Bookkeeping for contractors and service businesses in MetroWest and Greater Boston.

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What documents do I need for catch-up bookkeeping?

Bank and credit card statements are the foundation. Every transaction that moved money in or out of your business appears on these statements, and reconciling them is how we verify your books match reality. You need statements for every business account covering the entire period that needs cleanup. If you have been behind for a year, that means twelve months of statements per account.

Most banks let you download statements going back several years through online banking. Even if you have not saved anything, you can usually retrieve what you need. Credit card companies work the same way. If you used personal cards for business expenses, pull those statements too so we can identify and categorize just the business transactions.

Prior tax returns help significantly. They show how income and expenses were categorized in previous years, giving us a template for consistency. If your catch-up bookkeeping spans tax years that were already filed, we need to understand what numbers were reported so the corrected books align with what you told the IRS.

Your existing QuickBooks file matters, even if it is a mess. Starting from a corrupted or incomplete file is often faster than rebuilding from scratch. If you gave up on bookkeeping six months ago but had clean books before that, we start from your last good close rather than recreating everything.

Invoices you sent to customers help when bank deposits do not clearly identify who paid you. A batch deposit showing “$8,400” without indicating which customers it came from creates guesswork. Your invoice records connect the dots.

Bills and vendor invoices add context to payments. A check to “ABC Supply” for $2,300 could be materials, equipment, or supplies. The invoice tells us what you actually bought. For contractors tracking job costs, these documents are especially important because we need to tie expenses back to specific projects.

Loan documents and statements are necessary if you have business financing. We need to track principal versus interest correctly, and your bank feed will not split those automatically.

Payroll records matter if you have employees. Pay stubs, quarterly 941 forms, and year-end W-2s. Payroll is often the trickiest part of catch-up work because taxes, withholdings, and employer contributions all need to tie out.

What if documents are missing? Most of it can be reconstructed. Banks provide statements going back years. The IRS can provide transcripts of filed returns. The harder gap is receipts and invoices you never saved. For those, local bookkeepers document what can be reasonably inferred and note any assumptions.

Gather what you have, and we can tell you what else we need once we see the scope. Perfect documentation makes the work faster, but imperfect documentation does not stop it.

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More Questions

Can a small business afford CFO services?

Yes, through fractional arrangements. A full-time CFO costs $150,000 to $300,000 annually. Fractional CFO services typically run $2,000 to $5,000 per month, making strategic financial leadership accessible for growing businesses.

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How do I manage cash flow as a contractor?

Construction cash flow is uniquely challenging because you pay for materials and labor before clients pay you. Managing it requires deposits upfront, progress billing, weekly AR tracking, and cash reserves for slow periods.

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How do slow-paying customers hurt my cash flow?

Late-paying customers force you to finance their work with your own money, creating a gap between when you pay expenses and when you collect. This leads to vendor relationship strain, credit card interest charges, lost discounts, and decisions made under pressure instead of strategy.

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What does catch-up bookkeeping cost?

Catch-up bookkeeping typically runs between $1,500 and $5,000 or more depending on how far behind you are, how many accounts need reconciling, and the state of your existing records.

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Can a fractional CFO help me get a business loan?

Yes, and this is one of the most valuable uses of a fractional CFO. They prepare the financial statements, cash flow projections, and documentation that banks require, and can present your business story in terms that lenders understand.

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What bookkeeping challenges do retail stores face?

Retail stores face unique challenges including high transaction volumes, inventory tracking, cash handling, multiple payment methods, and seasonal cash flow swings. Each creates opportunities for errors that compound quickly without proper systems in place.

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Full-service bookkeeping firm serving contractors and small businesses in MetroWest and Greater Boston. From monthly bookkeeping to job costing and payroll, we bring 20 years of hands-on business experience to your back office. Locally owned in Bellingham, Massachusetts.

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