FleetWorks is a freight-technology startup applying conversational AI to one of logistics' most labor-intensive problems: the constant phone calls, emails, and texts required to match available trucks with loads and keep shipments on track. The company was founded in 2023 by Paul Singer, a former product manager at Uber Freight who led teams responsible for carrier quality, and Quang Tran, an engineer with experience on moonshot projects at Airbnb. It was built during Y Combinator's 2023 cohort.
Freight brokerage and dispatch still run heavily on manual communication. Brokers and carriers spend hours each day calling around to cover loads, negotiate rates, confirm pickups, and run check calls on in-transit freight. FleetWorks automates this work with AI agents that proactively reach out to carriers, match trucks to available jobs, handle routine negotiation and booking steps, and provide status updates, freeing human teams to focus on exceptions and relationships rather than dialing.
The company describes its product as an always-on AI dispatcher, emphasizing that the agents operate around the clock and can handle the high call volume that human teams struggle to keep up with, particularly during off-hours. By automating outreach and load matching, FleetWorks aims to compress the time it takes to cover a load and to bring more transparency and speed to a notoriously fragmented market that moves hundreds of thousands of truckloads daily.
In October 2025, FleetWorks announced $17 million in new funding led by First Round Capital, with participation from Y Combinator, Saga Ventures, and LFX Venture Partners, launching its always-on dispatcher for the U.S. trucking industry. The raise reflects strong investor appetite for vertical voice and agent AI in freight, where margins are thin and operational efficiency directly drives profitability.
FleetWorks competes in a fast-growing FreightTech AI segment alongside other dispatch-automation startups, differentiating on its always-on agent model and its founders' direct operational experience inside Uber Freight's carrier operations.