How to automate payment reminders

Chasing money is the job nobody went self-employed for. You've done the work, sent the invoice, and now there's an awkward text to write — so it waits, and the invoice ages, and the awkwardness grows. Meanwhile most late payers haven't refused to pay at all; they've just forgotten.

Automatic payment reminders take the chasing off your plate. TradePlanr watches your unpaid invoices and sends a polite SMS nudge on a schedule you set — the same message every time, to every customer, with none of the Sunday-night dread. This tutorial covers turning them on, choosing the cadence, and knowing when to step in yourself.

1. 1. Turn on automatic payment reminders

   In Settings, open Reminders and switch on payment reminders. From then on, any invoice that passes its due date without being marked paid gets an automatic SMS chaser — you don't pick invoices one by one, and nothing slips through because you were busy.

   This is why marking invoices paid matters: TradePlanr only chases invoices it believes are outstanding, so keeping payments recorded keeps the reminders honest.

   The Reminders settings screen with the automatic payment reminders toggle switched on

2. 2. Choose your reminder cadence

   Set when reminders go out relative to the due date. A rhythm that works for most trades: a first nudge a few days after the due date, then a follow-up a week or so later if it's still unpaid. Frequent enough that the invoice stays on the customer's mind, spaced enough that it never feels like harassment.

   Resist the urge to chase on day one. A reminder that lands the morning after the due date reads as aggressive; one that arrives a few days later reads as organised.

   The payment reminder schedule showing a first reminder a few days after the due date and a follow-up after

3. 3. Get the tone right

   The first reminder should assume forgetfulness, not avoidance — a friendly note that the invoice is outstanding, with the amount and a way to pay. If your schedule includes a second reminder, it can be a touch firmer while staying civil: clear about the amount, clear that you'll follow up.

   Polite persistence collects far more than a stern letter. The customer who forgot feels gently prompted; the customer who was stalling realises the invoice isn't going to quietly disappear.

   Tip

   The automatic reminder has a quiet advantage over a personal text: it's obviously routine. “The system sent it” spares both sides the awkwardness, and keeps the relationship intact for the next job.

4. 4. Pair reminders with a payment link

   A reminder works best when paying takes less than a minute. With Stripe payment links switched on, every reminder carries a way to settle the invoice by card there and then — the customer reads the text, taps the link and pays before the kettle's boiled.

   Without a link, even a willing customer has to find your bank details and log into their banking app, and the moment passes. Reminder plus payment link is the combination that actually moves money.

   A payment reminder SMS on a customer's phone with the link to pay the invoice by card

5. 5. Know when to step in personally

   Automation handles the routine, but it shouldn't run forever. If an invoice has had two or three reminders and is heading past the month mark, that's the point to pick up the phone — there may be a genuine problem with the work, a dispute, or a customer in difficulty, and none of those are solved by a fourth text.

   Because every reminder is logged against the invoice, you go into that call knowing exactly what's been sent and when — and with a clean written trail if the debt ever needs to go further.

6. 6. Watch the overdue list shrink

   Keep an eye on the Overdue filter in your invoices over the next few weeks. Most trades find the same pattern: the forgetful majority pay off the first reminder, a few need the second, and the list of invoices that actually need a personal chase gets short enough to handle in one cup of tea.

Set the cadence once and the chasing runs itself: polite, consistent and never forgotten because you had a busy week. You stay the reasonable tradesperson who did good work — the reminders do the nagging.