FleetWorks Raises $17M for an AI Dispatcher That Never Sleeps

FleetWorks’ announcement positions the company as the go-to for brokers and carriers looking to cover loads faster.

“Covering a load in 2025 looks way too similar to covering a load in 1980,” said FleetWorks CEO Paul Singer. “If you own a small trucking company, you’re spending over 10 hours a week trying to fill a few trucks. That’s time that can be used to drive or spend time with family. On the broker side, you’re making over a hundred phone calls a day to cover a few loads. We believe AI can make it more proactive.”

Their new AI dispatcher works with thousands of carriers every day over phone, text, and email, to understand what they’re looking for, what equipment they have, and when they’re empty. Then it goes to work for the carrier, looking for loads that fit their parameters and getting them booked.

When we first interviewed Paul back in August of 2024, he told us:

“What we want to do with FleetWorks is create super carrier-sales reps — ultra reps. Pre-AI, a good rep could handle 20 or 30 loads a day. We already have reps handling over 75 loads per day, and we envision a world where an ultra rep does up to 200 loads per day with our product. This product and funding announcement bring us closer to that reality.”

Since that conversation less than one year ago, FleetWorks is now working with over 40 U.S. brokerages, including 15 of the top 100 U.S. brokerages, connecting their inbound calls, texts, and emails into one platform.

We sat down with Paul again in July, this time at FleetWorks’ HQ in San Francisco, to learn more about their new AI agent—the always-on dispatcher —and how Paul and FleetWorks see the industry evolving.

The always-on dispatcher gives FleetWorks’ broker customers access to prequalified carriers who may not be calling on their freight. Reps can continue to build the carrier relationship and address exceptions as they arise.

“Humans are super powerful in this process,” he told us. “They build relationships, solve messy edge cases, piece together ambiguous info. Tech should amplify that.”

Combined with FleetWorks’ existing always-on carrier rep, which is integrated into a broker’s TMS, FleetWorks makes brokers into superpowered versions of themselves.

On trust and safety, FleetWorks is pragmatic.

“AI can be a force multiplier on fraud prevention with things like voice verification, photo verification, and insurance management,” said Paul “We partner with great companies like Highway and Truckstop as an important baseline, and we think about many additional layers.”

The current AI agents are just the beginning of FleetWorks' vision of end-to-end booking automation, and they have the team to realize it.

Paul brings his building experience from Uber Freight, where he built the industry’s first real-time autonomous systems that manage carrier quality.

CTO Quang Tran previously worked on moonshot projects at Airbnb.

Bill Trenchard of First Round Capital is the lead investor for the just-announced $17 million funding round. Bill has a long track record of success, including being an early investor in companies including Uber and Flexport. 

Where is it heading from here? “

Brokers who get really good at using technology will continue to outperform,” Paul said. “We’re helping them get there faster.”

And he’s crystal clear on the role of humans.

“AI will not take your carrier sales job… Your job will look different,” Paul said. “Brokers will spend more time orchestrating technology and managing many AI agents working to make you more money.”