Guide
How to stop chasing unpaid invoices
Let an AI agent do the chasing and keep the sending for yourself. It finds what's past due, drafts the reminder, and waits for you to hit send.
Video, 42 seconds. Transcript below. Watch on YouTube
Why invoices slip
Chasing money is awkward, it's repetitive, and it loses to everything else on your list that feels urgent. The reminder that never got written is often why a paid job sits unpaid for another month. The fix isn't trying harder. It's taking the writing off your plate and keeping only the decision.
How the agent handles it
- It checks on a schedule you set. Every morning, or every Monday at 7 AM. It starts on its own, on your computer.
- It reads your email for open invoices that are past due.
- It drafts a polite, firm reminder for each one. The longer an invoice stays unpaid, the firmer the next reminder gets.
- Nothing goes out until you approve it. You review the stack with your coffee, fix anything you want, and hit send.
A simple reminder schedule to start with
This is a starting point, not a rule. Adjust it to how your customers actually pay.
- A friendly note a few days after the due date.
- A firmer note about a week later, with the invoice attached again.
- After that, a phone call from you. Some accounts need a person, not another email.
Why it shouldn't send on its own
You know things the inbox doesn't. The client who's paying late might be the one you talked to yesterday, the one disputing a charge, or the one who always pays on the 15th. An automatic form letter to the wrong person costs more than the late invoice. So the agent writes, and you decide.
Questions owners ask
Do I need new invoicing software?
No. The agent works from your email and the files you already use. If your invoicing app already sends automatic reminders, keep them. The agent covers the follow-ups that need your tone and your judgment.
Will it send a reminder without asking me?
No. Anything that sends, spends or deletes waits for your OK.
What does it cost?
A Professional install starts at $2,500. Every install includes the first 30 days of the Care Package free; keep it after that for $195 a month if you enroll. You also pay Anthropic directly for your Claude subscription. Full details are on our pricing page.
What computer do I need?
A Windows computer you own that can stay on. Mac isn't tested yet.
Video transcript
How do you stop chasing unpaid invoices? Let an AI agent do the chasing, but keep the sending for yourself. On a schedule you set, it reads your email for invoices that are past due and drafts a polite, firm reminder for each one. The longer an invoice stays unpaid, the firmer the next reminder gets. Nothing goes out until you read it and approve it, so a client you're already talking to never gets a form letter. You review the stack with your coffee and hit send. Cash stops sitting in someone else's account. CommandKey installs an agent that does this on your own computer, with your own email. Get a free week audit at commandkey.ai.
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