By KYN AI Advisory Team — AI implementation specialists, Singapore
We built a receivables chase agent that works a three-rung ladder: a reminder at 3 days overdue, a firmer note at 14 days and an escalation at 30 days. The agent drafts each message, checks that the invoice is still unpaid and not disputed, and queues the draft for a named person to send. It runs on KYN's own books. This article describes the ladder, the stop conditions, the tone at each rung and what we kept out of the agent's hands.
The point of a ladder is not to chase harder. It is to chase on time, every time, without anyone remembering to do it.
Why a ladder instead of one reminder?
Late payment has different causes at different ages.
- Around 3 days late: usually an oversight. The invoice went to the wrong inbox, the approver was away, the payment run missed it.
- Around 14 days late: the invoice is stuck somewhere, or there is a question the customer has not raised.
- Around 30 days late: it is a problem. Either a dispute, a cash issue or a decision not to pay yet.
One message cannot fit all three. A ladder gives each age the right tone and the right owner.
The timing of 3, 14 and 30 is our setting. It is a parameter, and each client sets their own, based on terms and customer type. A business on 60-day terms with large customers will use different rungs from a retailer on 7-day terms.
What does each rung do?
| Rung | Trigger | Tone | Content | Who sends | |---|---|---|---|---| | 1 | 3 days overdue | Neutral, brief | Invoice number, amount, due date, payment details, a link to the invoice | Named person approves | | 2 | 14 days overdue | Direct, polite | Same, plus the earlier reminder, and a request for a payment date | Named person approves | | 3 | 30 days overdue | Formal | Same, plus the history, and a note that the account owner will call | Account owner reviews, then sends or calls |
Rung 3 is as much a task as a message. The agent drafts a note and also opens a task for a person to phone. Money that is a month late needs a conversation.
What are the steps?
- Read the open invoices. The agent lists unpaid invoices from the ledger and their due dates.
- Reconcile with the bank. It checks whether a matching payment has arrived but is not yet applied. This avoids chasing a customer who has paid.
- Check the stop conditions. Disputed, on hold, payment plan agreed, or the customer has asked not to be contacted.
- Find the contact. It uses the billing contact on the invoice, not the sales contact.
- Draft. It writes the message for the right rung from a template and the invoice facts.
- Queue. The draft goes to the review queue.
- Send and log. After approval, the system sends and records the message, the approver and the time.
- Wait and re-check. It checks again on the next day. A reply or a payment moves the invoice out of the ladder.
The message text is a template with fields filled in, plus short wording the model writes to suit the situation. The facts, such as amount and dates, come from the ledger, never from the model.
What stops the ladder?
Stop conditions matter more than the messages. Sending a reminder to a customer who has paid, or who is in a dispute, damages the relationship.
The agent stops and hands to a person when:
- a matching bank payment is found;
- the customer replies with a dispute, a query or a promise to pay on a date;
- the invoice is flagged on hold;
- the customer is flagged as sensitive;
- the contact on the invoice bounces.
A reply is read and sorted, in the same way as in the WhatsApp reply desk. A promise to pay moves the invoice to "promised" with a date, and the ladder resumes only if the date passes.
What does the agent never do?
- Send without approval. The message carries your name and affects a relationship.
- Change an invoice. No credit notes, write-offs or amended amounts.
- Offer a discount or a payment plan. Those are commercial decisions.
- Threaten. Legal action language is for a person and, where needed, a lawyer.
- Chase a disputed invoice. The ladder pauses until a person clears it.
These limits match the broader rule in approval placement for AI workflows: outbound messages and money wait for a named person.
How do you handle customers in different countries?
Terms, language and etiquette differ. A reminder tone that is routine in Singapore may be too blunt elsewhere. Language also matters: a customer in Indonesia may prefer Bahasa Indonesia, and one in Hong Kong may prefer Chinese. Build language and tone as settings per customer, and have the person who sends the message read the draft in that language.
Late-payment rules and interest provisions differ by country and by contract. We do not state any here. Check the contract and local law before adding interest or fees to a reminder.
What does the reviewer see?
A list ordered by amount and age. For each draft: the customer, invoice, amount, days overdue, previous reminders, and any recent reply. The reviewer sends, edits or holds. A batch of rung-1 reminders takes minutes to clear because they are routine. Rung-3 items take longer because they should.
Because the evidence sits beside the draft, the reviewer does not hunt through the ledger or the inbox.
How do you measure whether it works?
Keep it plain.
- Days sales outstanding or average days to pay, before and after. Take a baseline over a few months before you start.
- Share of invoices paid before rung 2.
- Number of chases sent to customers who had already paid. Aim for zero. Each case shows a gap in the stop conditions.
- Time spent on chasing per week.
We do not publish a result figure for our own ladder here. Record yours against your own baseline.
What does it cost to run?
The AI part is small. Our other narrow tasks cost between S$0.01 and S$0.06 each, such as about S$0.01 to sort a reply. A reminder draft is a similar size of task, so expect the model cost to be cents per draft. We have not published a measured figure for this agent, so treat that as an estimate. Hosting and the retainer are the larger lines.
Where KYN fits
This agent runs on KYN's own books alongside bills from Gmail and payroll on 2026 CPF rules. For clients we build it into the finance system in their own cloud account, with rungs, tone, stop conditions and approvers set to their terms.
Agents have their own restricted accounts. Every action is logged with the actor, and outbound messages, money, filings and deletions wait for a named person. The first 14 days are a review of your stack and interviews with your team. A full build ships in under 90 days. See finance and security.
Frequently asked questions
Should I chase at 3, 14 and 30 days?
Those are our settings, not a rule. Choose rungs from your payment terms and customer types. The structure of an early gentle note, a later direct one and a final escalation to a person travels well.
Will an automated reminder upset customers?
A reminder that arrives on time, with the right amount and a link, is usually welcome. The damage comes from reminders to customers who have paid or disputed. Stop conditions and a human approver prevent that.
Can the agent call the customer?
No. Rung 3 opens a task for the account owner to phone. A conversation about money is a person's job.
Checked 30 October 2026.
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