CFO & Advisory

Investor-ready financials: the data room checklist

Diligence does not fail on bad numbers. It stalls on numbers that cannot be reconciled to each other. The checklist is about making them agree.

A founder sends a deck with $1.2 million in annual recurring revenue. The investor's analyst opens the QuickBooks export and finds $940,000 of revenue for the year. Both numbers are defensible; nobody has written down how one becomes the other. Three weeks pass. That is the typical diligence delay, and it is a preparation problem, not a business problem.

Financial statements

  • Monthly profit and loss, balance sheet and cash flow for the last 24 to 36 months, on an accrual basis, from a reconciled file. Cash-basis books are the first thing an investor asks to be converted.
  • Annual statements for each full year, with the file locked at year-end so the numbers do not move under the reader.
  • A bridge from the management numbers to the tax return for each year, explaining the differences.
  • Bank statements for the last twelve months, and a reconciliation of closing cash to the balance sheet.

Revenue

  • Revenue by customer by month, in a single sheet that totals to the profit and loss. This is the sheet analysts spend the most time in.
  • For subscription businesses: MRR movements (new, expansion, contraction, churn) by month, with the definitions written down, and a reconciliation from MRR to recognised revenue to invoiced revenue to cash collected.
  • Deferred revenue schedule showing how prepayments unwind.
  • Customer concentration: top ten customers as a percentage of revenue.
  • Copies of the largest customer contracts and the standard terms.

Costs and headcount

  • Gross margin analysis with a written definition of what is in cost of sales.
  • Headcount list by role, start date, location, compensation and contractor versus employee status.
  • Payroll registers and the last four quarters of payroll tax filings.
  • Vendor list with annual spend over a threshold and copies of material contracts (hosting, leases, key suppliers).

Tax and compliance

  • Filed federal and state returns for every open year, with proof of filing and payment.
  • Sales tax registrations, nexus analysis and filed returns; a note on any state where exposure exists and has not been addressed. Unaddressed sales tax is the most common diligence finding for online businesses.
  • Form 5472 filings for foreign-owned entities; transfer pricing documentation where a foreign subsidiary or parent provides services.
  • 1099 filings, state annual reports, franchise tax confirmations, good standing certificates.
  • Any IRS or state correspondence, and how each item was resolved.

Capitalisation

  • Cap table, fully diluted, agreeing to the formation documents, stock ledger, SAFEs, notes and option grants.
  • Board consents and 409A valuations where options have been granted.
  • Debt schedule: lenders, balances, rates, covenants, security.

The model

A three-statement model that starts from the actuals in the data room and projects 24 to 36 months, with assumptions on a single sheet. The historical columns must equal the statements above to the dollar. Investors will rebuild the model; what they check is whether the founder's version was built from real numbers.

Format and hygiene

A folder structure that matches this list; PDFs for filed documents, spreadsheets for schedules, an index with dates; one named person answering questions within a day. Every number that appears in two places should agree, and where it cannot, a one-line explanation sits next to it.

Timeline

From reconciled books, two to three weeks to assemble. From books that have not been closed monthly, add the catch-up first. Starting three months before a raise is comfortable; starting after the term sheet is where founders lose leverage, because every week of diligence delay is a week the investor's enthusiasm cools.

The check: does the revenue figure in your deck reconcile to the accounting file in one written step? If not, that reconciliation is the first document to write.

Questions this raises

Do we need audited or reviewed statements?

Seed and Series A investors rarely require them; later rounds and acquirers often want a review or audit for the last one or two years. Reconciled, accrual-basis management accounts are the baseline at every stage.

Our books are cash basis. Is that a problem?

It is the most common conversion we do before a raise. Accrual statements for at least 24 months, with deferred revenue and accruals booked, are what investors expect.

Can you run the financial side of diligence?

Yes. As virtual CFO we assemble the financial data room, answer investor questions, and maintain the model through the process. Pre-raise engagements are quoted as a fixed project.

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