What happens when payment reminders depend on one person?

Usually there is someone in the admin team with a spreadsheet open. They check which invoices are overdue, look up the contact for each client and write an email. Then they note that it has gone. After a while, that same person can no longer remember who had the second reminder and who has not had any.

The job is simple, but it breaks at the first interruption. A busy spell and the reminders get skipped. A holiday and nobody knows where the list had got to. Meanwhile the invoices stay unpaid, and the owner feels it in the bank account before anyone has found the cause.

There is a quieter cost too. Writing the same email again and again, with small changes each time, is tiring, and the tone drifts depending on the day. One client gets a friendly message and another gets a curt one, and nobody chose that.

Which parts of a payment reminder can be automated?

Anything that follows a rule you can write in one sentence. For example: "if an invoice is overdue and the client has not replied, send the first reminder." An automated process can do the following every time it is due:

  • Read the list of unpaid invoices from your invoicing software or a shared spreadsheet.
  • Check the due date and the status of each one.
  • Prepare the email with the client's name, the invoice number and the amount.
  • Send it, or leave it as a draft for someone to look over first.
  • Record that it went out and on what date.

For this to work, the system has to be able to read your invoices. We connect any tool that has an API, so it is almost always possible. If your invoices live in loose PDFs and in one person's memory, the first step is to sort that out, which is worthwhile even if you never automate anything afterwards.

A well-built automation includes error handling and retries. If the invoicing software does not respond at some point, the process tries again and alerts a person if it keeps failing. That way no reminder goes missing because of a fault nobody noticed.

What should you leave alone?

The conversation with a client who has a problem. When an invoice has been unpaid for a long time, there may be a dispute, a mistake on the document or a difficult situation at the client's company. An automatic email at that point can make the relationship worse.

A useful rule: the system sends the routine reminders and a person handles anything out of the ordinary. For that to work, you need to decide in advance what counts as a special case. It might be invoices with an open query, and those of clients who have said they will pay late. Those invoices stay out of the automatic send from the start.

Collecting money also has a commercial side. Sometimes the owner would rather phone the client personally, because they know them. That call should not be automated, and it does not need to be.

What should you decide before you start?

Four decisions save a lot of back and forth later.

  1. How many reminders go out, and how far apart. A friendly first reminder, a firmer second one and, after that, a person. The gap between them is yours to set, depending on how you work with your clients.
  2. Who receives the doubtful cases. One named person, with a stand-in for when they are away.
  3. The wording of each reminder. Write it yourself, or review it before it is used. It is your voice in front of your clients, and it should sound like you.
  4. Which data goes into the process. Before starting, decide which invoice and client data the system will use. Once that is settled, the rest of the design falls into place.

These decisions are made by talking, before touching any tool, and they carry more weight in the result than anything else.

What does it look like once it is working?

For the person in admin, the kind of work changes. They no longer start the day by checking which invoices need chasing. They open a list of reminders sent, with client and date, and another with the cases that have been passed on for review. They give their attention to the second list and leave the first alone.

For the owner, the information changes. They can see at a glance what is outstanding and which reminders have gone out, without asking anyone. No reminder depends any more on someone remembering.

How to get started

Write down on one page how you chase an invoice today: where the list comes from, who writes the message, what wording they use and which cases they treat differently. With that, we can talk about it in concrete terms.

If you want to check whether your case is a fit, get in touch. We work at a fixed price per project, we hand everything over documented, and the system is yours. If what you describe is not a good candidate for automation, we will say so. You can read more about how we work on the automation page.