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.

Then why would the client trust them to do the work?

What you're hinting at here is risk. If you work, deliver, then invoice then you are assuming all the risk.

If you demand 100% up front, then they assume all thd risk.

If you do deposits and partial payments and so on then you share the risk.

Naturally you want to take no risk. Your customer wants to take no risk. It sounds like the original poster here is taking all the risk.

So to the OP I say, treat the money lost as an education. I spent 7 months chasing a tiny amount of money early in my career. It taught me the value of risk.

Lots of companies don't pay invoices on receipt. 90 days is really common. So all is not lost. But the important thing is to understand where you went wrong. Work out the value of the risk, and include it in your price.

I usually specify payment terms when quoting. Changing the payment terms changes the quote.

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.

This is totally correct, and something that took me a long time to learn.

Doing lots of slowly escalating "check-ins" and "reminders" means you are owning the problem, not the other party, and you're teaching them that every time they do nothing, they can expect another "reminder" or escalation that is not much firmer than where they are today. They become like the frog that gets boiled in slowly increasing water temperature.

Instead, I've found it much more effective to have only a small number of very clear interactions. Step 1) ask nicely - say what you need, when you need it - "payment is due in 14 days". Send approximately _one_ "first and final friendly reminder". That's it - if it doesn't work, and the 14 days has come and gone, then switch immediately into thermonuclear asshole mode - call them, show up at their office, hand it over to a lawyer/debt collector, etc, etc. It works best to a clear, contrasting, binary distinction between "asking nicely" vs "not nicely", good cop / bad cop, so that the transition is very obvious and gets a reaction.

> then switch immediately into thermonuclear asshole mode

I can't imagine the number of clients I would have lost over the years if I'd had this approach.

People need time to pay for soft services. Unless you're billing hourly for your time at general labor rates, surely the margins are incredible for what you're doing.

Being a jerk to a client is a surefire way to end that relationship. Some clients who have taken their sweet time to pay over the years are also some of my longest and overall most valuable business contacts. Being a jerk to them would have given someone else a chance to step in and earn their business by providing better customer service.

Invoice dates aren't thermonuclear deadlines and treating them as if they are is shortsighted.

> I can't imagine the number of clients I would have lost over the years if I'd had this approach.

Nonsense. I've been consulting for 13 years. The clients that are always late are routinely the most annoying, those that expect the most for the least, and with rates always below the best paying clients. I can already tell from the first interview what kind of client they are, if they balk at the price or try to micromanage time and expenses, I don't even accept the contract.

If a client is always late paying invoices, asks for discounts or expects me to work for free, I drop them. Has worked wonders. I haven't had a late invoice in like 6 years.

(On the other hand I had a client that texted me sorry whenever he was ONE day late, taking time over the weekend to set up the bank transfer, and he was the best client I've ever had. Stayed with them building up their business for 6 years)

It's simple really: I create good solutions on time, you pay for whatever I ask on time. None of this is negotiable in any way. Shit happens, but needs to be communicated clearly and be an exceptional event, otherwise something's gone wrong.

> I can already tell from the first interview what kind of client they are

I don't think you can tell, but you believe it - if you approach people with this kind of attitude, it is no wonder you have never made it over the hump with someone who actually needs help and is busy with their pressing business and isn't a perfect client

It's great when someone pays promptly, but I'd be a fool to turn my nose up at someone because they take a few weeks to open their wallet and pay an invoice for temporary use of my brainpower to do something for them when they needed my help.

I see clients as human beings with different routines, ryhthms, and even procedures of getting something paid. Just because I mark something on a piece of paper as the day I'd like to be paid for it doesn't mean I'll lose my mortgage and go hand to mouth the day after, and I don't expect a client to call me feverishly worried if they forgot to turn in an invoice until yesterday and the payment will be a few weeks. OK. I run my business & life in a way that doesn't put me in a bind if someone else needs a little time.

Treating people this way allows you to form relationships - which is in and of itself much more rewarding, on a more meaningful level.

I don't value or see a reason to enforce military-like pay schedule with the people that I judge on their... what did you say?

> from the first interview what kind of client they are

I think this says a lot more about you. Usually, this is called stereotyping. It can lead to inadvertent racism, sexism, and biases against those your so promptly judge.

You should be aware that you might be focused on the cheque, which has a finite and set value, instead of the person and relationship you can build with each client - which has an unlimited value.

Plus, as far as we know, we get one chance to live our life. Maybe you could try not treating people like you describe, it might make your one life experience different when you see how other people respond.

> I think this says a lot more about you. Usually, this is called stereotyping. It can lead to inadvertent racism, sexism, and biases against those your so promptly judge.

I love how expecting professionalism from clients, and not allowing them to routinely be late on their obligations, as they do not allow me to come short of mine, in your opinion leads to racism and sexism.

As I have a successful consulting business and happy clients, I have nothing to prove to you and I won't bother commenting further on such inflammatory grounds. Good day.

> I can already tell from the first interview what kind of client they are

Noticed you forgot to respond to this as you quickly ran away from any self-reflection

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).

I have charged clients first before I start. Most in full, some in part.

The question "why would they trust me to deliver?" is a good one. And there are two answers:

1. How you sell will determine their trust level. In my sales deck, I have testimonials, case studies and the outline of our full process. By the end of the presentation, when I tell them the price, they expected $10,000, but it's only $4,000. I ask them to pay the 4k now. Or, pay 2 payments of $2,500.

2. If the prospect asks us to do ALL the work first, then invoice, I say the following: "if we do all the work first, it means that you have no skin in the game. In the past, that hurt my business because people would disappear after my team spent 300 hours working. For that reason, it's not our policy to do all the work first. We have 2 options."

Then, i end off by saying: "if that's a deal breaker, I understand and I will happy send you the plan for what you should do next if you want to go at it without our help"

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.

If you do multiple projects for each client, stall the work you're presently doing for every client that pays late. Let them know upfront that unpaid invoices immediately make you halt all work on the next stages of the client's project.

As for the AI solution you're suggesting, it's probably too easy for people to automate that kind of thing, so it might be a tough sell if you're charging $49 for it. But who knows.

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.

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.

I have only worked as a contractor where I was officially working for a third party company and they had a contract with the client. But I didn’t get paid when I wasn’t on contract and working full time for consulting companies (or departments) where I was a full time employee with benefits and got paid regardless of whether I was on the bench.

Either way, I have never known clients to pay in advance and now I’m high enough up the food chain to know that every company has trouble from time to time getting clients to pay. But that’s never been a “me problem”. The company I work for has sales, accounting and legal to worry about it. I get paid on time regardless. The trade off in getting paid less per hour is well worth it.

I still wonder if most people doing “independent consulting” wouldn’t be better off taking your bog standard enterprise dev job working 40 hours a week or working full time for consulting company.

Great advice above. I can’t emphasise enough how important it is to be in the companies finance system and also to be sending invoices to the right people.

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.

Have you agreed on terms of payment with your client?

Some lessons I learned the hard way:

0. Getting paid is your job. Getting paid is more important than doing the work.

1. Pick better clients. Good clients don't have a problem with paying (and great clients are good clients who have regular work).

2. Be blunt about money. Upfront. Require a retainer as part of your contract. You will avoid clients who never intend to pay.

3. You are not a bank. Your retainer is to be applied against final invoice. You owe the client work. They don't owe you money. If a client says they don't have the money, there's no point in doing the work.

4. People who don't intend to pay will almost always tell you they don't intend to pay before you start the work...maybe a "joke" about not paying or a comment "you are charging too much." It lets them rationalize you had it coming because they gave you a warning. Those aren't jokes or complaints. They are statements of intent.

5. If someone's budget does not match their scope, reduce the scope not your fee. Your job is to solve the problems the client is paying you to solve. It is impossible to be paid for solving the problem of paying you less.

6. When someone doesn't pay, stop working. When they owe you money, don't deliver deliverables.

7. Established business relationships with regular clients, can change some of this...the client you've worked with for years can actually be joking about money because you two have a track record.

Good luck.

> i wait a week

This is not long enough. You can say whatever deadline you want on your invoice, but in reality it will be paid approximately 30-120 days after it gets received by the person responsible for paying invoices at the company you work with.

> two weeks later i’m refreshing stripe like a fool

This is still definitely not long enough. Also, Stripe is extremely risky. One chargeback and you can lose a lot.

> just trying to see if this pain’s real enough that people (like you) would drop around $49/mo for it

No: Invoicing/billing/client contact info is the most important data a small business should keep secure. Further, I would never let an automated system reach out to valued clients on my behalf--ever. I have high standards for apps I give access to my financials/P&L/client list and it would take years of trust and reviews before I'd ever consider something like this.

> i just need to know if this is a real pain

It sounds 100% self-inflicted and easy to solve. If you want to be paid the second work is over, use a system where the funds are escrowed and released upon client approval of the project.

Otherwise, all you need to solve your pain is to build a 90 day runway of funds (at least) so your clients can follow their standard processes for invoice payment.

> you have to get a 90-ish day runway going so you don't feel like people are ripping you off when it's just the way the business world has worked for ages.

100% this. Every self-employed consultant must have plenty of cash reserves. It's not just to keep their personal finances solvent but also to maintain a positive relationship with the client. When consultants brood over invoices taking a few months, that angst spills into the personal relationships with the client and everything goes bad from there.

If OP doesn't have a fully liquid cash buffer (I recommend 6 months worth), or if they don't like that invoices routinely take a few months to process, then consulting may the wrong career choice.

Drop them.

Use escrow