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FleetWorks raises $17M to match truckers with cargo quicker

October 14, 2025
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The 1000’s of small trucking firms that assist transfer items round america have a reasonably old-school means of doing issues, in line with Paul Singer. He would know — he left his product supervisor job at Uber Freight to start out an organization known as FleetWorks, which he believes will modernize issues.

Created throughout Y Combinator’s Summer season 2023 batch, FleetWorks has been creating a market that leverages synthetic intelligence to make quicker matches between provider firms and items that must be moved, releasing up extra time for staff on either side of the transaction.

Singer and co-founder Quang Tran, who labored on “moonshot initiatives” at Airbnb, suppose it’s a large alternative, and so they’ve discovered some critical buy-in: FleetWorks claims to have introduced greater than 10,000 carriers and dozens of brokers (together with Singer’s previous employer Uber Freight) onto its market within the first six months.

To push issues additional, FleetWorks has raised $17 million to place in the direction of hiring, business enlargement, and product growth, together with a newly-launched “always-on” AI dispatcher. The funding features a $15 million Collection A spherical led by First Spherical Capital’s Invoice Trenchard, who additionally led Uber’s seed spherical in 2010. Y Combinator, Saga Ventures, and LFX Enterprise Companions additionally participated within the Fleetworks Collection A.

“We in the end went with First Spherical Capital to steer the spherical as a result of, I imply, I feel they’re the preeminent investor in early stage investing,” Singer mentioned in an interview. “They had been one of many few who actually understood that we had been we had been constructing a market firm.”

Trenchard, who was additionally an early investor in Flexport, informed TechCrunch in an interview that he thinks AI is the easiest way to handle all of those transactions, particularly for small companies.

“Conventional software program is simply not good at this. You’re structuring information earlier than you even know precisely all the components that you must construction, and also you’re pushing folks by way of your cheese grater,” he mentioned. “That is clearly far more open-ended in the way in which you could have these conversations with folks and uncover what their actual pursuits are.”

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There are a variety of startups and established firms attempting to use AI to transport and logistics. Oway, one other YC-backed startup, is engaged on a form of Uber for freight, packing vans full that will in any other case be half-empty. Uber Freight can be getting its Fortune 500 clients to make use of a personalized LLM to type by way of all their information. Flexport, which offers extra with world transport, rolled out a set of AI instruments for its clients in February.

With FleetWorks, Singer and Tran have centered in on the communication that drives the trucking world. Singer mentioned he tries to know how every provider needs to speak and can give them a mixture of off-the-shelf and custom-developed voice and textual content fashions relying on what they want.

“Do they need a cellphone name? Do they need a textual content message? Do they wish to come to our portal and speak to an agent there?” he mentioned. From there, FleetWorks’ AI brokers assist match items with truckers, discovering out the place the truckers will likely be, when they are going to be there, and what value they should transfer the cargo, amongst different particulars. FleetWorks’ AI can even deal with extra nuanced however essential particulars, like: is the driving force heading to a facility that requires steel-toed boots? Or does the trucker must be house by Friday to be together with his household?

These are all issues that carriers and truckers already do within the present system. But it surely typically takes dozens (or extra) calls, texts, and emails to get this a part of the job performed, Singer mentioned. For small provider fleets, which make up the overwhelming majority of the business, that point is cash.

“We typically think about freight as this very inflexible factor, but it surely’s truly this very fluid system on either side. So for brokers, the pickup instances for the appointment is likely to be altering, or the worth is likely to be altering because the load turns into extra vital once we get nearer to the pickup time,” Singer mentioned. “So the information that these two sides are amassing sort of feed this AI-powered mind, and once we detect a match, we’re in a position to simply insert one of many carriers that makes use of FleetWorks instantly into the dealer’s system.”

That’s a whole lot of element and nuance for AI software program to deal with, so to chop down on hallucinations, Singer mentioned FleetWorks depends on quite a few fashions within the background that it has designed to be specialised round specific duties. The always-on dispatcher then pulls information from these discrete brokers.

But it surely’s not simply in regards to the tech — a lesson Singer says he realized from his time at Uber Freight. “[It’s] about serving to your clients by way of change administration, educating the group learn how to use it, and exhibiting them that there are alternatives for this to affect your small business,” he mentioned. “We’ve gotten actually good at AI implementation along with simply constructing the core brokers.”

That was a giant attractor for Trenchard as properly. “One of many issues we’ve been enthusiastic about with AI simply as a basic factor is it’s becoming into the behaviors that folks have already got,” he mentioned. “It’s not requiring you to vary the way you do enterprise.

Whereas there’s a whole lot of Uber DNA in what FleetWorks is constructing, Singer isn’t myopic. There’s a whole lot of younger software program expertise who wish to work on fixing issues within the bodily world, he mentioned. In truth, Singer joked he’s already employed some engineers who haven’t seen Shrek (2001).

“I by no means thought I’d really feel like an previous head,” he mentioned.



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