Money

Invoice reminders that get firmer as invoices age

Twice a week, Cowork reads the QuickBooks aging report and writes a reminder draft for each overdue invoice, polite at 7 days and firmer at 30 and 45, skipping anyone on the owner's exceptions list.

For: Most trade shops and small officesBy John DietrichUpdated

The problem

Chasing money is the job everyone puts off. The owner doesn't want to sound desperate, the office manager doesn't want to annoy good customers, and so invoices drift past 30 and 60 days. A steady, polite reminder routine collects more than an occasional angry one.

What Cowork does

  1. A task on Tuesday and Friday mornings reads accounts receivable aging from QuickBooks through Intuit's official connector.
  2. For each overdue invoice it picks a tone by age: friendly at 7 days, direct at 14, firm at 30, and a final notice draft at 45 that the owner must approve personally.
  3. It skips customers on an exceptions sheet (payment plans, disputes, friends of the owner).
  4. It writes Gmail drafts that include the invoice number, amount and payment link.
  5. Friday's run adds a cash summary for the owner: total overdue, what was reminded, and what came in since last week.

Where the draft lands

Gmail drafts labeled AI-draft and a Friday summary email.

What stays with you

Sending reminders, payment plans, collections agencies and liens.

Gmail draft (14 days)Example · Brightline Electric is fictional

Hi Tom, a reminder that invoice 3317 for $1,240 (fixture install, Sep 18) is now two weeks past due. You can pay here: [payment link]. If there's a question about the work or the invoice, just reply and Mel will sort it out. Thanks, Sam

Watch-outs

  • QuickBooks can send its own reminders. This idea is for shops that want reminders that read like a person wrote them.
  • Keep the final-notice step manual. Anything that mentions collections or liens should come from the owner.

Questions owners ask

Can it send the reminders itself?

The Gmail connector can send, but sending needs approval by default. Drafts keep a person in the loop.

What about Xero?

Xero's official connector is read-only, which is enough to read aging and write Gmail drafts.

Connector capabilities checked October 2026 against Anthropic and vendor documentation; they change, so confirm before you buy anything. Workahead is independent and not affiliated with Anthropic.