Invoice Chaser

Draft payment-reminder emails that get invoices paid without burning the relationship. The core judgment call is matching pressure to the situation: enough firmness to get paid, never more than the history justifies.

Step 1 — Gather the facts

Collect everything on this list before drafting. Never guess amounts or dates.

• Invoice number and amount
• Original due date → compute days overdue (today minus due date)
• Customer name and business
• Payment history: first-time customer / usually pays on time / chronically late
• Reminders already sent (how many, when, any response?)
• Any known dispute, hardship, or promise to pay
• How the customer can pay (payment link, check, card on file)
• Relationship value: is this a customer the user wants to keep?

If the user only says "they haven't paid," ask exactly two questions — "How many days overdue, and have you reminded them before?" — then draft with sensible assumptions stated at the top.

Step 2 — Pick the escalation stage

Then adjust for history:

• Good customer, first offense: soften one stage. A 25-days-overdue invoice from a five-year client gets Stage 2 tone, not Stage 3.
• Chronic late payer: harden one stage, and never re-send a friendly nudge they have already ignored.
• Ignored two or more reminders: move up one stage regardless of day count.
• Active dispute: stop escalating entirely. Address the dispute first (see Edge cases).

Step 3 — Write it

Rules that apply at every stage:

• Subject line = invoice number + amount + status. "Invoice #1042 ($1,850) — past due" beats "Following up!"
• Attach or link the invoice every single time. Never make them ask for it.
• One call to action: pay now, or reply with a payment date. Not both, not three.
• State days overdue as plain fact, without apology. No "sorry to bother you," no "just checking in."
• Keep it under 120 words through Stage 2; under 180 words after.
• Sign as the owner, from the owner's address. At small-business scale, email from "billing@" gets ignored.
• Never threaten anything the user will not actually do.

Full email templates for all four stages — plus dispute, broken-promise, and payment-plan variants — are in references/templates.md. Load that file before drafting.

Step 4 — Deliver

Output in this format:

**Stage:** 2 — Firm reminder (18 days overdue, usually pays on time)
**Subject:** Invoice #1042 ($1,850) — 18 days past due

[email body]

**If no reply by [date, 5 business days out]:** send Stage 3.
Want me to draft it now so it's ready?

Always include the "if no reply" line — chasing is a sequence, not a one-off. Offer to draft the next stage in advance.

Edge cases

• They dispute the work: do not send a reminder. Draft a reply that separates the disputed from the undisputed portion: "Happy to sort out [disputed item] — meanwhile the remaining $[amount] isn't in question. Can we get that settled this week?"
• They promised to pay and didn't: reference the promise with its date. This is Stage 3 regardless of day count: "On March 3 you said payment would go out that week."
• They claim hardship: offer a written payment plan with fixed dates and amounts, first payment small and immediate. $200 today beats $2,000 never.
• Small amount, long overdue (under ~$200, 60+ days): tell the user the truth — send one final demand, then weigh the cost of small claims or collections against writing it off and firing the customer.

What not to do

• Don't mention lawyers or collections before Stage 4 (or a genuine Stage 3 final notice).
• Don't stack apologies or soften with exclamation marks.
• Don't send reminders more often than every 5 business days.
• Don't re-send the same email twice — every touch either escalates or adds new information (a payment plan offer, a deadline, a consequence).

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