One of the things I try to keep up with is to keep my finger on the pulse of the companies and people I deal with. My software lets me know as soon as someone goes over 30 days, and 60, 90 are the next waypoints. I try to get in touch with customers and find out why they are late.
Some are just lazy procrastinators, others have a 45 day billing cycle, sometimes the bill gets misplaced or lost in the mail. I guess I'm lucky or blessed because after 24 years in business, I've only been cheated out of less than $1000 total. There have been a few times where I thought there were going to be issues but a phone call to the right person and the issue was resolved and a check was cut.
The longer a customer is allowed to not pay, the harder it then becomes to eventually collect. Since I don't know all the details.... if you were to stop providing your service or product to them would that make any difference to them or is it not possible to do that? That is my leverage.... I cut off the service and lock them out until I get paid. I've not had to do that very often. Just the threat of doing that often gets a check in my hands quickly.
If I had a customer like the one you describe, I'd probably seek the services of either a collection agency or a lawyer or some combination thereof. They will take a sizable chunk of what they collect, and it might not be the full amount. They will very likely negotiate a settlement and they will keep 30% or more of the money they collect. However, having part of that is better than having none of that..... and remember that if you are on speaking terms with their accounting dept, you could negotiate that kind of a deal too and keep 100% of the settled amount. It's always better to settle things like this and get some money.
Would they suffer if you stopped doing business with them? And the flip side is that if you go after them with a collector, they will very likely not do business with you. So be prepared to lose a customer. Taking them into court, if it becomes necessary, might, depending on the laws in the state, allow you to sue for additional damages and punitive costs as well as legal fees, in addition to and above the full amount owed. Most lawyers and collection agencies will discuss this all in detail with you for free. That way, you can make a better decision than that based on what advice you get here.
I heard this on Clark Howard's money show.... regarding being let out of or forgiven a debt or a settlement amount. If they don't pay in full, or agree to a settlement, you can always send them a 1099 form so that what they don't pay you becomes to them, taxable income. Of course that's like burning your bridges.
Yeah, check with a business lawyer in your state. Many will work on a percentage basis.