Adam Wingfield

Tue, Jun 17, 2025, 2:29 PM4 min read

Everyone wants to scale. Until they do. That’s when the problems start.

Invoices get missed. Drivers start calling dispatch for payroll issues. You’re chasing paperwork, and no one can find the load confirmation for that Tuesday drop in Birmingham.

Adding trucks too fast without fixing your back office is like building a house on wet cardboard. It’ll hold for a little while. But the more weight you put on it, the faster it collapses.

This article breaks down what a back office actually is, why most small fleets ignore it, and how to build one that doesn’t fall apart when you scale from one truck to five and beyond.

The back office is everything behind the wheel:

• Billing and invoicing

• Driver settlements

• Dispatch and tracking

• Maintenance records

• Compliance (DOT, ELD, IFTA, insurance, etc.)

• Broker and customer communication

• Document management

If it’s not on the road and it keeps your business running, it’s back office.

Most carriers don’t think about it until it breaks. That’s too late.

Here’s what usually happens:

• 1 truck: You do everything yourself. Google Sheets, PDFs, and your phone.

• 2 trucks: You add a dispatcher or cousin to help, but no process.

• 3 trucks: Now there’s confusion over who’s doing what. Someone misses factoring paperwork. You’re getting calls from brokers.

• 4+ trucks: Dispatchers overlap, driver messages fall through the cracks, and customers start asking for updates you don’t have.

That’s not growth. That’s chaos. You didn’t scale your business. You multiplied your problems.

You need structure before trucks.

• One source of truth. TMS or shared spreadsheet.

• Every driver load, empty status, delivery time—clearly assigned.

• Avoid the “he said/she said” confusion with a documented system.

• Stop chasing PODs and rate cons in your texts.

• Use tools like Dropbox, Google Drive, or a document pipeline.

• Factoring? Set a weekly upload deadline. Monday cutoff. No exceptions.

• Weekly settlements should be automated, not guesstimated.

• Build a template: Gross revenue, deductions, fuel, escrow, pay.

• Consistency builds trust. One mistake, and a driver starts shopping.

• Keep a shared folder or app for all receipts, inspections, and PM logs.

• Miss one annual inspection, and your safety score takes a hit.

• Build a preventive calendar, not just a repair reaction.

• Who replies to what? What’s the update window?

• Use templated emails or check calls every X hours.

• Small fleets lose repeat freight because of weak communication. Fix it.