FleetWorks just closed a $17 million funding round to kill the phone tag that still dominates America's trucking industry.
The San Francisco startup raised a $15 million Series A led by First Round Capital's Bill Trenchard—the same investor who backed Uber's seed round back in 2010.
The company is betting that AI agents can replace the thousands of daily phone calls and email chains that freight brokers and carriers still use to book loads in 2025.
What FleetWorks Actually Does?
The trucking world moves 70% of America's freight, but 80% of those bookings still happen manually.
FleetWorks built an AI dispatcher that sits on top of existing broker systems and automates the entire dance—carrier outreach, price negotiation, and load coverage.
The AI adapts to how each carrier wants to work. Some prefer phone calls. Others like text messages. Some want to chat through a portal. FleetWorks handles all of it without forcing anyone to change their workflow.
FleetWorks Funding Breakdown
| Metric | Details |
|---|---|
| Total Raised | $17 Million |
| Series A | $15 Million |
| Lead Investor | First Round Capital (Bill Trenchard) |
| Other Investors | Y Combinator, Saga Ventures, LFX Venture Partners |
| Founded | 2023 |
| Announced | October 14, 2025 |
The Founders Behind the Platform
Paul Singer left his product manager role at Uber Freight to start FleetWorks with Quang Tran, an ex-Airbnb engineer who worked on moonshot projects.
Both founders come from deep logistics and tech backgrounds. Their first proof-of-concept was beautifully simple.
They posted a load on a board and watched three carriers negotiate directly with their AI agent.
Singer called that early version “janky” compared to what they've built since, but those three calls proved the concept worked.
The duo went through Y Combinator's Summer 2023 batch and haven't looked back.
Why This Round Matters?
Trenchard's involvement sends a clear signal. He previously backed Flexport and understands that AI thrives in environments with thousands of fragmented transactions across small operators.
The freight industry fits that profile perfectly. About 97% of carriers operate fewer than 20 trucks. That fragmentation creates massive inefficiencies that AI can solve at scale.
FleetWorks will use the capital for hiring, commercial expansion, and continued development of their always-on AI dispatcher technology.
Early Traction Numbers
The company onboarded over 10,000 carriers and dozens of brokers—including Singer's former employer Uber Freight—within just six months of operation.
That kind of two-sided marketplace liquidity is rare for early-stage logistics startups. It suggests strong product-market fit and validates that the market was ready for this solution.
Connect with FleetWorks
| Platform | Link |
|---|---|
| Website | fleetworks.ai |
| linkedin.com/company/fleetworks | |
| @fleetworksai | |
| Location | San Francisco, California |
The Road Ahead
FleetWorks now faces the challenge of scaling AI performance while maintaining accuracy across thousands of daily transactions.
Competition is heating up with players like Oway (another YC alum) and established platforms rolling out their own AI tools.
Success hinges on whether the AI can consistently reduce time-to-cover, increase tender acceptance rates, and deliver measurable ROI improvements in gross margin per load.
The $800 billion trucking market is massive, but execution will determine whether FleetWorks captures meaningful market share.
