Send invoice reminders

Send invoice reminders in Stripe — with the four heights of help laid out: do it now, make it easier for the next person to accept, work out the right move when you are stuck, and learn the pattern so it stops coming back.

4prompt heights
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The four heights

The same task, four distances: today's deadline, the next reviewer, the stuck moment, the pattern.

Execute — do the immediate task

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Send invoice reminders for all overdue accounts this Friday. Start with customers with balances…
Send invoice reminders for all overdue accounts this Friday. Start with customers with balances older than 30 days: Acme Co., Brightline LLC, and Echo Retail. Email finance@ourco.com a list of who will receive the reminders first, then send the reminders to customers in that order. Use a polite tone, state the outstanding amount, the original invoice date, and give a firm deadline of next Friday for payment or to request a short-term plan.

Improve — make it easier to accept

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Before sending overdue reminders, make them actionable for a busy payments contact. Put the exact…
Before sending overdue reminders, make them actionable for a busy payments contact. Put the exact amount due and a single big payment button at the top, list only the last three invoices with dates, and add a one-line note explaining late fees and how to request a payment plan. Highlight any account that previously asked for more time so we don’t retraumatize a contact or push them to dispute.

Decide — diagnose the stuck moment

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I scheduled reminder emails for Brightline LLC, but the CFO replied that aggressive reminders…

I queued reminders and the CFO warned about losing a customer

I scheduled reminder emails for Brightline LLC, but the CFO replied that aggressive reminders pushed them toward churn last quarter. I don’t know whether Brightline is late because of cashflow or because procurement blocks our vendor invoices. Which signals should I look for in the account history to decide whether to soften the language or escalate to an account manager, and what’s the fastest next step to avoid losing them while protecting collections?

Become — change the pattern

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We keep getting complaints from account managers that our overdue reminders trigger churn or…

Collections emails keep creating churn fights

We keep getting complaints from account managers that our overdue reminders trigger churn or disputes. Our finance team wants faster collection. What habitual change to our reminder cadence, language, or routing to account managers will reduce payment time without increasing customer churn?

Next to this one

Other payments work people do in Stripe.

Every task here came from the work, not from a feature list — which is why the prompts name what you want done and never the button that does it. The tool changes; the work does not.
Copyright © LLOS.ai · 2026 — original pedagogy, voice, and design — all rights reserved.

The rest of the map

Same library, five ways in.