Back
Who Will Run the Freight Operations of Tomorrow? Rethinking the Skills We Teach Today
Robert Nathan
My first executive title came at 16, from my dad, and it was a joke. He made me Vice President of Transportation at his fastener company, which meant hauling bolts all over Chicago that summer to pay for a car.
Then came the real education. I dispatched trucks on 2005-era software, and my best day ever was 48 loads. As a carrier rep at a top 50 brokerage, I bragged about how fast I could copy-paste between tabs, like that was a talent. Then I quit freight because I was sick of typing all day.
Twenty years later, I run Envoy, and our autonomous agent and execution layer, Ellie, does that typing. She books about 75% of the freight in our live accounts.
I’ll say it before somebody says it about me: I built the machine that does the job that made me, and I don’t know where the next me comes from. Whoever runs freight operations tomorrow has to learn to be the boss of machines, and freight isn’t teaching that.
So at my F3 fireside chat with SONAR’s Julie Van de Kamp on October 27, I announced Boss of Machines: AI Operations Lab. It’s a three-month internship and scholarship program that puts two college juniors or seniors inside Envoy in spring 2027 to learn how we build and run AI agents for freight.
It came out of a few general things I’d been dodging. What happens to the jobs that trained us? Are we preparing students for the industry they’ll inherit? Which skills will they need? And what do people like me owe them?
What Happens to Entry-Level Freight Jobs When AI Does the Grunt Work?
They dry up, and the classroom goes with them.
Stanford’s Digital Economy Lab found in August that employment for 22- to 25-year-olds in the most AI-exposed jobs had fallen about 19% behind same-age peers in less-exposed jobs, mostly because companies hired fewer of them. In a Gartner survey released in February, 55% of supply chain leaders expected agentic AI to shrink entry-level hiring.
My customers are part of this. Cooler Logistics told FreightWaves in July it scaled without adding headcount after deploying Ellie. I’m proud of that, and I’m not going to pretend it’s free.
The grunt work was the classroom. Typing receiver notes taught me which docks lie about their hours, and taking carrier calls taught me the difference between “I’m empty” and “I’ll be empty in an hour.” On one customer’s first load, Ellie took 76 carrier calls in five minutes. Every call lands in a Carrier Context Graph the brokerage owns. The kid who would’ve taken them never gets the lesson.
Are We Preparing Students for the Freight Industry They’ll Inherit?
No. We’re preparing them for my first job, and my first job no longer exists.
Don’t blame the schools. They teach what we hire for, and for 20 years freight hired for speed on the phones. We pulled kids out of a handful of Big Ten supply chain programs, handed them a headset, parked them next to our best rep for three months, and called it training. When the market turned, we walked them out.
Gartner found demand for supply chain roles requiring AI skills jumped 387% from early 2023 to early 2026, and most of those roles sit at the mid-senior level. So we’re all fighting over the same experienced people while we stop growing new ones.
You can’t promote a 2032 director you never hired in 2026.
What Did Learning Freight the Hard Way Teach Me?
Doing the work taught me freight. Being wrong in front of smarter people taught me how to run a company.
In 2008, in the middle of the Financial Crisis, I started LoadDelivered in Chicago, and we set up the phones ourselves. In 2012, I pitched our driver app to Jeff Silver, who was building Coyote. He asked how many loads we moved a day. Unless it was 10,000, he said, my app wouldn’t work. We did about 75. I sulked in my hotel room for a minute and killed the app that night.
Years later, Jon Gray, my camp counselor when I was 8 and now Blackstone’s president, gave my partner and me three hours. Our plan was basically “hire more people.” He told us there’s nothing special about adding bodies to grow bigger. I’d spent years paying people to touch freight and calling it moving freight well. I walked out of his office and never looked at a business the same way again.
How Do You Go From Doing the Work to Leading Digital Workers?
You trade your keyboard for judgment. Your job becomes deciding what the agents do, how much rope they get, when a human steps in, and who owns it when a load goes sideways.
I call that being the Boss of Machines, and Ellie runs that way. She shows her work, waits for approval, and earns more rope as your team trusts her, like any new hire.
In 2010, I told an interviewer that letting go and delegating didn’t come naturally to me. Frankly, it still doesn’t.
At one customer, after agents took over seven repetitive workflows, the reps asked for more automation. Their conversation went from: “What can AI do?” to: "What should I be doing next?” Those reps have a seat I never had. If my first job had looked like theirs, I’m not sure I’d have quit.
Which Skills Will Matter Most When AI Runs the Execution?
Judgment, problem-solving, technology fluency, and leadership, in that order. Typing speed is officially worthless.
Judgment: Making the calls that matter with context no system has. An operator overrode Ellie on a delivery appointment the TMS swore couldn’t move, and he was right: that receiver takes freight Friday or Saturday, first come, first served.
Problem-Solving: Asking why until you hit the real cause, so you stop patching. When the carrier who covered your Monday reefers all summer goes quiet, it might be the detention you never paid.
Technology Fluency: Thinking in workflows and feedback loops. You read what an agent did and why, tighten its rules when it drifts, and prove it’s making you money.
Leadership: Bossing a workforce that never sleeps without forgetting the one that does. My co-founder, Saumil Patel, says relationships get more valuable as AI runs more of the operation, and the carrier who only picks up for a familiar voice still needs one.
What Do Freight Leaders Owe the Next Generation?
A first rung. We’re the ones sawing through the old one, so we owe them a new one. And I’m the guy selling the saw, so I don’t get to wring my hands about it.
Economists Luis Garicano and Luis Rayo describe an old bargain in which “juniors paid for part of their training by doing the routine work.” That bargain is dying, and most of us are fine with it because it saves money this quarter. Robert Szczerba had the right fix in Forbes on October 19: whoever approves an automation has to name the manager responsible for the learning it kills.
Plenty of AI strategies in freight are a hiring freeze wearing a lanyard. If yours is to stop hiring juniors and poach seniors from the shop down the street, good luck. Everybody has that plan, and the shop down the street is reading this too.
So Where Does Boss of Machines: AI Operations Lab Come Into Play?
Boss of Machines: AI Operations Lab comes into play right where the old first rung used to be. It’s where I stop talking and start building.
I learned freight by typing. Our two students will learn those four skills by bossing the machines that do the typing, from deploying agents inside the systems customers already use to running a floor of people and agents. Each one who finishes earns a $2,500 scholarship toward fall 2027 studies.
We’ll name the two in January 2027. The application asks how technology can improve freight operations, so bring an opinion.
Two seats are a small start, but I’m a Cubs fan, so I know a good rebuild takes time.
What Should You Do Before You Sign Your 2027 Hiring Plan?
Email me before you sign it.
Find one entry-level seat in that plan and rebuild it as a seat that leads machines. Then hit me up directly at robby@tryenvoy.ai and tell me which one. I answer my own email.
If you teach supply chain, send me your sharpest juniors and seniors. If you run a brokerage and want your own version, I’ll give you everything we learn, mistakes included. And if you’d rather see Ellie work before you believe a word of this, book 30 minutes and we’ll run your ugliest lane live.
Somebody gave me three hours once. Who’s getting yours?
