FleetWorks has raised $17 million to grow its platform that matches cargo with trucking carriers, including a $15 million Series A led by First Round Capital, with participation from Y Combinator, Saga Ventures, and LFX Venture Partners.
The company will use the funds to expand its team, deepen broker integrations, and enhance its always-on dispatch engine. CEO Paul Singer, who left a product role at Uber Freight to start FleetWorks, said, “They were one of the few who really understood that we were building a marketplace company.”
Singer founded FleetWorks with Quang Tran, who previously worked at Airbnb. FleetWorks is addressing inefficiencies in freight logistics, where small carriers and brokers still rely heavily on phone calls, spreadsheets, and fragmented load boards. The platform connects carriers with cargo automatically, streamlines communications, and reduces delays.
“Live Dispatch” for Trucks — Not a Dashboard
FleetWorks operates as a continuous dispatcher, monitoring cargo requests and carrier availability in real time. Unlike traditional load boards, the system automatically handles routing, pricing, carrier preferences, and operational constraints, eliminating the need for manual input. Singer described the level of detail the dispatcher manages.
“Is the driver heading to a facility that requires steel-toed boots? Or does the trucker need to be home by Friday? Do they want a phone call? Do they want a text message? Do they want to come to our portal and talk to an agent there?” The dispatcher assigns each task to specialized models that work in parallel, ensuring accurate matching across multiple dimensions simultaneously.
The approach reduces repetitive back-and-forth communication. FleetWorks captures subtle operational requirements that typically require dozens of manual messages between brokers and carriers.
This automation helps smaller carriers access loads more efficiently while allowing brokers to focus on moving freight rather than coordinating logistics. The platform ensures that new loads are matched with the most suitable carriers immediately, increasing utilization and reducing idle time by running continuously in the background.
Why This Isn’t Just Another Freight App
FleetWorks differs from existing freight platforms such as Uber Freight, Flexport, and Convoy by embedding matching into the carrier’s preferred communication channels. The platform adapts to phone calls, texts, emails, and portal messages, enabling carriers to interact without changing their routines.
Bill Trenchard of First Round, who led Uber’s seed round, said, “Traditional software is just not good at this. You’re structuring data before you even know exactly all of the elements that you need to structure. You’re pushing people through your cheese grater.”
He added, “One of the things we’ve been excited about with AI just as a general thing is it’s fitting into the behaviors that people already have. It’s not requiring you to change how you do business.”
FleetWorks’ approach embeds automation in conversation rather than forcing carriers and brokers into rigid workflows. The system can handle nuanced requirements such as time-sensitive deliveries, load compatibility, and facility-specific rules while maintaining a consistent, real-time flow of updates.
