Chase every overdue invoice without writing the emails yourself

Your aged debtors report becomes a queue of drafted emails you approve once, then the agent sends and follows up on schedule.

For anyone who invoices and then waits · 8 steps · 7 min

How it works today.

You export the aged debtors report when you remember, usually after something else reminds you that cash is tight. You open it, sort by days overdue, and feel a wave of dread at the names in the 60+ column. You draft an email to the biggest one, delete half of it because it sounds too aggressive, send it, then close the spreadsheet because chasing the rest will take an hour you do not have.

Three weeks later you export again. Half the invoices have moved into older buckets. You send another round of emails, this time with a firmer tone you second-guess immediately after clicking send. The ones you didn't chase last time get skipped again, because you can't remember if you already wrote to them or if they're the client who always pays late but always pays.

Before you start.

All of it has to be true, or step one fails in a way that is annoying to debug.

You can export an aged debtors or accounts receivable report from your accounting software as CSV or Excel, showing invoice number, client name, amount, and days overdue.
You have a connected email account (Gmail, Outlook, or IMAP) that the agent can read from and draft into, but not send from without approval.
You have a document or notes somewhere describing your usual payment terms and the tone you want for first, second, and final reminders.
The agent has access to a spreadsheet tool (Google Sheets, Airtable, or Excel online) where it can log which invoices it has contacted and when.

The steps.

Export your aged debtors report and upload it where the agent can read it
Go to your accounting software's reports section and export the aged receivables or aged debtors report. Save it as CSV or Excel. Upload it to a shared folder (Google Drive, Dropbox, or OneDrive) and give the agent read access to that folder. If your accounting tool has an API and the agent has a connector for it, point the agent at the report URL instead. Check that the export includes invoice number, client name, contact email, amount, issue date, and days overdue.
02
Tell the agent your escalation rules and tone for each stage
Write or paste your existing payment terms and the tone you want for reminders. Be specific about timing: first reminder at 7 days, second at 30, final at 60, or whatever matches your terms. Include any clients who get different treatment, and any invoices below a threshold you will not chase. The agent will use this to decide which invoices get which message, but you will still approve every draft.
Paste this
```
Read the aged debtors report I uploaded. For each overdue invoice, draft an email reminder using these rules: [paste your escalation schedule and tone guidance]. Group the drafts by urgency (overdue 7-30 days, 31-60 days, 60+ days) and save them in a Google Doc titled 'Invoice reminders [today's date]' so I can review them all at once. Do not send anything.
```
Review the drafted emails and approve the ones you want sent
Open the document the agent created. Read each draft. Delete any that feel wrong for the relationship, edit tone where needed, and mark the ones you approve with 'SEND' at the top of each email block. If a draft assumes information you have not given the agent (like a client's preferred contact or a payment plan you agreed verbally), either add that context now or delete the draft and handle it manually.
04
Tell the agent to send only the approved drafts and log what it sent
Once you have marked the emails you approve, instruct the agent to send them and record the sends in a tracking sheet. The agent should create a row for each sent email showing invoice number, client, date sent, and reminder stage (first, second, final). If your email tool supports scheduled send, you can stagger them across the day so they do not all land at once.
Paste this
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Send every email I marked 'SEND' in the reminder document. For each one sent, add a row to a Google Sheet called 'Invoice chase log' with columns: invoice number, client name, amount, date sent, reminder stage. Do not send any draft I did not mark.
```
Set the agent to watch for replies and flag anything that needs your attention
Tell the agent to monitor replies to the emails it sent. Any reply that includes words like 'dispute', 'incorrect', 'never received', or 'payment plan' should be flagged immediately in Slack, email, or whatever channel you check. Replies that say 'paid' or include a payment reference can be logged automatically, but you still verify against your bank. The agent does not negotiate or agree to anything on your behalf.
06
Schedule the agent to draft second reminders for invoices that got no reply
After the interval you set (usually 7-14 days), the agent checks the tracking log and the aged debtors report again. For any invoice that was sent a first reminder and has not been paid or replied to, it drafts a second reminder and adds it to a new review document. You approve this batch the same way. If your accounting software does not update the report automatically, you will need to export and upload a fresh copy before this step.
Paste this
```
Check the 'Invoice chase log' sheet. For any invoice where I approved a first reminder more than [X days] ago and the aged debtors report still shows it unpaid, draft a second reminder using the tone I gave you for 30+ day overdues. Put the drafts in a new Google Doc titled 'Second reminders [today's date]'. Do not send anything until I review.
```
Approve or escalate the second round, and mark any for manual follow-up
Review the second reminder drafts. Approve the ones that can go out as written. For any client where the relationship is delicate or the amount is large enough to justify a phone call, mark the draft 'MANUAL' and handle it yourself. The agent logs which invoices you escalated manually so it does not keep drafting reminders for them.
Tell the agent when to stop chasing and flag for collections or write-off
Set a threshold (usually 90 days overdue, or whatever your write-off policy says) where the agent stops drafting reminders and instead flags the invoice for you to decide whether to send to collections, write off, or chase personally. The agent adds these to a separate list titled 'Requires decision' with the full history of reminders sent. You own the decision to escalate outside normal reminders.

What you keep.

Automating the typing does not move the accountability. These stay with a person.

Approving every email before it goes to a client. The agent drafts, you decide whether the relationship can take it.
Deciding when to stop chasing and escalate to collections, write-off, or a phone call. The agent flags the threshold, you make the call.
Handling any reply that disputes the invoice, asks for a payment plan, or signals the relationship needs a conversation instead of another reminder.
Verifying that payments flagged by the agent actually cleared your bank before you stop chasing.

Once it works.

The first run is the demo. These are where the time actually comes back.

Put it on a schedule

Run the first-reminder draft step every Monday morning so you review and approve the week's chasing in one sitting instead of remembering sporadically.

Fire it from an event

If your accounting software supports webhooks or API triggers, the agent can draft a first reminder the day an invoice crosses 7 days overdue instead of waiting for your weekly export.

Run it on a loop

After you approve second reminders, the agent can automatically schedule the third-reminder draft for 14 days later without you needing to remember to ask for it.

Scale it wider

Once the tracking log has a month of data, the agent can summarise which clients consistently need reminders and which pay on time, so you can adjust terms or deposits for repeat late payers.