Use this skill when designing chart of accounts, automating reconciliation, managing AP/AR processes, or streamlining month-end close. Triggers on chart of accounts, bank reconciliation, accounts payable, accounts receivable, month-end close, journal entries, accruals, and any task requiring bookkeeping process design or automation.
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name
bookkeeping-automation
version
0.1.0
description
Use this skill when designing chart of accounts, automating reconciliation, managing AP/AR processes, or streamlining month-end close. Triggers on chart of accounts, bank reconciliation, accounts payable, accounts receivable, month-end close, journal entries, accruals, and any task requiring bookkeeping process design or automation.
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Bookkeeping Automation
Bookkeeping is the systematic recording and organizing of all financial transactions
for a business. Done well, it produces a reliable single source of truth for every
dollar in and out, enabling confident decision-making, clean audits, and accurate
tax filings. Automation shifts the work from data entry to exception handling -
the machine reconciles the routine, the human resolves the unusual.
This skill covers the design and automation of core bookkeeping workflows: chart of
accounts architecture, bank and credit card reconciliation, accounts payable and
receivable pipelines, month-end close checklists, recurring journal entries, and
expense management. It applies equally to spreadsheet-based setups, QuickBooks,
Xero, NetSuite, and custom-built finance tooling.
When to use this skill
Trigger this skill when the user:
Asks how to design or restructure a chart of accounts
Needs to automate or streamline bank reconciliation
Wants to build or improve an accounts payable (AP) workflow
Wants to build or improve an accounts receivable (AR) and collections process
Asks about month-end or year-end close procedures
Needs to create or automate recurring journal entries or accruals
Wants to implement an expense management and reimbursement system
Asks about the difference between accrual and cash basis accounting
Do NOT trigger this skill for:
Tax strategy, tax planning, or tax filing preparation (use a tax-specialist skill)
Financial modeling, forecasting, or FP&A (bookkeeping records history; FP&A projects forward)
Key principles
Double-entry is non-negotiable - Every transaction touches at least two accounts:
a debit and a credit of equal value. This self-balancing property is what makes
accounting auditable. Never design a system that records only one side.
Classify at the source - The cheapest time to categorize a transaction is
when it first enters the system. Reclassifying entries later is expensive and
error-prone. Design intake workflows (AP approval, expense submission, bank feed
rules) to capture the correct account, department, and project code upfront.
Reconciliation is the heartbeat - Reconcile bank and credit card accounts
at minimum monthly, ideally weekly. Unreconciled books drift from reality.
Reconciliation is what transforms a transaction log into trustworthy financials.
Separate duties - The person who approves a payment should not be the same
person who processes it. The person who records a journal entry should not be
the only person who reviews it. Segregation of duties prevents both fraud and
honest error.
Automate the routine, review the exception - Use bank feed rules, recurring
transaction templates, and scheduled journal entries for predictable items.
Reserve human attention for variance investigation, approval workflows, and
anything over a materiality threshold.
Core concepts
Double-entry bookkeeping
Every financial event is recorded as a pair of equal and opposite entries. Debits
increase asset and expense accounts; credits increase liability, equity, and revenue
accounts. The fundamental equation always holds:
The chart of accounts (COA) is the master list of every account used to classify
transactions. A well-structured COA uses a numeric scheme that groups by type:
Range
Type
Examples
1000-1999
Assets
Cash, AR, Inventory, Fixed Assets
2000-2999
Liabilities
AP, Credit Cards, Loans, Deferred Rev
3000-3999
Equity
Common Stock, Retained Earnings
4000-4999
Revenue
Product Sales, Service Revenue
5000-5999
Cost of Goods Sold
Direct Labor, Materials, Fulfillment
6000-6999
Operating Expenses
Payroll, Rent, Software, Marketing
7000-7999
Other Income/Expense
Interest Income, Gain/Loss on Sale
Keep the COA as flat as possible. Sub-accounts add granularity but also complexity.
Add a new account only when reporting genuinely requires it - not speculatively.
Accrual vs. cash basis
Dimension
Cash Basis
Accrual Basis
Revenue recorded
When cash is received
When earned (invoice sent or service done)
Expense recorded
When cash is paid
When incurred (bill received or work done)
Accuracy
Simpler, matches bank
More accurate picture of financial health
Required for
Small businesses, sole traders
Companies >$25M revenue (US GAAP), audit
Key accounts
No AR, no AP
AR, AP, accrued liabilities, prepaid
Most growing businesses should use accrual. Cash basis can mask real obligations
(e.g., a large unpaid bill not showing up as an expense yet).
Reconciliation
Reconciliation is the process of comparing two sets of records to ensure they agree.
Types:
Bank reconciliation - Match the general ledger cash account to the bank statement.
Identify timing differences (outstanding checks, deposits-in-transit) and errors.
Credit card reconciliation - Match the credit card GL account to the card statement.
AR aging reconciliation - Ensure the AR subledger total matches the AR control account.
AP aging reconciliation - Ensure the AP subledger total matches the AP control account.
Balance sheet reconciliation - Every BS account should have a schedule supporting
its balance (e.g., fixed asset roll-forward, prepaid amortization schedule).
Common tasks
Design a chart of accounts
Start with the standard numeric ranges above. Reserve gaps (e.g., 1100-1199 for
cash, 1200-1299 for AR) so related accounts cluster together.
Map every real transaction type to an account. If a transaction cannot be mapped,
add an account - but never use a catch-all "Miscellaneous" account for regular activity.
Create departments or classes at the reporting layer, not by multiplying accounts.
Use one 6100 - Payroll account with a department tag, not separate payroll accounts
per team.
Review quarterly: retire unused accounts, merge near-duplicates, add only what
reporting genuinely requires.
Automate bank reconciliation
Manual process baseline:
1. Export bank statement (CSV or OFX)
2. Import into accounting system or spreadsheet
3. Match each bank line to a GL entry by date, amount, and description
4. Flag unmatched items on either side
5. Investigate and resolve exceptions
6. Sign off when difference = 0
Automation levers:
Bank feed rules - In QuickBooks/Xero, create rules that auto-categorize
recurring transactions by payee name or description pattern (e.g., "STRIPE" -> Revenue).
Fuzzy matching scripts - For custom setups, match bank lines to GL entries
by amount tolerance and date window (±1 day, ±$0.01).
Auto-import OFX/CSV - Schedule a daily import so the feed is never more than
24 hours stale.
Exception queues - Surface only the unmatched items for human review. The
matched 90% should require zero human time.
Key reconciliation formula:
Bank Statement Ending Balance
+ Deposits in Transit
- Outstanding Checks
+/- Bank Errors
= Adjusted Bank Balance
GL Cash Balance
+/- GL Errors / Unrecorded Items
= Adjusted Book Balance
Adjusted Bank Balance must equal Adjusted Book Balance
Manage AP workflow
A clean AP process has five stages with clear owners:
Receive - Vendor sends invoice. Route to a single AP email inbox or portal.
Capture: vendor, amount, due date, PO number (if applicable).
Code - AP team assigns GL account, department/class, and project. Verify
against purchase order or contract if over approval threshold.
Approve - Require digital approval from budget owner. Use a materiality
ladder: e.g., <$500 AP auto-approves, $500-$5K requires manager, >$5K requires CFO.
Pay - Batch payments on a schedule (e.g., Tuesday/Thursday). Record the
payment in the GL on the date the funds leave. Use ACH over checks where possible.
Reconcile - Confirm paid invoices clear in AP aging. Reconcile AP subledger
to control account at month-end.
Automation targets:
Auto-extract invoice data with OCR (e.g., Dext, Hubdoc, AWS Textract)
Duplicate invoice detection by vendor + amount + date proximity
Auto-match invoices to purchase orders (3-way match: PO, receipt, invoice)
Scheduled payment runs with pre-built approval email workflows
Manage AR and collections
AR management is revenue already earned but not yet collected. Aging matters:
Age Bucket
Action
0-30 days
Standard - no action unless terms exceeded
31-60 days
Automated reminder email
61-90 days
Personal outreach from AR team
91-120 days
Escalate to account manager or leadership
120+ days
Consider write-off or collections agency
Automation targets:
Auto-generate and send invoices from billing system on trigger (usage, milestone, date)
Automated dunning sequence: email at net+1, net+7, net+14, net+30 overdue
Payment portal link in every invoice email (Stripe, PayPal, ACH direct)
Weekly AR aging report auto-emailed to finance and sales leadership
Auto-apply cash receipts to oldest open invoices (FIFO matching)
Month-end AR tasks:
Reconcile AR subledger total to GL control account
Review aging for bad debt candidates
Post allowance for doubtful accounts entry if needed
Streamline month-end close
See references/month-end-checklist.md for the full detailed checklist.
High-level close sequence:
Week 1 of close:
[ ] Lock prior-period transactions (prevent backdated entries)
[ ] Complete bank and credit card reconciliations
[ ] Reconcile AR and AP subledgers to control accounts
[ ] Process payroll journal entries
Week 2 of close:
[ ] Post depreciation and amortization entries
[ ] Post accruals (uninvoiced expenses, deferred revenue adjustments)
[ ] Post prepaid amortization
[ ] Reconcile intercompany accounts (if applicable)
Final close steps:
[ ] Review trial balance for anomalies
[ ] Tie revenue to billing system
[ ] Run flux analysis (month-over-month variance review)
[ ] CFO/Controller sign-off
[ ] Lock period in accounting system
[ ] Distribute financial package
Target a 5 business day close. Every day over 5 is a process failure worth investigating.
Automate recurring journal entries
Recurring entries are predictable in amount or calculation method. Automate them
with templates that post on a schedule:
Entry Type
Frequency
Calculation
Depreciation
Monthly
Asset cost / useful life months
Prepaid amortization
Monthly
Prepaid balance / remaining months
Accrued payroll
Monthly
Days worked but unpaid at period-end
Deferred revenue release
Monthly
Contract value / contract months
Interest accrual
Monthly
Outstanding loan balance * (rate / 12)
Template structure for any recurring JE:
Entry name: [Descriptive name - no abbreviations]
Debit account: [Account number and name]
Credit account:[Account number and name]
Amount method: [Fixed / Formula / % of balance]
Frequency: [Monthly / Quarterly / Annual]
Auto-reverse: [Yes for accruals / No for amortization]
Memo: [Period: {month} {year} - {description}]
Set accruals to auto-reverse on the first day of the next period. This prevents
the accrual from permanently inflating the expense balance when the actual invoice arrives.
Implement expense management
A clean expense process prevents both fraud and friction:
Policy first - Publish a clear expense policy: what's reimbursable, per-diems,
receipt thresholds, approval chains. No policy means no enforcement.
Capture at point of purchase - Employees photograph receipts immediately
(Expensify, Ramp, Brex). Never rely on paper receipts surviving a month.
Code on submission - Employee selects category and project. Finance reviews,
not re-enters.
Approval workflow - Manager approves via email or app before finance processes.
Sync to GL - Connect expense tool to accounting system. Entries post automatically
with correct account, department, and project coding.
Reimburse on schedule - Process reimbursements on a fixed weekly cadence.
Unpredictable reimbursement is a major employee satisfaction issue.
For company card programs:
Issue cards with individual spend limits and MCC (merchant category code) restrictions
Require receipt + memo within 48 hours of transaction
Auto-lock cards with outstanding unreconciled transactions over 30 days
Anti-patterns / common mistakes
Mistake
Why it's wrong
What to do instead
Using a single "Miscellaneous Expense" account for anything unusual
Makes financials unauditable; hides real spend patterns
Create the right account. If it recurs twice, it deserves its own account
Recording expenses on cash basis while using accrual for revenue
Produces misleading P&L - expenses are understated relative to the revenue they generated
Pick accrual or cash consistently and apply it to both sides
Reconciling only at year-end
Errors compound over 12 months; finding a $50K discrepancy in December is a crisis
Reconcile bank accounts monthly at minimum, AR/AP weekly
Letting AP aging grow unchecked
Late payments damage vendor relationships and can trigger supply disruptions
Review AP aging weekly; pay on agreed terms, not whenever
Auto-posting all bank feed transactions without review
Bank feed rules misfire; creates a false sense of reconciliation while errors accumulate
Review and approve bank feed matches before they post, or review exceptions daily
Not using auto-reversing entries for accruals
Accrual posts in Month 1; actual invoice also posts in Month 2; expense is double-counted
Always set accruals to auto-reverse on the first day of the following period
Gotchas
Bank feed rules that auto-post without review create silent errors - Bank feed rules in QuickBooks/Xero match by payee name or description pattern. When a vendor changes their billing descriptor, the rule stops matching and transactions land in an uncategorized account. Auto-approved rules mean this can accumulate for months. Review unmatched and newly categorized transactions daily.
Accruals without auto-reverse cause double-counting - If you post an accrued expense in Month 1 (e.g., $5K for uninvoiced consulting) and then the actual invoice also posts in Month 2, the expense appears twice. Always enable auto-reverse on accrual entries so they zero out on the first day of the next period before the actual invoice arrives.
AR aging report total not matching the GL control account signals a subledger problem - If the sum of all open invoices in the AR subledger doesn't match the AR balance on the general ledger, there's an unrecorded transaction, a manual journal entry that bypassed the subledger, or a data integrity issue. This must be resolved before month-end close, not ignored.
Cash basis and accrual basis entries mixed in the same period produce meaningless financials - Recording revenue when invoiced (accrual) but expenses when paid (cash) in the same reporting period makes the P&L unreadable and legally problematic. Pick one method and apply it consistently to both revenue and expense recognition.
A Miscellaneous Expense catch-all account that grows is an audit flag - Using a catch-all for transactions that don't fit neatly signals inadequate COA design. Auditors flag high-balance miscellaneous accounts immediately. Any transaction category that appears more than twice per quarter deserves its own account.
References
For detailed content on specific topics, read the relevant file from references/:
references/month-end-checklist.md - Step-by-step month-end close checklist with
task owners, timing, and sign-off requirements
Only load a references file if the current task requires deep detail on that topic.
Companion check
On first activation of this skill in a conversation: check which companion skills are installed by running ls ~/.claude/skills/ ~/.agent/skills/ ~/.agents/skills/ .claude/skills/ .agent/skills/ .agents/skills/ 2>/dev/null. Compare the results against the recommended_skills field in this file's frontmatter. For any that are missing, mention them once and offer to install:
