Paul Singer says the thousands of small trucking companies that help move goods across the United States are doing things pretty old-fashioned. He would have known. He left his job as a product manager at Uber Freight to start a company called FleetWorks that he believes will modernize things.
Created during Y Combinator’s summer 2023 batch, FleetWorks has been developing a marketplace that leverages artificial intelligence to make faster matches between carriers and goods that need to be moved, freeing up more time for workers on both sides of the transaction.
Singer and co-founder Quang Tran, who worked on the Moonshot Project at Airbnb, said he saw this as a huge opportunity and received serious buy-in. FleetWorks claims to have introduced more than 10,000 carriers and dozens of brokers (including Mr. Singer’s former employer, Uber Freight) to its marketplace in its first six months.
To take things even further, FleetWorks has raised $17 million to fund hiring, commercial expansion, and product development, including its newly launched “always-on” AI dispatcher. The funding includes a $15 million Series A round led by Bill Trenchard of First Round Capital, who led Uber’s seed round in 2010. Y Combinator, Saga Ventures, and LFX Venture Partners also participated in FleetWorks Series A.
“We ultimately chose First Round Capital to lead the round because we think they are an outstanding investor in early-stage investing,” Singer said in an interview. “They were one of the few who truly understood that we were building a marketplace company.”
Trenchard, who is also an early investor in Flexport, told TechCrunch that he believes AI is the best way to manage all of these transactions, especially for small and medium-sized businesses.
“Traditional software is really bad at this, structuring data before you know exactly all the elements that need to be structured and forcing people through a cheese grater,” he said. “It’s definitely a much more freeing method in that you can have conversations with people and discover what their real interests are.”
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There are many startups and established companies looking to apply AI to transportation and logistics. Oway, another YC-backed startup, is working on something like an Uber for freight, filling trucks that would normally be half empty. Uber Freight also enables its Fortune 500 customers to use customized LLM to categorize all their data. Flexport, which handles more global transportation, rolled out a suite of AI tools to its customers in February.
Singer and Tran have used FleetWorks to focus on the communications that power the world of trucking. Singer said he is working to understand how each carrier wants to communicate and will offer a mix of off-the-shelf and custom-developed voice and text models as needed.
“Do you need a phone call? Do you want a text message? Do you want to come to our portal and talk to an agent there?” he said. From there, FleetWorks’ AI agents help match products with truckers, finding out details like where the trucker is, when they’ll arrive, and how much it costs to move the freight. FleetWorks’ AI can also handle more subtle but important details, such as: Is the driver heading to a facility that requires steel-toed boots, or does the truck driver need to be home by Friday to be with his family?
These are all things that truckers and truckers already do with their current systems. But completing this part of the job often requires dozens (or more) of phone calls, texts and emails, Singer said. For small airlines, which make up the vast majority of the industry, time is money.
“We sometimes imagine freight as something very rigid, but it’s actually a very fluid system for both parties, so for the broker, the promised pick-up time can change, or the price can change as the parcel becomes more important as the pick-up time approaches,” Singer said. “So the data that both parties are collecting is kind of feeding this AI-powered brain, so when it finds a match, it can insert one of the carriers using FleetWorks directly into the broker’s system.”
This involves too many details and nuances for AI software to handle, so to reduce hallucinations, FleetWorks relies on many models in the background designed to specialize in specific tasks, Singer said. An always-on dispatcher then retrieves data from those individual agents.
But it’s not just about technology. According to Singer, this is a lesson he learned from his time at Uber Freight. “[It’s] “It’s about helping customers through change management, teaching teams how to use it, and showing them that this has an opportunity to impact the business. We’re very good at not only building core agents, but also implementing AI,” he said.
That was a big attraction for Trenchard as well. “One of the things that we’re generally excited about about AI is that it fits into the behaviors that humans already have,” he said. “We don’t need to change the way we do business.
What FleetWorks is building has a lot of Uber DNA, but Singer isn’t short-sighted. There are a lot of young software talent who want to work on solving problems in the physical world, he said. In fact, Singer joked that he has already hired several engineers who haven’t seen “Shrek” (2001).
“I never thought I’d feel like an old head,” he said.
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