Inside a Fourteen Month Catch Up Job for a Roofing Contractor

The Intake: What the Books Looked Like on Day One

The roofing contractor arrived with a stack of unopened bank statements, a QuickBooks Online file that had not been touched in over a year, and an email thread from a lender requesting financial statements within six weeks. The owner's personal credit card had been used for both business and family expenses. Payroll was run through a third-party service, but no payroll journal entries had been made in the books.

Nothing had been reconciled since the previous spring. Vendor invoices sat in email inboxes, and customer deposits were being collected through checks and a payment app. No one had tracked which deposits belonged to open jobs, which were retainage, or which were owner draws. The only digital records were bank exports in CSV format, but these had gaps where statements were missing.

The owner's goal was clear: clean books, a lender-ready P&L, and a balance sheet in just over a month. The firm's job was to estimate, price, and sequence the work so it could be delivered on time, while controlling the risk of surprises and ensuring the owner stayed engaged in the process.

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Scoping by Transaction Count Rather Than by Month

Catch up work for contractors rarely fits neatly into monthly packages. In this case, the transaction volume varied wildly from month to month. Storm season brought bursts of activity, while winter months were slow. Some months saw hundreds of deposits and expenses, others had only a dozen.

The initial review focused on total transaction count and the proportion that would require classification, documentation, or owner input. The firm exported all available bank and credit card data, ran a count for each account, and flagged any months with missing activity. This gave a realistic sense of the overall workload and avoided underestimating slow months where transactions were sparse but complex.

Estimating Owner Involvement

Many of the larger deposits were lump sums with no clear description. Vendor payments came from multiple sources and included personal card charges. The engagement would require significant back-and-forth with the owner to clarify transactions, provide missing invoices, and separate personal from business activity. The estimate included time for these requests and set expectations with the client from the start.

The Fixed Fee, the Deposit, and the Stop Work Clause

For this kind of engagement, hourly billing risked scope creep and payment delays. The firm proposed a fixed fee based on the transaction count and level of clean-up required. The proposal included a deposit up front, covering roughly one third of the total fee, and set milestone payments based on progress.

The contract spelled out what was, and was not, included. Only transactions within bank and credit card accounts would be classified and reconciled. Any research beyond basic categorization, such as chasing down missing statements or untangling owner loans, was clearly listed as an extra service.

Protecting the Firm: The Stop Work Clause

To control risk, the engagement letter included a stop work clause. If the owner failed to provide requested information after three nudges, work would pause until the required documents arrived. This clause protected the firm from endless follow-up and set clear expectations for the client. The owner understood that delays on their end would impact delivery to the lender.

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Rebuilding Feeds and Requesting Missing Bank Statements

With fourteen months of unreconciled activity, automated bank feeds had long since broken. The first step was to reconnect available accounts in QuickBooks Online and import as much data as possible. Where feeds were missing, the team manually downloaded statements from the bank's online portal.

Bank Portals and Missing Periods

Some smaller banks only allowed downloads for the past twelve months, leaving early months unavailable. The firm requested PDF statements directly from the owner, who in turn had to request archived documents from the bank. This process took several days, requiring follow-up calls and secure document uploads.

For one credit card used for both business and personal purchases, the firm had to download monthly activity and cross-check with the owner to identify which charges were deductible. This process highlighted the need to budget time for manual statement retrieval and owner involvement, especially in catch up jobs where feeds are broken and data gaps are common.

Job Costing After the Fact: Deposits, Retainage, and Materials

Roofing contractors often collect deposits up front and receive final payments after work is complete. In this case, the company held partial payments, retainage, and paid for materials out of pocket before reimbursement. None of this was tracked in the books.

Reconstructing Customer Deposits

The firm traced deposit records in the bank account, matched them to invoices and contracts provided by the owner, and built a schedule of jobs with outstanding and completed payments. Because deposit slips rarely listed job names, this required several rounds of clarification with the owner and sometimes with the office manager.

Retainage and Open Jobs

Retainage, where a portion of payment is held until job completion, complicated revenue recognition. The firm created a spreadsheet to track which deposits were retainage, which were final payments, and which belonged to jobs still in progress. This allowed for a more accurate balance sheet and profit and loss statement, satisfying lender requirements and giving the owner a clearer picture of cash flow.

Material Purchases Without Receipts

Material purchases were often made with the owner's personal card or with petty cash. Where receipts were missing, the firm worked with vendor statements and job logs to reconstruct costs. In some cases, they used delivery tickets or photos from job sites. This piecemeal approach was time consuming but necessary to allocate costs properly and ensure the books reflected true job profitability.

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Chasing Receipts on a Commingled Personal Card

One of the thorniest challenges was the owner's credit card, used for both business and family expenses. No separation existed in the statements, and few receipts were saved. To categorize these transactions, the firm set up a checklist of missing documents and sent weekly requests for receipts or explanations.

Owner and Team Communication

Some expenses, like meals and travel, required notes on the business purpose to qualify as deductions. The firm nudged the owner to forward receipts by photo or email. For recurring vendors, such as material suppliers, statements helped fill in gaps. Where documentation was missing and the owner could not recall the business purpose, the transaction was flagged as a personal draw.

The Role of Checklists and Status Updates

To keep the process moving, the firm maintained a status board showing all outstanding receipt requests, responses, and items pending owner review. This helped avoid duplicate requests and gave the owner a clear sense of progress. It also reduced confusion when multiple team members needed to follow up on different items.

Handoff to the Tax Preparer and the Move to Monthly Work

After six weeks of intensive communication, document gathering, and transaction coding, the books were reconciled through the end of the prior year. The firm generated lender-ready financial statements and delivered them to the tax preparer. All supporting documents were organized in a shared folder, with notes explaining any estimates or unresolved issues.

The catch up project revealed gaps in the contractor's processes, especially around expense documentation and job costing. The owner agreed to move to monthly bookkeeping, maintain separate cards for business expenses, and use digital receipt capture going forward. The firm set up recurring document requests and checklists to prevent backlog from building up again.

Catch up work for contractors tends to surface the same pain points: missing receipts, commingled accounts, and irregular transaction volume. Tools that automate client document requests, track checklist items by client, and display real-time status can make these jobs more manageable for both bookkeeper and client.