Bookkeeping Copilot
Books that stay categorized and reconciled monthly without dread
The problem
Bookkeeping is the chore that slides. Transactions pile up for a quarter, then one grim Sunday gets sacrificed to categorizing them from memory ("what was that $84 charge in May?"). A generic AI prompt barely helps, because every chat starts from zero: it doesn't know your categories, your regular vendors, or that the same $210 supplier charge lands every month and is fine. So you re-explain, it re-guesses, and the books stay behind.
The tool
Once installed, this skill turns your AI assistant into a standing bookkeeper's assistant that already knows your chart of categories, your recurring vendors, and your month-end routine. Paste a bank or card export and get back every transaction categorized, the uncertain ones flagged for you instead of guessed, and anything odd called out by name.
The difference from a one-off prompt shows up in month two. Before: each session re-litigates whether "SQ *THE BEAN" is meals or supplies. After: the skill remembers your rulings, applies them consistently, and spends its attention on what changed: a duplicate charge, a subscription that crept from $49 to $79, a vendor it has never seen. It also runs your month-end close as a checklist, so "done" means the same thing every month. It is honest about its limits: it is not a licensed accountant or bookkeeper, and every close ends with a reminder to have your accountant verify anything that matters.
What's inside
- Transaction categorization from pasted exports, with uncertain items flagged, never silently guessed
- Anomaly flags: duplicates, price creep on regular vendors, charges that fit no known pattern
- A month-end close checklist sized to your business, with each step checked off in order
- Reconciliation help that compares your export totals to your books and narrows down mismatches
- Vendor memory: your categorization rulings stick, so every month gets faster
- A year-end handoff summary your accountant can work from without re-sorting everything
How to use it
- 1Click "Install skill" on this page and copy the install prompt.
- 2Paste it into your AI assistant (Claude, ChatGPT, Cursor. Anything that can fetch a URL or accept pasted text).
- 3Answer the skill's setup questions about your business and categories.
- 4Pick a monthly date and make it a ritual: export the month's transactions, strip out account numbers, paste them in, and work the close checklist top to bottom.
- 5When it flags an item as uncertain, rule on it once. That ruling is remembered.
Example
Say you run a two-van cleaning company. You paste 92 transactions from June. Output (condensed): "Categorized 86 of 92. Flagged for your ruling: $340 at a hardware store (supplies or equipment?), and two items I have no pattern for. Anomalies: the $89 charge from your scheduling software appears twice on June 12 and June 13, likely a duplicate worth disputing; fuel is up 22% on May with the same number of jobs. Month-end checklist: transactions categorized (done), receivables review (2 invoices past 30 days), HST set-aside check (pending your ruling on the flagged items). I'm not a licensed accountant or bookkeeper: please have your accountant verify anything important before you act on it."
Pro tip
In your first session, paste your accountant's category list or last year's expense categories instead of letting the skill invent its own. Books categorized the way your accountant already thinks save you a correction round at tax time, and the skill will hold that structure from then on.
Related tools
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