalates gradually and is checked against payments. The first two steps are purely informative and mention only the invoice number, date and amount; the tone only changes from the third step on, and every step up is decided by a person looking at that particular customer.

In Italy paying late is the statistical norm, not a sign of bad faith: in the latest Cribis survey, just 43.4% of businesses paid on time.

How do you measure whether it's working?

By the average number of days late on invoices collected, measured before and after over the same period and for the same customers. The second number is the share of due dates that get at least one reminder beforehand, which in many businesses starts at zero.

The third is how many disputes come to light before the due date rather than after, because that's where you see whether the first message is doing its job.

Notes on sources

  1. The 43.4% of Italian businesses paying on time, the 4.1% with serious delays of over ninety days and the comparisons with Denmark, Poland and the Netherlands come from the twenty-second edition of the Cribis Payment Study, covering the last quarter of 2025. It's based on more than 2 billion payment records collected through the company's network in 37 countries: a private study built on its own credit management data, not an official survey, and we say so.
  2. The right to the €40 fixed sum and to late payment interest, the default 30-day term and the margin of at least eight percentage points are in Articles 3, 4 and 6 of Directive 2011/7/EU on combating late payment, transposed into Italian law by Legislative Decree 231/2002. It's a legal provision, so there's no sample. We don't give legal advice: how much to claim and when remains your decision, ideally with your own adviser.
  3. This page doesn't report results achieved for a client, because this piece hasn't yet been delivered to a client. The tests mentioned are functional checks run in a test environment.

The other pieces in this group

Money you're owed that arrives late, or not at all

All the pieces, in the six groups

·The next step

Fifteen minutes, with your case in front of us.

How much money is owed to you right now, and for how many days? If answering that means opening your business software and adding it up by hand, that already tells you the size of the problem. In fifteen minutes on the phone we'll look at it together and tell you where it makes sense to start, even if we never end up working together.

You'll speak to Mattia Esposito, who then builds the system: there's no salesperson in between. If you'd rather measure things yourself before talking, the Diagnostico (in Italian) is twenty questions and five minutes.