Invoice Chaser.

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name: invoice-chaser
description: Drafts overdue-invoice reminder emails that escalate in firmness based on how many days overdue the invoice is and the customer's payment history. Use when the user wants to chase an unpaid invoice, follow up on a late payment, or send a payment reminder — trigger phrases include "hasn't paid", "invoice is overdue", "payment reminder", "chase this invoice", and "who owes me money".
---

# 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

| Days overdue | Stage | Posture |
|---|---|---|
| 1–7 | 1. Nudge | Friendly, assume oversight |
| 8–21 | 2. Firm reminder | Direct, ask for a payment date |
| 22–45 | 3. Final notice | Consequences named, deadline set |
| 46+ | 4. Demand | Last contact before collections or small claims |

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](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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