How FleetWorks' AI Dispatcher Is Revolutionizing Trucking with $17M Funding

Modernizing the Trucking Industry with AI

Thousands of small trucking companies in the United States still rely on outdated methods to move goods, according to Paul Singer. He left his product manager role at Uber Freight to co-found FleetWorks, aiming to bring modernization to this essential sector.

Developed during Y Combinator’s Summer 2023 batch, FleetWorks is building a marketplace that uses artificial intelligence to quickly match carriers with cargo. This innovation saves time for both sides of the transaction, making logistics more efficient.

Co-founders Singer and Quang Tran, who previously worked on ambitious projects at Airbnb, see a huge opportunity here. Their vision has gained significant traction: in just six months, FleetWorks has onboarded over 10,000 carriers and dozens of brokers, including Uber Freight.

Major Funding and Expansion Plans

To accelerate growth, FleetWorks has secured $17 million in funding. This includes a $15 million Series A round led by First Round Capital’s Bill Trenchard, who also backed Uber’s seed round in 2010. Other participants include Y Combinator, Saga Ventures, and LFX Venture Partners. The funds will support hiring, commercial expansion, and product development, such as the new "always-on" AI dispatcher.

Singer emphasized choosing First Round Capital for their deep understanding of marketplace companies. Trenchard believes AI is ideal for managing these transactions, especially for small businesses, as traditional software often falls short by forcing rigid data structures.

AI in Action: Communication and Matching

FleetWorks focuses on improving communication in trucking. By understanding each carrier’s preferred method—whether phone calls, text messages, or portal chats—the platform uses a mix of off-the-shelf and custom voice and text models. Its AI agents handle complex matching, considering factors like location, timing, pricing, and even specific requirements such as steel-toed boots or family commitments.

Currently, this process can involve dozens of calls and messages, costing small fleets valuable time and money. FleetWorks’ AI-powered system detects matches and seamlessly integrates carriers into brokers’ systems, adapting to fluid changes in pickup times or prices.

Tackling Nuances and Reducing Hallucinations

To manage the detail-rich environment and minimize AI errors, FleetWorks employs multiple specialized models for specific tasks. The always-on dispatcher aggregates data from these agents, ensuring accuracy. Singer highlights that success isn’t just about technology; it’s also about change management and helping customers adapt, a lesson from his Uber Freight days.

Trenchard notes that AI fits into existing behaviors without requiring business changes, making adoption smoother. Despite the Uber influence, Singer is open to diverse talent, noting interest from engineers eager to solve real-world problems—even if they haven’t seen classic films like "Shrek."