How to Automate Invoicing and Chasing Payments

"Chase Dave's invoice (again)." If you run a small business, you've probably had that sticky note on your desk. Chasing money is one of those jobs nobody wants to do, so it gets put off, and the longer it's put off, the longer you wait to get paid.

It's also one of the best jobs to automate. It's repetitive, it follows the same rules every time and it doesn't need to be you sending the first polite reminder. Here's how to set it up.

Step 1: Use what's already in your accounting software

Before you build anything, check what you already have. Most people are paying for features they've never switched on.

If you use Xero or QuickBooks, you can usually:

• Set up repeating invoices for regular customers, so they go out on the same day every month without you touching them
• Turn on automatic payment reminders for overdue invoices, with your own wording and timing
• Add online payment options to your invoices, so customers can pay by card straight from the email

This costs nothing extra and takes about half an hour. For a lot of small businesses, it's half the problem solved.

Step 2: Create invoices automatically

The built-in tools work well once the invoice exists. The gap is usually getting the invoice created in the first place. That's where an automation platform like Make comes in. It connects your accounting software to everything else you use.

Work out what tells you a job's ready to invoice. That's your trigger. For example:

• A deal is marked as won in your CRM
• A job is marked complete in your job sheet or project tool
• A booking is confirmed
• A form is filled in by your team when work is signed off

The automation then goes off and does the rest:

1. Finds the customer in Xero or QuickBooks, or creates them if they're new
2. Creates the invoice with the right line items and amounts
3. Saves it as a draft for you to check, or sends it straight away once you trust it
4. Updates your CRM so everyone knows it's been invoiced

No more jobs slipping through the cracks because nobody remembered to raise the invoice.

Step 3: Chase late payments, with a personal touch

Built-in reminders are fine, but they're the same generic email for everyone. Your best customer who's a few days late gets the same message as the one who's ignored three reminders.

With Make and a bit of AI, you can do better:

1. Every morning, the automation checks for overdue invoices
2. It looks at each customer's payment history: are they usually on time, or do they always need a nudge?
3. AI drafts a reminder to match. Friendly and light for a good customer who's slipped. Firmer and clearer for a repeat late payer.
4. The reminder lands in your drafts for a quick check, or goes out on its own for the first gentle nudge
5. After a set number of days, it flags it to you in Slack, Teams or by email, because at that point a phone call usually works better than another email

AI takes the emotion out of it. You're not writing a reminder while you're annoyed. You're checking a polite, professional draft and hitting send.

Step 4: Close the loop when you get paid

When the payment comes in, the automation can:

• Mark the deal or job as paid in your CRM
• Send a quick thank you, if that's your style
• Ping you in Slack so you get the good news too

It's a small thing, but knowing what's been paid without logging in to check saves more time than you'd think.

What about supplier bills?

The same idea works the other way round. Instead of typing supplier invoices into Xero by hand:

1. Forward bills to a dedicated email address
2. AI reads each one and pulls out the supplier, amount, due date and line items
3. The automation creates a draft bill in Xero or QuickBooks for you to approve

Keep these as drafts. You want to check what's being entered before anything gets paid, and your accountant will thank you for it.

What to keep human

Not everything should be automated. Keep these for yourself:

• Disputes. If a customer says the work wasn't right, that's a conversation, not a reminder.
• Customers who are struggling. A personal call can keep a good relationship going where a third automated email won't.
• Your biggest clients. You might want to handle their reminders personally, even if the automation flags them.
• Anything tax related. Get your accountant to check how invoices and bills are set up before you automate them.

Avoid these mistakes

• Test with drafts first. Run the automation with invoices saved as drafts until you're confident it's getting everything right.
• Watch for duplicates. Make sure the automation checks whether an invoice already exists before creating another one.
• Check the contacts. Reminders going to the wrong person at a customer's business won't get you paid any faster.
• Build one step at a time. Get invoice creation working before you add the chasing.

What it costs

Less than one late payment. Make's Core plan is about $9 a month billed yearly, and an invoicing automation uses a handful of credits each time it runs. The AI drafting a reminder costs pennies. Compare that with the hours spent each month raising invoices and chasing them, plus the cost of waiting weeks longer to get paid.

My advice

This week, switch on repeating invoices and automatic reminders in your accounting software. That's free and takes half an hour.

Then pick the one gap that costs you most, whether that's invoices not getting raised or late payers not getting chased, and automate that first. Get it working, then add the next step.

Then throw away the sticky note.