AI-driven logistics startup FleetWorks has raised $17 million to transform how small trucking companies connect with shippers, accelerating the movement of goods across the U.S.
The round includes a $15 million Series A led by First Round Capital’s Bill Trenchard — an early backer of Uber — with participation from Y Combinator, Saga Ventures, and LFX Venture Partners.
Founded by Paul Singer (former product manager at Uber Freight) and Quang Tran (former moonshot engineer at Airbnb), FleetWorks is building an AI-powered freight marketplace that automates the matching process between carriers and cargo. The platform already serves 10,000+ carriers and dozens of brokers, including Uber Freight, within just six months of launch.
“Freight has always been about relationships — endless calls, texts, and emails — but that’s inefficient,” said Singer, CEO of FleetWorks. “Our goal is to give small carriers the same technological advantage as the biggest logistics firms by automating all that coordination in real time.”
AI Dispatch for the Trucking World
FleetWorks’ system uses an “always-on” AI dispatcher, trained to understand how each carrier prefers to communicate — whether by text, phone, or through FleetWorks’ portal — and automatically match loads based on timing, location, pricing, and even personal preferences.
For example, the AI might recognize if a driver needs to return home by Friday or if a delivery site requires steel-toed boots, incorporating those factors into its matching logic.
“Freight is more fluid than people think,” Singer explained. “Pickup times, rates, and urgency can shift hour by hour. Our AI system ingests that live data from both sides and dynamically matches carriers to loads — often inserting them directly into a broker’s system.”
To minimize errors and “AI hallucinations,” FleetWorks uses multiple specialized models that handle distinct logistics tasks, with the dispatcher acting as a coordination layer pulling verified data from each.
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From Uber DNA to Freight Innovation
FleetWorks was born out of Y Combinator’s Summer 2023 batch and reflects lessons Singer learned during his time at Uber Freight: building technology is only half the battle — successful adoption requires change management.
“AI implementation isn’t just software,” said Singer. “It’s about helping people adapt — teaching teams how to use these tools and showing them the real business impact.”
That hands-on approach appealed to Bill Trenchard, whose previous investments include Flexport and Uber.
“Traditional software just doesn’t work for a system this complex,” said Trenchard. “FleetWorks’ AI fits naturally into how truckers and brokers already operate — it listens, learns, and interacts in real time instead of forcing new workflows.”
The Road Ahead
FleetWorks plans to use the new funding to expand hiring, scale its AI-driven marketplace, and grow its presence among small and mid-sized carrier fleets that form the backbone of U.S. trucking.
While other startups — like YC peer Oway and enterprise players such as Flexport and Uber Freight — are exploring AI in logistics, FleetWorks is zeroing in on the communication layer that powers freight matching itself.
“Our AI understands context — not just routes and rates,” said Tran. “It’s designed to make trucking faster, fairer, and more human, even as it becomes more automated.”
About FleetWorks
Founded in 2023, FleetWorks is a logistics technology company using AI to connect shippers and carriers faster and more efficiently. Its platform automates load matching, dispatch, and communication, helping small and mid-sized trucking fleets compete in an increasingly digital supply chain.
