Automate your chase late invoices without chasing people who already paid
Chasing late payments is a job nobody wants and everybody forgets. As a standing job, one department pulls the invoices that are past due, another drafts a reminder suited to how late each one is and who the customer is, and a second pass checks every draft against the books so you never chase someone who already paid. You approve what goes out.
By the Organ team · Last verified 2026-10-30
What the job is
A morning list of overdue invoices with a drafted, checked follow-up for each. Nothing goes out until you approve it.
Usually the founder, a bookkeeper or a virtual assistant. Someone opens the accounting tool or the payments dashboard, sorts by due date, copies a name into an email and writes the same polite note for the tenth time. It happens when there is time, so some invoices get chased at day 3 and others at day 40. The awkward part is tone: the same message goes to a long-standing customer and to a new one, and now and then a reminder goes to someone who paid yesterday. Some payment tools can send scheduled reminder emails on their own, which covers the plain case. The human work is the judgement around it.
How the departments split it
- OperationsUses read access to your invoicing or accounting tool, through an integration written against its API or MCP server. Lists invoices that are open and past their due date, with customer, amount remaining, due date, days late and any earlier reminders already sent.
- MarketingDrafts one follow-up per invoice, matched to the stage you set in the fields: a friendly nudge for a few days late, a firmer note for the second stage, a final notice for the last. Uses your tone and your payment link, and writes it as a short message from a person.
- OperationsChecks each draft against the records before you see it. Rereads the invoice to confirm it is still unpaid, that the amount and due date in the message match, that the customer is not on your exclusion list, and that no reminder already went out inside your minimum gap. Drafts that fail are pulled and the reason is noted.
- StrategyHands you the checked drafts with a short summary: how many invoices, how much is outstanding and which are the oldest. You approve, edit or skip each message. Nothing is sent to a customer until you do.
What you get
Sample, not live data. The company, customers and amounts below are invented to show the shape of the daily list. Drafts are written by AI.
"Nothing is sent to a customer until you approve it."
Overdue invoices: 3 ready, 1 pulled, $4,550 still outstanding
| Customer | Invoice | Amount left | Days late | Stage | Draft |
|---|---|---|---|---|---|
| Harbor Print Co. | INV-1042 | $1,200 | 4 | Nudge | Ready |
| Lumen Dental | INV-1031 | $2,450 | 17 | Firm | Ready |
| Fernwood Studio | INV-0998 | $900 | 34 | Final | Ready, review tone |
| Cobalt Logistics | INV-1019 | $1,600 | 21 | Firm | Pulled |
Before: the plain reminder
"Your invoice is overdue. Please pay now." Same text for every customer, the original total, no check that the invoice is still open.
After: the checked draft for Harbor Print Co. (nudge)
"Hi Dana, a quick note that invoice INV-1042 for $1,200 was due four days ago. If it is already on its way, please ignore this. The payment link is below if that is easier. Thanks, Sam"
Checked by operations
- INV-1019 pulled: the books show a $1,600 payment received this morning, after the list was built.
- INV-0998: the amount left is $900, not the $1,500 on the original invoice. The draft was corrected to the amount still owed.
- Lumen Dental was last reminded 9 days ago, longer ago than your 7 day minimum gap, so the draft is allowed.
Worth your eye
Fernwood Studio is 34 days late and has been reminded twice. A call from you may land better than a third email.
How it would run
- Department
- Operations
- Runs
- daily
Every morning at the time in the fields, read the invoicing or accounting tool named in the fields and list invoices that are open and past their due date, leaving out any customer in the exclusion field and any customer reminded within the minimum gap. For each, draft a short follow-up from a person in the tone given in the fields, matched to how many days late it is: a friendly nudge, then a firmer note, then a final notice, using the day thresholds in the fields. Ask another department to check every draft against the records: invoice still unpaid, amount owed and due date correct, customer not excluded, reminder gap respected. Pull any draft that fails and say why. Bring me the checked drafts with the count, the total outstanding and the oldest invoices. Send nothing to any customer and change nothing in the accounting tool until I approve each message.
You can change: Invoicing or accounting tool, Customers to leave out, Minimum days between reminders to one customer, Time the list should be ready
Add this job to my companyQuestions
Does it send emails to my customers on its own?
No. It drafts the follow-ups and brings them to you. You approve, edit or skip each one, and nothing is sent until you do.
How is this different from the reminders my payment tool already sends?
Stripe, for example, can send reminder emails before, on or after the due date for invoices you send to customers, on a schedule you choose. That handles the plain case. This job adds the judgement around it: a different message for each stage, a check that the invoice is still unpaid and the amount is right, an exclusion list, and a person approving what goes out. It also works for invoices in tools that have no reminder feature.
How does it know which invoices are overdue?
It asks your invoicing tool for open invoices and compares each due date with today. In Stripe, for example, the list invoices call accepts a status of draft, open, paid, uncollectible or void, and invoices you send to customers carry a due date. Any other accounting or invoicing tool with an API or MCP server works the same way: the team builds the connection for you, and you supply read access.
How do you stop it chasing someone who already paid?
A second department rereads each invoice just before you see the draft, and pulls any that are now paid or partly paid. The amount in the message is the amount still owed, not the original total. You also see the list, so you can spot a mistake before approving.
Can I keep some customers out of it?
Yes. Put them in the exclusion field and they are left out of the list. You can also set a minimum number of days between reminders to the same customer.
Does it change anything in my accounting tool?
No. It reads invoices and writes drafts. It does not mark anything paid, void invoices or change amounts.
Sources
- Stripe docs: Automatic collection and invoice reminders (reminders before, on or after the due date) · docs.stripe.com · retrieved 2026-10-30
- Stripe docs: Send email receipts and reminders (reminders for recurring invoices) · docs.stripe.com · retrieved 2026-10-30
- Stripe API reference: List invoices (status filter, due_date, collection_method=send_invoice) · docs.stripe.com · retrieved 2026-10-30