Four brutal years. That’s how Dean Croke, Principal Analyst at DAT Freight & Analytics, describes the freight downturn the trucking industry just came through. Now he says the cycle is turning, and the turn itself might be the riskiest part.
Dean is a returning speaker at the 2026 MCIEF Leadership Conference in Scottsdale, where he’ll deliver a freight market update built on DAT’s data. Ahead of the event, he recorded a quick preview of what he’s watching right now, and why insurance professionals specifically need to be paying attention to freight data, not just loss ratios.
Why a Freight Data Analyst Talks to Insurance People
DAT sits on top of the largest freight network in North America, giving Dean a near real-time view into rates, capacity, and the balance of supply and demand across the industry. His argument for why that matters to insurance is pretty direct: coverage costs, claims, and safety records all live on the same profit and loss statement as freight rates and fuel.
“Understand where rates and margins are going, and you understand the financial health of the carriers you insure,” Dean said. “That is why freight data matters to your business.”
His bigger point is about timing. Freight data shows which segments are under financial pressure well before that pressure ever shows up in a loss ratio. Dean frames it as the difference between underwriting by looking in the rearview mirror versus underwriting by looking through the front windshield.
The Supply-Led Recovery Nobody’s Fully Trusting Yet
Dean says the biggest story in 2026 is a supply-led recovery, meaning the freight market’s upturn isn’t really being driven by demand yet. It’s being driven by capacity leaving the market, fast, and in a lot of cases, permanently.
“We’re tracking a structural drain on the driver pool from a wave of regulatory enforcement,” he said. “Spot rates are pushing record highs, even though they’re cooling a little bit now as we get past July 4th.”
That leaves an open question hanging over the whole industry: what happens when demand actually comes back, and there simply aren’t enough trucks on the road to move it? Dean also flags broker and carrier liability as something to watch closely, pointing to recent court decisions that are actively reshaping who ends up carrying the risk when a claim gets filed.
Why Leadership Matters Most at a Turning Point
Dean’s case for why a leadership-focused event matters right now comes down to timing more than anything else. The industry just came through one of the longest downturns on record, and now that the cycle is shifting, leaders have real decisions to make about capital and underwriting, decisions that need a clear read on where the market is actually headed, not where it’s been.
He also talked about what makes the Leadership Conference format different from just reading a market report. “MCIEF puts the current and rising leaders of this industry in one room to think through all of that together,” Dean said. He pointed to the Grand Hyatt Scottsdale itself as part of what makes that work, a relaxed setting where, as he put it, the real conversations happen over breakfast, on the golf course, and at the evening receptions.
“The best insight rarely comes from the stage alone,” he said. “It comes from the hallway and the dinner tables, and this venue is built for that.”
What He’s Actually Watching Right Now
Dean didn’t just tease his session, he gave a real preview of the data. He’s watching the structural change happening in the driver pool closely: a lot of the drivers being forced out of the industry through regulatory enforcement aren’t coming back, and the ones who do return are going to face more hoops to get their CDL license than before.
That single shift, he says, makes a real difference in how you underwrite fleets going forward. It’s exactly the kind of forward-looking detail that a static market report can’t capture the way a live freight market update can.
What This Means for You
If your work touches underwriting, claims, or carrier risk assessment in any way, Dean’s freight market update gives you something most quarterly reports can’t: a near real-time read on where rates, capacity, and carrier margins are actually headed, from someone sitting on top of the largest freight network in North America.
His full session in Scottsdale will build on everything previewed here, with a complete freight market update built on DAT’s data, timed specifically for this moment in the cycle.
Join Us in Scottsdale
The 2026 MCIEF Leadership Conference runs October 4 through 7 at the Grand Hyatt Scottsdale Resort. Along with Dean Croke’s freight market update, the agenda includes the MCIEF Top Trucking Insurance Industry Issues discussion, the State of the Market Report, and plenty of built-in time for the hallway and dinner-table conversations Dean says matter just as much as anything said from the stage.
As Dean put it: “After four hard years, this is a moment to get out ahead of the turn.” Register for the 2026 MCIEF Leadership Conference and reserve your seat in Scottsdale this October.
One more thing: the discounted hotel block at the Grand Hyatt Scottsdale Resort closes September 9, 2026. If Scottsdale is on your calendar this October, don’t wait on the room booking.
Not yet an MCIEF member? Membership gets you access to events like this one, along with the TRS and TCS designation programs and year-round continuing education built specifically for trucking insurance professionals. Visit mcief.org to learn more about membership and how to get involved.