According to Paul Singer, many of the thousands of small trucking businesses that transport goods across the U.S. still rely on rather traditional methods. Drawing on his experience as a former product manager at Uber Freight, Singer launched FleetWorks with the aim of bringing these operations into the modern era.
FleetWorks, which was founded during Y Combinator’s Summer 2023 program, is building a platform that uses artificial intelligence to quickly connect carriers with shipments, streamlining the process and saving time for everyone involved.
Singer and his co-founder Quang Tran, who previously worked on ambitious projects at Airbnb, see a significant opportunity in this space. FleetWorks reports that, within its first half-year, it has attracted over 10,000 carriers and several dozen brokers—including Uber Freight, Singer’s former employer—to its platform.
To accelerate their growth, FleetWorks has secured $17 million in funding to support hiring, business expansion, and product innovation, including the introduction of a new “always-on” AI dispatcher. The investment features a $15 million Series A round led by Bill Trenchard of First Round Capital, who also led Uber’s initial funding in 2010. Y Combinator, Saga Ventures, and LFX Venture Partners also joined the Series A round.
“We chose First Round Capital to lead this round because they are, in my opinion, the top early-stage investor,” Singer explained in an interview. “They were among the few who truly grasped that we’re building a marketplace business.”
Trenchard, an early backer of Flexport as well, told TechCrunch that he believes AI is the most effective way to manage these complex transactions, particularly for smaller companies.
“Conventional software just doesn’t handle this well. You’re forced to organize data before you even know all the variables you’ll need, and you end up forcing users through a rigid process,” he said. “AI, on the other hand, allows for much more flexible interactions, helping uncover what people actually want.”
Many startups and established firms are exploring how AI can improve logistics and shipping. Oway, another YC alum, is developing a freight platform similar to Uber, aiming to maximize truck loads that would otherwise be underutilized. Uber Freight is encouraging its large corporate clients to use a tailored LLM to analyze their data, while Flexport, which focuses on international shipping, introduced a suite of AI tools for its users earlier this year.
Singer and Tran have made communication within the trucking industry a central focus for FleetWorks. Singer explained that they tailor their approach to each carrier’s preferences, offering a combination of ready-made and custom voice and text solutions as needed.
“Do they prefer a phone call, a text, or would they rather use our online portal to chat with an agent?” he said. FleetWorks’ AI agents then help pair shipments with drivers, determining where and when truckers will be available, what rates they require, and other specifics. The AI can also manage more subtle but crucial factors, such as whether a facility requires steel-toed boots or if a driver needs to be home by the weekend.
All of these tasks are already part of the daily routine for carriers and drivers, but Singer pointed out that it often takes dozens of calls, texts, and emails to coordinate. For small fleets, which dominate the industry, that time translates directly to money.
“People often picture freight as a rigid process, but it’s actually highly dynamic on both sides. For example, brokers might change pickup times or adjust prices as deadlines approach,” Singer noted. “The information both parties gather feeds into our AI, and when a match is found, we can seamlessly integrate a FleetWorks carrier into the broker’s system.”
Managing this level of complexity is challenging for AI, so to minimize errors, Singer said FleetWorks uses several specialized models behind the scenes, each designed for specific tasks. The always-on dispatcher then draws on these models to operate efficiently.
But technology isn’t the only focus—Singer emphasized that his experience at Uber Freight taught him the importance of guiding customers through change, training teams, and demonstrating the business value of new tools. “We’ve become highly skilled at implementing AI, not just building the core technology,” he said.
This approach also appealed to Trenchard. “What excites us about AI is how it fits into people’s existing habits,” he said. “It doesn’t force you to overhaul your business processes.”
Although FleetWorks draws inspiration from Uber, Singer remains open-minded. He noted that many young software professionals are eager to tackle real-world challenges. In fact, Singer joked that he’s hired engineers who haven’t even seen Shrek (2001).
“I never expected to feel like the old guy,” he laughed.