How do I automate invoicing and collections?

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Trigger the invoice off the event that ends the work rather than off someone remembering, then run a scheduled reminder sequence that escalates on its own and stops the moment payment lands. The hard part is not sending reminders, it is knowing reliably who has actually paid. That means the payment system and the invoicing record have to be connected. Most broken collections processes are broken there — a customer pays, nobody reconciles, and the automation keeps chasing them. Dunning a customer who paid last week does more damage than never reminding them at all, so the stop condition is the first thing to build, not the last: payment received, dispute opened, or a human flag on the account each have to halt the sequence immediately and across every channel. Define the trigger precisely, because 'work finished' is vaguer than it sounds. Is it the delivery confirmation, the signed acceptance, the shipment scan, the end of the service month? Whichever event you pick, it has to be recorded somewhere a system can see — which is why invoicing automation often starts by fixing how work completion gets captured. Invoices triggered off a reliable event go out the day the revenue is earned; invoices triggered off memory go out when someone catches up, and every day of that lag is a day added to your receivables. Treat each invoice as a record with a state — draft, sent, viewed, partially paid, paid, overdue, disputed — and let the reminder logic read the state instead of the calendar alone. That structure handles the real-world mess: partial payments that should shrink the chased amount rather than silence the sequence, disputes that must route to a person and pause everything, credit notes, and the customer with three invoices who pays the newest first. Sequences that only know 'sent' and 'paid' break on exactly these cases and teach the team to distrust the automation. Escalation should stay human at the end. Automate the first touches — a polite nudge before the due date, firmer notes after it, each one carrying the invoice, the amount, and a payment link so paying takes one click. But let a person handle the account that is genuinely in trouble; a payment-plan conversation, run by script, reads as a threat, and the relationship it burns is usually worth more than the invoice. The tone of the early reminders matters too: they should assume oversight, not delinquency, because that is almost always the truth. Once the pipeline runs, the reporting comes with it: days-sales-outstanding, who habitually pays late, which reminders actually move payments. Under Canadian rules, remember that even collection-adjacent messages are commercial electronic messages — CASL's identification and unsubscribe mechanics still apply to how the sequence is built.