Cowork Invoice Chaser

Chase receivables the way a firm-but-warm operator does: know exactly who owes what and for how long, escalate on a schedule, and never send a dunning email to someone who already paid. Inputs: a folder of issued invoices (PDF/.docx) and payment evidence (bank exports, remittance emails, a payments .csv, or a paid-list the user maintains).

Workflow

1. Build the ledger. Extract from every invoice: number, client, contact, issue date, due date, amount, terms. From payment records: date, amount, payer. Reconcile -- match payments to invoices (exact amount first, then partial payments, then aggregated payments covering multiple invoices).
2. Age the book. Produce the AR aging report: current, 1-30, 31-60, 61-90, 90+ days past due, by client. Include total outstanding, weighted average days late, and the three largest exposures.
3. Flag before chasing. List invoices with ambiguous payment status (partial matches, unidentified deposits near the amount) separately. These get a human decision, not a chaser.
4. Draft the chasers. For each confirmed-unpaid invoice, draft an email matched to its escalation stage -- drafts only, never send:
   • Due in 3 days: friendly heads-up with invoice attached reference
   • 1-14 late: polite nudge, assume oversight, restate amount and payment details
   • 15-45 late: direct, reference prior contact, ask for a payment date
   • 46-90 late: firm, propose a call, mention terms (late fees only if the invoice/contract actually states them)
   • 90+: final notice tone, next-steps language, flag to the human for a collections/legal decision
5. Digest. One summary per run: total outstanding and change since last run, payments received, drafts queued by stage, ambiguous items needing a decision, and clients whose pattern changed (reliable payer suddenly 30 days late is a relationship signal, not just an AR line).

Rules

• Never send -- drafts only. A wrong dunning email costs more than a late invoice.
• Never chase an ambiguous invoice. Unmatched payment evidence near the amount means human review first.
• Match tone to relationship: the user can tag clients (key account, standard, problem); key accounts never get form-letter tone regardless of age.
• One email per client per run, covering all their overdue invoices -- three separate nudges in one morning reads as automation and burns goodwill.
• State late fees only when the underlying invoice or contract specifies them. Never invent penalty terms.
• Keep the escalation memory: track what stage each invoice last received so a resent nudge escalates rather than repeats.

Scheduled Mode

As a weekly Cowork scheduled task: re-scan the folders, reconcile new payments, advance escalation stages, and deliver the digest with drafts ready for approval. The run is idempotent -- no invoice is double-chased within its stage window.

Quick Commands

• "Age my receivables" -- steps 1-2 only
• "Chase everything overdue" -- full workflow
• "Who pays late?" -- client payment-behavior profile from the ledger history
• "Draft the 90+ letters" -- final-notice drafts only