24 Claude Skills to Automate Your Invoicing

Prompt-based workflows that take the invoicing grind off your plate — drafting the invoice, chasing the late payer, matching the payment that just landed, and telling you in plain English who owes you what. Each one is a "skill": a structured prompt you hand to Claude with your data, and it does the job.

They're markdown. Add them to Claude as a Project, or paste them as prompts. Below are 24, grouped by the part of the cash-flow cycle they handle — and at the end, the faster path if you'd rather not paste prompts at all.

Get all of these as files: the whole set is free on GitHub → Claude Invoice Skills. Install it as a Claude Code plugin, or copy any prompt below.

What these are

A skill is a reusable prompt that does one job well. No code, no setup. Instead of writing the same "your invoice is overdue" email for the fifth time this month, or squinting at a bank statement trying to figure out which payment belongs to which invoice, you paste your data into a skill and Claude does it. You either paste it into Claude with your numbers, or save it inside a Claude Project so Claude keeps your business context and you reuse it in one click.

What it replaces: the manual half of invoicing software. The tool stores the invoice; you still chase, reconcile, categorize, and read the tea leaves. These skills do that part.

Setup: adding skills to Claude Projects

1. Open Claude (claude.ai or the desktop app) and create a Project.
2. Add your business context as project knowledge — your business name, payment terms (net 15? net 30?), your tone, your bank/currency, and the kinds of clients you bill.
3. Paste any skill below into the chat, add your data (the job details, a list of overdue invoices, last month's statement, a payout report), and run it.
4. Reuse it whenever the job comes up. The Project remembers your terms and tone so you don't re-explain them every time.

Setup: connecting live data (MCP)

For skills that need live account data — your Stripe payouts, your accounting ledger, your bank feed — an MCP connector lets Claude read directly from your tools instead of you exporting and pasting. It's optional and more technical to set up.

No MCP? Still works. Every skill below runs fine if you just paste the raw data — a CSV export, a screenshot of your invoice list, a copy of your bank statement.

The 6 most used

1. Generate an invoice from a job

Turns the details of a finished job into a clean, client-ready invoice.

Create an invoice for this job: [client name, work done, hours/quantities, rates]. My terms are [net 30, currency, tax rate]. Lay it out with line items, subtotal, tax, total, due date, and the next invoice number after [last number]. Keep the descriptions plain and professional.

2. Recurring invoice run

Generates the whole batch of monthly/retainer invoices in one go.

Here are my recurring clients and their monthly amounts: [paste list]. Generate this month's invoices for all of them — same line items as last month, dated [today], due [terms]. Number them sequentially starting at [number]. Flag any client whose amount changed so I can confirm before sending.

3. Escalating overdue reminder sequence

Writes the right reminder for exactly how late each invoice is.

Here are my overdue invoices with how many days late each one is: [paste]. For each, draft the right reminder. 1-7 days: light and friendly. 8-14 days: a firmer nudge. 15-30 days: direct, with consequences. 30+ days: a final notice before next steps. Include the amount, original due date, and a clear payment link or instruction in every one.

4. Match a payment to an invoice

Reconciles incoming money against open invoices so you stop guessing.

Here are the payments that hit my account this week: [paste amounts, dates, references]. Here are my open invoices: [paste]. Match each payment to an invoice. List the confident matches, the partial payments with remaining balances, and anything you can't match so I can chase it down.

5. Auto-categorize expenses

Turns a messy statement into clean, tax-ready expense categories.

Here's my card/bank statement for the month: [paste]. Categorize every line into standard buckets (software, travel, contractors, supplies, fees, etc.). Flag anything that looks personal, duplicated, or unusually large. Total each category and give me the grand total of business expenses.

6. AR aging report

Shows exactly who owes you what, sorted by how worried you should be.

Here are all my unpaid invoices with amounts and due dates: [paste]. Build an accounts-receivable aging report — group by current, 1-30 days, 31-60, 61-90, and 90+ days overdue. Total each bucket, total the whole thing, and tell me the three accounts I should chase first.

All 24 skills

Create & send invoices

1. Generate an invoice from a job — finished-job details → a clean, numbered invoice (see above).
2. Recurring invoice run — generate the whole monthly/retainer batch at once (see above).
3. Send-on-delivery invoice — draft the invoice and cover note the moment a milestone or delivery is done.
4. Line-item & tax builder — turn rough notes into proper line items, subtotal, tax, and the next sequential invoice number.

Payment reminders & collections

5. Pre-due nudge — a friendly "this invoice is due in 3 days" heads-up that prevents lateness.
6. Day-one overdue reminder — the gentle first nudge the day a payment slips past due.
7. Escalating reminder sequence — the right tone for 7 / 14 / 30 days late, in one batch (see above).
8. Final-notice drafter — a firm last warning before you pause work or hand it to collections.

Quotes, proposals & payment plans

9. Quote / estimate generator — a few bullets about the job → a client-ready quote with pricing.
10. Proposal drafter — a scope description → a structured proposal with deliverables, timeline, and price.
11. Quote-to-invoice converter — an accepted quote → the matching invoice, no re-typing.
12. Payment-plan builder — a fair installment schedule for a struggling client, plus the reminder for each installment.

Reconciliation & payment matching

13. Match a payment to an invoice — reconcile incoming money against open invoices (see above).
14. Partial-payment tracker — record a part-payment and calculate the remaining balance to chase.
15. Stripe / payout reconciliation — match a Stripe (or other) payout, minus fees, back to the invoices it covers.
16. Duplicate & unmatched-payment flag — catch double charges, mystery deposits, and payments with no matching invoice.

Expenses & categorization

17. Receipt-to-expense capture — a photo or text of a receipt → a clean expense line (vendor, amount, date, category).
18. Auto-categorize expenses — a statement → tax-ready categories with flags (see above).
19. Recurring-expense tracker — list every subscription and recurring charge, with the ones to cancel surfaced.
20. Billable-expense to invoice — pull client-billable costs out of your expenses and onto the right invoice.

AR aging, cash flow & disputes

21. AR aging report — who owes what, bucketed by 30 / 60 / 90 days (see above).
22. Weekly cash-flow summary — money in, money out, what's coming, and what to do about it, in plain English.
23. DSO & top-overdue digest — your days-sales-outstanding plus the customers dragging it up.
24. Late-payment dispute responder — a calm, fair reply to a client who's disputing or stalling on an invoice.

Every one of these is genuinely useful on its own. The catch is the same for all 24: you still have to remember to run them, paste the data, and send the output. Fine once a month at the kitchen table — less fine when invoices are going out daily and three payments just landed unmatched.

The faster path: let Ootto run them for you

The 24 skills above are free and they work. But they're still manual — you open Claude, paste the statement, copy the reminder into your email, mark the invoice paid yourself.

Ootto is the done-for-you version. Connect your tools once (Gmail, Stripe, and the rest), Ootto learns how your business bills and gets paid, and it runs these same jobs automatically — sending invoices, chasing overdue payments through every stage, matching incoming payments, categorizing expenses, and delivering your cash-flow and aging summaries — without you opening anything. It gets sharper every week as it learns which clients pay late and which reminders work.

The skills are manual mode. Ootto is autopilot. See what that runs at on the pricing page.

New to automating the back office? Start with our complete guide to AI business automation, or see the wider set in Claude skills to automate your small business.