FleetWorks has raised $17 million to speed up the way truckers and brokers match, betting that AI can compress the hours-long song and dance of calls, texts and emails that still characterize much of U.S. freight booking into minutes.
The round consists of a $15 million Series A led by First Round Capital’s Bill Trenchard, joining Y Combinator, Saga Ventures and LFX Venture Partners. The company says the money will be used to hire, grow its commercial presence, and continue building out its always-on AI dispatcher that automates carrier outreach, negotiation and load coverage.
Founded by former Uber Freight product manager Paul Singer and ex-Airbnb engineer Quang Tran, FleetWorks is a member of the Y Combinator Summer 2023 class. The company bills its marketplace as an AI-first layer that integrates on top of brokers’ systems and carrier communications, adjusting to how each would like to work — whether by phone, text, or portal chat.
Why Fast Matches Matter in the Trucking Industry
Freight is a huge but highly fragmented market. The American Trucking Associations says that trucks move more than 70 percent of the nation’s domestic freight in terms of weight — but about 97 percent of carriers own fewer than 20 trucks. That fragmentation breeds friction: brokers chase capacity among thousands of small fleets and carriers contend with moving appointment windows, commodity idiosyncrasies and fluctuating prices.
Deadhead miles compound the problem. DAT Freight & Analytics has long estimated that empty miles for long-haul carriers are close to 20% — a margin and emissions drag. If software can make matches tighter and predict where capacity will go faster, those miles disappear, utilization goes higher and loads get covered earlier — particularly in unpredictable lanes.
Regulatory guardrails heighten the stakes. ELD-monitored Hours-of-Service limits squeeze drivers’ available hours. Every additional phone call or appointment delay decreases compliance cushions and delivery windows. Faster, more accurate coordination isn’t simply about convenience; it underlies on-time performance and safety.
Inside FleetWorks’ Always-On AI Dispatcher
FleetWorks’ “always-on” dispatcher manages a collection of specialized AI agents. Instead of a one-size-fits-all model, the system funnels tasks — capacity outreach, requirements collection, setting of rates and updates on status — to bespoke models. That approach is intended to prevent mistakes, keep conversations based on verified data and create a record that brokers can audit.
Communication is the entry point. Some carriers prefer a phone call; some prefer text. Others opt for a portal. FleetWorks tailors itself to each, gathering operational information that normally requires dozens of back-and-forth messages: the truck’s location at a dock, equipment type, driver preferences and how flexible the appointment can be, as well as if any additional service beyond delivery is needed. It can also capture subtleties that sidetrack loads late — such as whether a facility is steel-toed boots required, if the driver needs to be home by Friday, or if a live unload can convert to drop-and-hook.
On the broker side, the network integrates with transportation management software, automatically injecting covered carriers into current workflows. The company is framing this not as a rip-and-replace system but as augmented brokerage: keep your processes, but let the AI cover loads and resolve paper trails behind the scenes.
Traction so far and the investor bet on FleetWorks
FleetWorks says it’s brought more than 10,000 carriers and dozens of brokers onto its platform in the first six months, with integrations at large brokerages like Uber Freight. Early as it is, that level of liquidity is essential for any freight marketplace; without that, even the smartest software stalls at its moment of truth — time to cover.
The investor syndicate represents a bet that the next generation of logistics software will be found in everyday conversations, not just spreadsheets and portals. Trenchard, who led Uber’s seed round years ago, is supporting the idea that AI agents can be dropped into existing processes and handle rote interactions without imposing an organization-wide workflow overhaul.
A crowded field, with room to run in freight AI
AI in freight is busy. Enterprise shippers, for their part, have been wooed by bespoke language models from Uber Freight. Rate discovery and shipment visibility AI tools were rolled out at Flexport. Another YC alumnus, Oway, is focusing on unused truck space as a way to reduce empty miles. The lesson of recent market cycles, as well as a series of high-profile fits and starts at digital brokerages, is that technology needs to be paired with deep operational know-how and change management in order to unlock durable margins.
FleetWorks differentiates itself by making AI native within the brokerage-carrier conversation, instead of creating another standalone board. If the dispatcher is able to consistently lower time-to-cover, increase tender acceptance and cut empty miles, the return on investment will be seen in gross margin per load — metrics by which brokers and carriers already measure themselves.
What comes next for FleetWorks and its AI platform
Look for the company to build more integrations with TMS providers, ELD/telematics platforms and facility appointment systems that will bring even more real-time data into the matching loop. That should make for better ETA accuracy, price discovery and exception handling when the inevitable weather, traffic, or dock delays hit.
The checklist for customers and investors is simple: measurable reductions in time-to-cover, fewer falloffs, better on-time performance… and lower deadhead. With most U.S. fleets still small and short of time, even incremental improvements on those metrics translate into meaningful dollars — and a quicker route from available truck to covered load.