Cowork Invoice Chaser Skill for Claude

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

• 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).
• 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.
• 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.
• 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
• 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