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AI Agents for Invoice Chasing

Automatically detect overdue invoices, draft follow-up emails, and escalate the ones that need attention. No more awkward manual chasing.

01the problem

Chasing invoices is the task every founder knows they should do but keeps postponing. You check Stripe, see three overdue invoices, draft an awkward email, get distracted, and the tab stays open. A week later, you're now 3 weeks overdue and the conversation is harder. Cash flow suffers because follow-up is uncomfortable and easy to forget.

02what the agent does

Every Monday at 9 AM, the agent checks Stripe for overdue invoices. For each one, it checks whether you've already sent a follow-up. Then it classifies the situation (first chase, second chase, or escalation) and drafts the right email for each stage. Polite reminder for the first. Direct and firm for the second. Request for a call on the third. You review and send.

Example output

agent output

Invoice Chase Report — 2026-03-09

ClientInvoice #AmountDue DateDays OverdueClassification
Acme CorpINV-0042$4,500Feb 2413First chase
Beta IncINV-0039$8,000Feb 1027Second chase

Acme Corp — Invoice INV-0042

Classification: First chase

Draft email: Subject: Invoice INV-0042 — $4,500 Due

Hi Sarah, just a quick note that invoice INV-0042 for $4,500 is now 13 days past due. I've attached the original invoice for reference. Could you confirm when we can expect payment? Happy to jump on a quick call if there's anything to discuss on our end.

Try it yourself

Copy these prompts into Claude Cowork. Connect your tools. The agent handles the rest.

01
Weekly invoice chase
Runs every Monday. Drafts follow-ups for all overdue invoices.
Run every Monday at 9:00 AM.

1. Pull all overdue invoices from Stripe (past_due or open, due date > 7 days ago)
2. Check sent emails from last 30 days for any previous chase emails per client
3. Classify each: First chase (no follow-up sent), Second chase (one sent), Escalation (two+ sent)
4. Draft appropriate email for each classification
5. Save report with drafts. Email to me for review. Do not send to clients.

FAQ

Common questions about setting up this agent.

Will the agent send emails to clients without my approval?+
No. The agent drafts emails and sends them to you for review. You decide which ones to send and can edit the tone before sending. Nothing goes to a client without you pressing send.
What if I don't use Stripe?+
The agent can connect to Xero, QuickBooks, or any billing tool that Claude Cowork supports. If your tool isn't directly supported, you can export overdue invoices to a CSV or spreadsheet that the agent reads from your Cowork folder.
How does the tone change between chase levels?+
First chase is friendly and assumes an oversight. Second chase is direct, references the first email, and sets a specific payment deadline. Escalation is professional but firm, requesting a call to discuss. Each level is designed to match what's appropriate for how long the invoice has been overdue.

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Weekly Metrics Reports

Pull MRR, churn, burn rate, and runway from Stripe and your accounting tool every Monday. Formatted, compared to last week, and in your inbox before standup.

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Want this running for your team?

I set up AI agents like this for startup founders. 30 minutes, no strings.

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