A former Uber Freight product manager just closed a $17 million Series A to shake up America's $800 billion trucking industry. FleetWorks is using AI to instantly match cargo with carriers, cutting through the dozens of calls and emails that currently bog down small trucking companies. The kicker? The round was led by the same investor who backed Uber's seed round 15 years ago.
FleetWorks just proved that sometimes the best way to disrupt an industry is to understand it from the inside. Co-founder Paul Singer spent years watching Uber Freight try to modernize trucking logistics before deciding to build his own solution - one that speaks the language truckers actually use.
The startup's $17 million Series A, led by First Round Capital's Bill Trenchard, validates a simple but powerful thesis: America's thousands of small trucking companies don't need another rigid software platform. They need AI that adapts to how they already work.
"Traditional software is just not good at this," Trenchard told TechCrunch. "You're structuring data before you even know exactly all of the elements that you need to structure, and you're pushing people through your cheese grater." The investor, who led Uber's seed round in 2010, sees FleetWorks as the AI-native approach logistics has been waiting for.
The numbers back up that confidence. Since launching from Y Combinator's Summer 2023 batch, FleetWorks has pulled over 10,000 carriers and dozens of brokers - including Singer's former employer Uber Freight - onto its marketplace. That's serious traction in an industry known for being slow to adopt new technology.
But FleetWorks isn't trying to reinvent trucking communication. Instead, it's making the existing chaos work better. Singer's team built AI agents that handle the intricate dance of matching cargo with drivers across multiple channels - phone calls, text messages, portal conversations, whatever each carrier prefers.
"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?" Singer explained to TechCrunch. The AI then digs into the details that make or break actual deliveries: Will the driver be near the pickup location? Does the facility require steel-toed boots? Does the trucker need to be home by Friday for family time?
