🎣 Freight’s $17M AI Dispatcher

October 14, 2025

We sat down with Paul Singer, Co-Founder & CEO at FleetWorks and former Product Manager at Uber Freight, at the company’s San Francisco HQ to talk about their newly launched AI dispatcher, the future of freight automation, and how brokers and carriers can adapt.

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FleetWorks Raises $17M to Build an AI Dispatcher That Never Sleeps

FleetWorks, a San Francisco–based AI startup transforming how freight brokers and carriers connect, has raised $17 million to launch its always-on dispatcher for the U.S. trucking industry.

“Covering a load in 2025 looks way too similar to covering a load in 1980,” Paul told us. “If you own a small trucking company, you’re spending over 10 hours a week just trying to fill a few trucks. We believe AI can make it more proactive.”

The company just announced a $17 million funding round led by First Round Capital to expand its always-on dispatcher for carriers and AI-powered carrier reps for brokers.

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

FleetWorks is already working with over 40 brokerages, including 15 of the top 100 in the U.S., helping them connect calls, texts, and emails into one intelligent platform.

🎧 Listen to our full conversation with Paul Singer on Spotify or YouTube.📰 Read the full story on FreightCaviar.com.

From left to right: Tom Stawinski, Bogdan Kruzhinskiy, Paul Singer, Paul Jaroslawski, and Krystian Gebis at FleetWorks HQ in San Francisco (July 2025).

This week's episode is brought to you by FreightFlex, GenLogs, and Shipper CRM.

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Carrier of the Week: Shiba Trucking

Shiba Trucking

  • MC: 1340388

  • Location: Alsip, IL

  • Years in Business: 3 1/2

  • Fleet Size: 34 trucks

  • Equipment: Dry van

  • Lanes: No specific lanes. Run everywhere if the money is right.

  • Phone number: (630) 240-8338 / shibatrucking.net

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