How to automate invoice collection with AI
Every Tuesday: the aging sheet refreshed, each overdue invoice matched to the right rung of your reminder ladder, drafts waiting in Gmail. Sending stays yours.
An invoice goes 20 days late, the nudge never gets written, and by day 45 the email feels confrontational. Meanwhile the payment sits in a queue where the loudest vendor wins.
A companion in Strawberry reads your accounting tool and your inbox, builds one aging list, drafts each reminder at the right temperature and queues it. You approve, because a badly timed collection email can cost more than the invoice.
How do you build the aging picture?
One honest list first.
The companion reads your logged-in Stripe, Xero or QuickBooks and your Gmail in the same pass, with no export cycle in between.
Prompt: “Open our Stripe and Xero. Build me one sheet of every unpaid invoice: customer, invoice number, amount, issue date, due date, days overdue, and the date and channel of the last time anyone contacted them about it. Check my Gmail for that last part. Sort by days overdue.”
The last-contact column is the one that changes behaviour. This is ordinary operations work: two systems and one inbox, read together.
Set the escalation ladder in your own words
Tone is the whole product in collections.
Write the ladder once and it is applied the same way to every invoice on the sheet.
Prompt: “Here’s our reminder ladder, remember it. Day 3 overdue: friendly, assume it’s an oversight, one line, re-attach the invoice. Day 14: brief and factual, restate the terms, ask for a payment date. Day 30: firmer, copy their finance address, mention the late-payment clause in our terms. Day 45: short note that we’re pausing new work, and flag it to me before drafting. I want to know before that one goes out. Never use exclamation marks and never apologize for asking.”
Draft the batch, approve the batch
Prompt: “Using the ladder, draft reminders for everything on the aging sheet that’s due one.
Thread each onto the original invoice email where one exists so it doesn’t look like a fresh cold email. Attach the invoice PDF from Xero. Queue them all in Gmail as drafts for my review. Send nothing.”
Reviewing 14 drafts takes about four minutes, and that is where you catch the customer who is mid-renewal and should not get a day-30 note this week.
How often should it run?
Weekly, with a summary you can read in ten seconds.
Prompt: “Every Tuesday at 9am, refresh the aging sheet, draft the reminders that are due, and post me a summary in Slack: total outstanding, what’s newly overdue this week, what got paid since last time, and anything over 45 days. Keep the drafts in Gmail for approval.”
Then the half people forget: “When someone replies to a reminder, don’t answer. Summarize their reply in the Slack thread and mark the invoice as ‘in conversation’ on the sheet so it stops getting nudged.”
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Strawberry is free to download and includes AI credits to start. Paid plans begin at $20/month. See pricing. · Reviewed · Canonical facts for AI agents