When I was a contractor I had set deliverables for projects and written agreement on payments for these milestones. One project might have 5-6 milestones.
95% of the time it worked well and the milestones gave an opportunity to review progress with the client, perhaps even a change of direction. On several occasions it lead to extensions (more features) or new projects in the future.
As a self employed contractor (cloud infrastructure), who got badly burned in the past, the key was to have deliverables which were self contained but still required the next chunk of work to be of any use in the bigger picture.
The financial loss for me was only the most recent deliverable should the client decide to ghost me. I did happen unfortunately.
From my perspective, I liked working on multiple sequential deliverables rather than one final one. I appreciate that infrastructure might be more flexible than other areas and often contractors only have one final deliverable.
It is a real pain, but you are approaching it with the same attitude that is causing it. Don't email gently to "check in". Don't beg. Don't start soft and build up over weeks.
If a payment is late, call them directly that day and be firm. Not mean or harsh, just firm. "Hi, your payment did not come through, please take care of it so I can start working for you again." And then stop working with them until it does.
To answer your question, no. I would never pay for an automated service to email payment reminders. Because emails are ignorable.
I agree with a couple of the other comments here. If I'm doing fixed-price work, I require half of it paid up front, and the other half paid at the time of final delivery and acceptance. If I'm doing time-based work, I require the prepayment of a reasonable amount of that time up front.
It's the best way I've found to reduce the risk of clients stealing from me through non-payment. If they've already paid a significant portion, they're more likely to pay the rest. And even if they don't, at least I got something.
And don't be shy about using the small claims courts if the dollar amount is low enough to allow it. You don't even have to hire an attorney to do that (although you should have an attorney as a matter of good business practice anyway).
Invent a fictitious finance controller for your business.
This “person” can be as angry/obnoxious as needed to get paid. And don’t be afraid to pass debts onto collection agencies - or at least threaten this…
You can preserve your nice relationships with customers - after all, what can you do, finance are a separate department, it’s out of your hands.
I’ve seen problem clients put on prepay only. You just have a talk and say their payment delays aren’t acceptable and they have to prepay if they want to keep working with you.
Forget AI.
You just pay me $500 and tell me country and region the company is, and google debt collection agencies for you.
A few thoughts.
1. Get half up front so they are taking the engagement seriously. Call it a retainer fee if you need to. Proves you’re in their accounting system and that the actual buyer is motivated enough to get you on-boarded and paid so that they can get going on the project. There is nothing wrong with half up front. You’ve got expenses while the project is ongoing. It’s a good way to improve you’re overall cash flow.
2. Accounting people and the people you’re actually working with are almost never the same humans. Make sure you know the exact submission process to get the invoice into your clients accounting system. The larger the company you’re contracting with, the more complex and exacting their processes are likely to be. Very large companies tend to use systems like Coupa, and there’s a learning curve to interacting with them.
3. Make sure you have a PO, and then reference that PO on the invoice. Most accounting folks will ignore requests for payment that feel “blind”. It’s part of their anti-fraud and due diligence. Lots of automated, AI-driven fraud out there. We see fake invoices all the time. Don’t do business on a handshake. Document that buying process, including a signature on a scope of work, quote, or similar document that can serve as a contract.
4. As a small company or indie contractor, you can put terms of service as Net 15, payable upon receipt, or whatever you want. Yes, you need to put something on there…but generally speaking, it doesn’t matter what terms you set, especially to larger companies. They’ll pay you when they pay you according to their own byzantine policies, and their payment terms will override yours. We’ve noticed that the biggest companies tend to pay 90 days + day of the month the invoice was submitted, but have never experienced anything longer than that unless the buyer is going through their own hardships or other shenanigans are afoot.
5. We generally engage with accounting contacts to track down late payments, but will go back to the actual buyer that contracted us and ask for help if a payment gets stuck or the accounting folks are ghosting us. In our experience, the actual buyer is usually embarrassed that an invoice is unpaid and can shake the money loose.
6. Finally…getting paid is a PITA. 100%. But if you can put up with the nonsense of having to track it down, you’re almost certain to get paid…eventually. In over a decade of small business work, we’ve never not gotten paid for an invoice, because we were persistent. But yeah, late payments suck especially if you’re going through tight cash flow.
Hang in there and good luck. I feel your frustration.
Have you agreed on terms of payment with your client?
Use escrow
You are attempting to solve the wrong problem, in my opinion.
Do not see clients who do not pay as clients, but as liabilities. The real solution isn't chasing them with smarter reminders, it is changing how you work.
Take partial or full payment upfront, use incremental milestones, and only extend credit to proven partners with a solid track record.
Chasing money after delivery just wastes time and energy. Protect your work, and time, and sanity, not your clients' excuses.