Freight Tech Is Evolving—Here’s Why the Industry Faces More Scrutiny

Freight Tech Isn’t Dead – It’s Getting Picked Apart More Than Ever

Freight technology companies are still attracting investment, but the standards for earning that investment have become more demanding. Craig Dickman of TitletownTech discussed the changing market, startup failures and the qualities that matter most when evaluating logistics technology during an appearance on FreightWaves Today.

TitletownTech is an early-stage venture fund launched in 2019 through a partnership between the Green Bay Packers and Microsoft. The fund has raised more than $100 million and has made roughly 80 investments, with about 35 still active. Seven of those investments are focused on supply chain and mobility.

About 20% of the fund’s investments have failed. Dickman said the experience has changed what the fund looks for when it evaluates founders and their companies.

“My answer’s changed dramatically in the last five years,” Dickman said when discussing the leading causes of startup failure.

Market timing and weak product-market fit remain common problems. But in TitletownTech’s experience, conflict between co-founders has become an even more important warning sign. The fund now spends more time examining how founders communicate, handle disagreements and work through pressure.

“More often than not, the failures have come because the founders stop liking each other. Stop talking to each other,” Dickman said.

That lesson applies beyond venture-backed technology companies. Freight businesses regularly operate under pressure from fuel costs, equipment shortages, changing regulations, tight delivery windows and unpredictable demand. Technology may solve a specific operational problem, but it cannot compensate for a leadership team that cannot make decisions together.

TitletownTech invests from the pre-seed stage through Series A. That includes companies that may not yet have revenue or even a finished product. One of its notable supply chain investments is Genlogs, which the fund backed before the company had either.

The company’s founders opened their pitch with the line, “We used to track terrorists. Now we track trucks.” Dickman said the fund’s interest was not based on the phrase itself. Instead, TitletownTech was attracted to the founders’ unconventional approach and their idea of building a broad intelligence layer on top of freight data that can be incomplete or influenced by individual sources.

For truck drivers and carriers, data quality is a practical issue. Dispatch decisions, estimated arrival times, routing and equipment planning all depend on information that may come from multiple systems. If those systems do not accurately reflect what is happening on the road, the resulting technology can create more work instead of reducing it.

Another TitletownTech investment, the truck-platooning startup Peloton, demonstrated a different type of challenge. The company worked on digitally linking two trucks so they could operate more efficiently, with the goal of reducing fuel use and eventually increasing equipment utilization by allowing the driver of the trailing truck to go off duty.

According to Dickman, the technology itself was not the reason the company failed. A brake manufacturer declined to certify the brakes on the trailing truck. That decision prevented the company from obtaining insurance coverage, effectively stopping the operation from moving forward.

“They used a legitimate method to block the progress,” Dickman said.

The example shows how freight technology can be affected by established equipment, insurance and regulatory systems. A product may work in a technical demonstration, but adoption depends on whether carriers, manufacturers, insurers and regulators will accept it in real-world operations.

Dickman also said trucking backgrounds can produce strong technology founders because the industry demands rapid problem-solving and execution. He drew on his own experience running Paper Transport, which he grew from roughly 80 trucks to about 850 before exiting. About 90% of the company’s business is now in dedicated carriage.

“If you don’t innovate, you might die slowly, but if you don’t execute, you’re gonna die quickly,” he said.

That distinction is particularly relevant to drivers and fleets. New software or equipment may promise long-term efficiency, but it still has to work during a night dispatch, a missed appointment, a breakdown or a sudden change in a customer’s shipping plan. Freight technology earns its place when it supports those decisions without adding unnecessary complexity to the people doing the work.

Looking ahead, Dickman identified quantum computing as a potential opportunity for supply chain optimization. He pointed to routing problems, including versions of the traveling-salesman problem, as an area where the technology could eventually have an impact. He acknowledged that most people do not immediately connect quantum computing with freight, but said the transportation industry has a history of adopting difficult technologies early.

TitletownTech’s investment strategy is also shaped by its location in Green Bay, Wisconsin. The region sits near major Midwest freight flows and has access to truck, rail and Great Lakes harbor infrastructure. It also has a deep pool of transportation talent connected to carriers such as Schneider.

The fund operates near Lambeau Field under a structure tied to the Packers’ community ownership model. The team has 504,000 community shareholders, giving the organization a regional connection different from that of a privately owned professional sports franchise.

The broader message from Dickman’s comments is that freight technology investment has not stopped, but it is being evaluated more closely. Investors are looking beyond presentations and product concepts to examine founder relationships, execution, customer adoption and the industry systems that can determine whether a technology works at scale.