A bill gets paid, but the invoice supporting it never actually arrives — or it lands weeks later, after the entry's already been guessed at. This short course covers how to automate the chase without turning it into a monthly nagging exercise.
Key takeaways
A supplier delivers, you pay against a purchase order or a quoted amount, and the actual invoice either never arrives or shows up long after the payment's gone through. On its own that looks like a minor filing gap, but it delays proper coding, makes GST/HST input tax credit support incomplete, and leaves a payment sitting against nothing when your bookkeeper goes looking for it.
This lesson covers why the gap tends to be invisible until someone needs the paperwork — usually your bookkeeper preparing a period, or CRA asking for support on a claimed credit — by which point tracking it down takes far longer than catching it the week it was due.
Every expected invoice — tied to a purchase order, a recurring supplier relationship, or a payment already approved through a platform like Plooto — can be tracked against whether the actual invoice has been captured, usually through Dext or Hubdoc.
This lesson covers setting that tracking up against your real supplier list, so what gets flagged is a genuine gap, not routine noise from a supplier who always invoices on a different cycle than you'd expect.
When an invoice is overdue against what was expected, a follow-up email to the supplier — referencing the purchase order, delivery date and amount — gets drafted and queued, ready for a person to review, adjust and send rather than composed from scratch.
This lesson covers keeping that follow-up specific enough to get an actual response: naming the delivery and the amount rather than a generic request a busy supplier's accounts team can ignore for another week.
Choosing a supplier, agreeing terms, and deciding whether to release payment before an invoice arrives are all calls that stay entirely with whoever runs accounts payable. Automation handles the noticing and the first draft of the chase; it doesn't approve a supplier or authorize a payment.
By the end, the aim is a short, accurate list of the invoices that actually need a call this week — not a monthly scramble to reconstruct which of forty purchase orders never got billed.
A 30-minute call is enough to tell you whether AI pays for itself here.
