Nate Graham didn’t plan on a career in freight. He spent seven years at UPS, starting as a warehouse loader right out of high school and working his way up through part-time supervisor, driver, and eventually a full-time operations management role in Kalamazoo, Michigan. UPS even paid for his degree along the way. Things were going well, but in January 2023, he decided to make the jump to Fifth Wheel Freight. Three years in, he says it’s the best decision he’s made.
The misconception that almost held him back.
Coming from a transportation background, Nate expected freight sales to mean constant friction, like cold calls to people who didn’t want to hear from him, or carriers too busy or frustrated to engage. What he found instead surprised him: genuinely good people and relationships worth building, on both the customer and carrier side. A few difficult interactions don’t define the industry, even if they’re the ones that get talked about most.
The first win, and the first mistake.
Nate’s first customer came about three weeks into the job. It was a full truckload for a company that needed functional fitness equipment moved. That early win set the tone, and about ten months later he built out his own team. But the early days weren’t mistake-free. His biggest one, by his own account, was letting a problem sit instead of speaking up about it right away.
When a carrier canceled on him mid-day early in his career, his instinct was to quietly fix it before telling the customer. It didn’t work out, and he ended up having to explain a problem he’d already known about for hours. The lesson stuck with him:
"Communicate, no matter if it's good or bad, communicate it right away so you're on the same page."
What “uncapped commission” really means.
Freight sales was Nate’s first commission-based role, and the swings in pay took some adjusting to. His advice for anyone stepping into a similar structure is to know your monthly expenses well, so the ups and downs don’t catch you off guard. But he’s also clear about the upside. As a book of business grows, so does the ceiling on what’s possible. For Nate, that’s translated into buying a house with his wife and planning for a family, big milestones he credits to this career shift.
Is sales hard work, talent, or both?
When asked whether success in freight sales comes down to talent or work ethic, Nate landed on both. The volume matters! More calls made means more opportunities found, and there’s no way around simply putting in the time and the work. But knowing and learning the industry matters just as much. Brokers who can’t speak knowledgeably to customers and carriers don’t last long, no matter how hard they’re dialing.
Advice for someone starting tomorrow.
For a new grad walking into a freight sales role, Nate’s advice comes down to a few fundamentals:
- Get comfortable on the phone. A large share of the day is spent making calls, so comfort with that format matters early.
- Learn the systems. Being able to use the tools well and knowing the industry well is what turns effort into results.
- Don’t dwell on the no’s. Rejection is part of the job from day one, but the ability to brush it off and keep moving is what separates people who stick with it from those who don’t.
His broader pitch to anyone eyeing more traditional “desirable” sales paths, like tech or medical sales, without having considered freight: it’s a ride with real ups and downs, but the relationships built along the way and the ceiling on what’s possible make it worth a shot.
