The answer
Largely. Building the overdue list, sending polite reminders on a schedule and logging promises to pay are almost fully automatable today. In our model about 65% of chasing time can go to software. What stays human is phoning long-overdue accounts and deciding when to pause work or escalate, because those are decisions about a relationship.
The tasks, and how much of each is automatable today
Six tasks make up chasing overdue invoices. Running the aged list and sending scheduled reminders are 95 to 100% automatable. Logging promises to pay is mostly automatable. Answering replies is about 45% automatable, since many are 'please resend'. Phoning late payers and deciding on escalation stay human, and they recover the hardest money.
| Task | Min / week | Automatable |
|---|---|---|
| Run the aged receivables listA standard report in every accounting system, readable by API. | 20 | |
| Send staged remindersTemplated by stage and sent from a real inbox. A person reviews the sequence monthly. | 120 | |
| Log promises to pay and update notesAI pulls the date from a reply and sets a check. Promises made on calls still need logging by the caller. | 30 | |
| Answer replies about missing invoices, POs or small disputesResend and 'which invoice' replies are automatable. Disputes about the work go to the account owner. | 60 | |
| Phone long-overdue accountsSoftware builds the call list. The call, finding out what is really wrong, is human. | 60 | |
| Decide on holds, payment plans or collectionsA rule can suggest a hold at a set age. Weighing the relationship against the debt is the owner's call. | 20 | |
| Whole process | 310 |
Hours saved per week
For a B2B business with about 15 overdue invoices at any time, chasing takes about 5 hours of a bookkeeper's week by hand. Automating the tasks above returns about 3 hours a week, roughly 145 hours a year. The time left goes on the phone calls that actually recover long-overdue money.
Modelled on: A B2B services firm with about 60 open invoices, around 15 of them overdue at any time, chased by a part-time bookkeeper.
- About 15 overdue invoices, each getting around two reminders a week by hand at 4 minutes each.
- Replies (resend requests, wrong PO, small disputes) take about an hour a week.
- A handful of long-overdue accounts get a phone call each week.
- Escalation decisions take about 20 minutes a week.
Tools that do the job
Your accounting software already knows what is overdue. Xero and QuickBooks have basic built-in reminders. For more control, n8n or Make read the aged list, send staged emails from Gmail, sort replies with an AI agent and post anything difficult to Slack. Stripe payment links make paying one click away.
- Xero
- Source of the aged receivables list; has built-in reminder emails for simple cases.
- QuickBooks
- Alternative accounting system with the same overdue data and reminders.
- n8n
- Runs the staged sequence, pauses on reply and builds the call list.
- Gmail
- Sends reminders from a named person's inbox so replies reach someone.
- AI agent
- Sorts replies into resend, promise to pay, dispute or other, and pulls out promised dates.
- Stripe
- Payment link in every reminder so paying takes one click.
A simple workflow
The workflow runs daily against the accounting system. Each overdue invoice moves through stages: a friendly note just after the due date, a firmer one a week later, then a task for a person to call. Replies pause the sequence, and any promise to pay is logged with a date to check.
- TriggerRun daily against all open invoices past their due date.
- StageDay 1 after due: friendly note with the invoice and payment link. Day 8: firmer note naming the amount and days overdue.
- PauseAny reply pauses the sequence. Resend requests are handled automatically; others go to Slack.
- PromiseIf a customer promises a date, log it and check the day after. Resume the sequence if unpaid.
- EscalateAt 21 days overdue, create a call task for a person with the full history attached.
Keep these human
- The call to a long-overdue customer. People pay people, and a call surfaces the real problem.
- Decisions about pausing work, offering a payment plan or using collections.
Where it goes wrong
- Chasing paid invoices. If payments are not reconciled daily, customers who paid get reminders. Reconcile before each run.
- Ignoring replies. A reminder sent after a customer explained a dispute damages the relationship. Pause on any reply.
- Sending from no-reply addresses. Reminders that cannot be answered get ignored. Send from a named person.
What most guides miss
Most reminder guides focus on wording. The bigger lever is order: reconcile payments before reminders go out, and stop the sequence the moment a customer replies. Automated chasing fails worst when it reminds someone who already paid or ignores a dispute they raised, and both are data-timing problems, not copywriting problems.
The evidence
- Average cost to process an invoice is roughly $9.40 to $9.90, against about $2.70 for best-in-class teams.Ardent Partners, The State of ePayables 2024: Money Never Sleeps (2024)
- Interacting with stakeholders has a technical automation potential of 20%, compared with 69% for processing data.McKinsey Global Institute, A future that works: Automation, employment, and productivity (2017)
“Automation applied to an inefficient operation will magnify the inefficiency.”