Agent skills for chasing unpaid invoices
A chase skill drafts the follow-up you keep putting off. It reads the invoice number, the amount and the due date out of your own client file, works out which reminder this is, and matches the tone to the attempt. It does not set your terms, it does not threaten a consequence you have not agreed to, and it never sends anything.
The four facts it needs before it writes
Chasing money is an admin job that feels like a relationship job, which is why it slips. Give the skill these four things once and every reminder after the first is a thirty-second task.
The invoice itself.
Number, amount, date issued, date due. All three of the last ones go into every draft, including the friendly first one, because a client who has to go looking for them replies asking instead of paying.
What you have already sent.
A line per previous reminder in the client file. This is the only thing that sets the tone. Without it the skill writes a first reminder for an invoice you have chased twice, which reads as though you were not paying attention.
Your payment terms, in writing.
Net 14, net 30, whatever you agreed, plus anything the contract actually allows you to do about a late one. A skill will not invent a late fee, and it should not: a consequence that is not in the contract is one you cannot apply.
How you sign off.
Short and consistent. A chase that sounds like a different person than the project emails is the one that gets forwarded to a finance inbox and lost.
Tone is a function of the attempt, not of your mood
The useful part is not the writing. It is that the same rule applies on a Tuesday when you are relaxed and on a Friday when payroll is close, so the escalation stays even and the client never gets a jump they did not earn.
- First, a few days over. Assume it was missed. Two lines, no mention of terms, invoice attached again.
- Second, around two weeks over. State the facts, restate the terms, and ask for a payment date rather than for payment. A date is something a client can answer.
- Third, around a month over. Name the consequence that is genuinely in the contract and that you are willing to apply, ask for a reply by a specific day, and offer a payment plan on its own line.
- Fourth and beyond. Short, formal, no warmth padding. States the next step and the date it takes effect, and tells you plainly that this one changes the relationship.
> chase the Calder invoice, they still have not paid
reading: memory/clients/calder-group.md
previous reminders logged: 1 (2026-08-14)
terms: net 30, due 2026-08-05Attempt 2, 24 days past due. Tone: firm, not formal.
Subject: Invoice 0142, <amount>, due 5 August
Hi Dana,
Invoice 0142 was due on 5 August, so it is now three weeks
past our net 30 terms. I sent a reminder on 14 August. Copy
attached again in case it went astray.
Can you give me a payment date? Even an approximate one
means I can stop chasing.
Bank details are on the invoice.
Best,
Sam
If they do not reply
Third reminder on 9 September. That one names the pause on
new work and offers a payment plan.What it does not do
- It does not send. Every draft lands in front of you first, every time, without exception.
- It does not threaten. A late fee, a formal notice, a third party: these come out of your contract, and if you have not raised one it appears nowhere in the reply.
- It does not know whether the client is broke or annoyed. It writes the letter that finds out, which is why the payment-plan line is a required part of the third attempt and not a judgement call.
- It does not track anything on its own. The reminder log is a file you keep. If nobody writes in it, the tone drifts back to friendly and the escalation resets.
The one thing that makes it fire reliably
Nobody types the word chase. They type "Acme still has not paid", "second reminder for Calder", "how do I ask for money without being rude", or just "final notice". If the skill's description names only the tidy phrasing, the messy ones miss it and you write the email yourself again. Put the words you actually use into the description. There is a full guide on writing a description that gets picked.
Works with Claude Code.
The Agency Owner pack
Fourteen skills for the work an agency repeats: briefs, proposals, weekly client reports, invoice follow-up, scope-creep checks. The chase skill ships with the client file it reads, so the reminder count is somewhere other than your head. The eval files ship with it too, and the pack page carries the price and the refund terms.
See the pack