Adam Wingfield
5 min read
Let’s get this straight—adding a driver isn’t just about filling a seat. It’s about knowing exactly when your business can sustain it, when it needs it, and when waiting is the smarter move. Too many small carriers hire too early, chasing growth without the freight to back it up or the systems to support it. And what happens? Payroll gets tight. Equipment sits. Operations spiral. You’re not growing—you’re bleeding. Hiring has to be a strategic decision, not a hopeful one.
If you’re running a small operation and thinking about bringing someone on—whether it’s your first driver or your fifth—this article is your gut check. Because timing matters just as much as execution. We’re going to walk through the signs that it’s time to expand, the indicators that you’re not ready yet, and the foundational work you need in place before that hire ever sees the inside of your truck.
This is where most small carriers fall short. They land one good contract or start seeing some consistent freight on the board, and they think, “It’s time to scale.” But steady isn’t the same as sustainable. One broker with consistent loads is not a business model—it’s a dependency. And if that freight disappears, now you’ve got payroll due on a driver you can’t keep rolling.
Before you hire, ask yourself:
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Can I consistently cover an additional truck with profitable freight, not just movement?
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Do I have a backup plan if my primary source of loads dries up?
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Have I run the numbers beyond just the gross—factoring in fuel, payroll, insurance, and downtime?
If you can’t say yes to all three, you’re not ready. Waiting is smarter than hiring someone you can’t afford to pay three months from now.
Hiring a driver without knowing your cost per mile is like trying to win a race without knowing where the finish line is. You’ve got to know your breakeven down to the cent—per mile, per week, per truck.
If you don’t know:
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How many loaded miles you need to run weekly to stay profitable
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How much cash flow your business requires to cover payroll every two weeks
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How long you can float expenses if a shipper pays late or a load cancels
…then hiring isn’t a business decision—it’s a guess. And in this market, guesses get expensive real fast.
Here’s a better question than “Should I hire?” Ask: “Am I already maximizing the truck I have?” Too many owners jump to hiring because they’re tired. They want help. But the truth is, a second driver won’t solve a business that isn’t optimized. If your current truck isn’t running 5+ days a week, or if you’re turning down freight you could cover yourself, you’re not ready to hire—you’re ready to tighten up.
