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I've been doing multiple month-long contracts for a client as a software engineer, and the CEO is regularly late with payments despite me raising this concern. It's gotten to the point where I don't know what to do further about it and I am considering just stopping doing work with them after my current contract is done. I'm not sure what I can say even further without being pushy, since I've sent several reminders for various invoices. They do get paid, just late and it's a distraction to have to deal with them being late.

They recently closed a round of funding so it's unlikely a cash flow issue.

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    "I'm not sure what I can say even further without being pushy" Why do you wish to avoid being pushy when they're screwing you over? Sep 25 at 11:20
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    A client that doesn't pay is worse than no client at all. It may be time to move on.
    – jwh20
    Sep 25 at 11:49
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    What is late? Is it by your definition, or does your client have standard terms and conditions on when they pay? My clients (large companies) have standard 60 day terms on accounts payable, and there is no way I can change that.
    – Peter M
    Sep 25 at 15:05
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    Every business I've ever worked with has been exactly 30 days overdue after the due date that was already generously set 30 days into the future from the invoice date. They do it intentionally. Its annoying enough that I almost refuse to work off of invoice, or demand higher rates on projects that do it. Unfortunately that's part of the game. If I were you I'd just charge 20% more on these, then get a credit line to cover the floated amount
    – schizoid04
    Sep 25 at 18:35
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    21 days "after expected". Expected based on what? How many days did you think they were going to take to pay you? Most likely your expectations of the speed of corporate finance departments is way optimistic. While some indeed pay promptly (my current project for example tends to pay within 2 weeks of the end of each month) most are slow as molassus. Several I've encountered in the past set their payment term themselves as 60 days past the end of the month in which you billed them for example, and often were slower than that. one managed to delay by 6 months and get angry when called out on it
    – jwenting
    Sep 28 at 12:51
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There are a couple of different options you can take:

  • You can have penalty fees for late payment (which may be limited by the laws in your country). However, depending on the power relationship between you and the client, you might struggle to enforce these.
  • You can involve a third-party legal/debt collection agency. A letter from them usually gets things sorted quickly - but this is a somewhat nuclear option, and may end up losing you the client.
  • You can offer an incentive for prompt (or even early) payment. Push up your prices by 10%, and then offer a 10% discount if the invoice is settled within a defined period. Or longer-term incentives like offering a discount/free stuff if they pay a certain number (or percentage) of invoices on time.
  • You can try and break up the work into multiple chunks, which are invoiced separately, and add some terms saying that if an invoice becomes overdue by more than X days then you stop working until it's paid.
  • You could look at using Factoring, where you essentially sell your invoices to another company, and then it's their job to collect payment. They'll take a cut though, so you're basically trading a percentage of the invoice for reliable payment.
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    A self-employed mechanic friend did the "bump up and quick pay discount" 15% added on top to the original invoice. Most customers paid in the seven days and were regulars as he was and still is a good mechanic. The one who paid later paid...
    – Solar Mike
    Sep 25 at 15:25
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    @SolarMike OT, but right now I am dealing with a home remodeler, who I suspect bumped his prices up in order to offer me compensation after the fact for the bad product that he knew he was going to supply.
    – Peter M
    Sep 25 at 16:23
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    There is also the "stop work until past invoices are paid."
    – David R
    Sep 26 at 14:36
  • Option 3 (discount for timely payment) is an extremely common practice in Europe. It's basically the same as Option 1 but frames it as an incentive instead of a penalty. Usually, Option 1 with a longer deadline (after which the client is considered in default of payment) is used additionally.
    – Roland
    Sep 29 at 5:44
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I have 2 strategies when this happens. You have already used most of the first which is to push for timely payments.

My second strategy (if I don't just drop them) is to double my price. I don't mind waiting if I'm paid enough.

If you use this strategy, don't bluff, make sure you are prepared to decline further work.

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  • @JoeStrazzere because I have a set rate which I'm happy with. No need to get greedy on everyone all the time.
    – Kilisi
    Sep 26 at 21:12
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My whole life, in sundry industries and fields, I've only ever worked on the basis 1/2 in advance. Maybe that philosophy will help.

Regarding the particular client you describe, as everyone has said, forget them and never work for them again.

Everyone gets a scum client from time to time. Forget about it and move on.


Also in this particularly case,

been doing multiple month long contracts for a client as a software engineer

A simple solution is to state that you wish to be paid on a weekly breakdown ("with money wired each Friday") as payment structure for the project.

If the money doesn't arrive in your bank on Monday morning, put your tools down, ghost them, and write off the one week as a loss, and start looking for your next project.

(If they "come good", literally ghost them until the money arrives in your account from that week and however many weeks have passed.)

So, "regular payments" (ideally every week, possibly every two weeks, but never longer that that) are the practical solution to you actual problem.

(Note that if a potential client "has trouble" with that financially - they're not a client. Just walk away.)

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    1/2 wouldn't work in this case. When you know the person has a record of not paying on time, you need to ask for 100% upfront. Tell them. You're just like family. One of my family members never pays me on time. So I'll have to tell you what I told him. you'll need to pay $5,000 upfront and you'll need to keep that amount regularly replenished because if the remaining amount falls below $3,000, I can't accept any new work from you. Sep 25 at 19:55
  • really! Me or my companies have never worked for a family member. I'd say, sure, getting paid 100% up front, before starting work, is (of course!) ideal. I've only ever been able to pull that off a couple times. Realistically the OP won't be able to do that.
    – Fattie
    Sep 26 at 14:39
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    If they refuse, which is likely, it's just like you said, you walk away, and they hire someone else. Also, I'm not suggesting you do this for everybody, but only for the people that have a track record of not respecting your boundaries (or other people's boundaries). It's an abundant world out there. Sep 26 at 18:15
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You're giving them bills, those bills go to an accounts payable department, and then you get paid like you're a company.

So either there is someone whose job it is to pay you late (i.e. in 90 days), or you get paid when a stack of other bills get paid.

Billing them more often won't fix this, if bills get paid once a month (or every other month, or once a quarter), then you'll just get a brick of payments all together.

You've made it clear that the cashflow of this is a problem for you.

You've also made it clear that asking them to not treat you like a company doesn't work.

You have three options.

  1. Live with it, and manage cashflow with loans and/or putting "pay +X% more if late" charges in there.

  2. Refuse to work with them.

  3. Get a middleman who will pay you on a regular basis (i.e. as a human) and worry about the cashflow themselves. Just call around for some job shops and tell them you need someone to cut you a check for your work but you're getting "$X".

#3 is not a cheap option and your rates will effectively go up, but the group you're dealing with WANTS to pay you like a company so maybe they'll go for it.

Maybe you can also sneak in a price increase too.

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When you make a contract with a client, then there are a couple contract clauses you can insist on to ensure on-time payment of your invoices:

  • Positive reinforcement in form of an early payment discount. Which means your client saves money when they pay before a certain date.
  • Negative reinforcement in form of dunning fees and dunning interest. Which means your client pays extra when they pay after a certain date.
  • Gun to their chest in form of a contract clause which prohibits them from benefiting from your work when they don't pay. A common clause in contracts for creative work is "copyright transfer on payment in full". Which means when the client uses your work while they still have outstanding bills, they are violating your copyrights. Which opens them up to legal consequences.

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