Ex-Uber Exec’s Startup Just Raised $17M to Revolutionize Trucking with AI — Here’s How It Works

FleetWorks Wants to Modernize How Truckers Get Matched With Cargo

Trucking is the backbone of America’s supply chain, but the way many small trucking companies operate today hasn’t changed much in decades. That’s exactly what former Uber Freight product manager Paul Singer set out to change when he launched FleetWorks — a startup on a mission to modernize freight logistics using artificial intelligence.

Created during Y Combinator’s Summer 2023 batch, FleetWorks is already making waves by building an AI-powered marketplace that helps match trucks with loads faster and more efficiently — and investors are taking notice.

$17 Million Raised to Supercharge Growth

FleetWorks has just secured $17 million in funding, including a $15 million Series A led by First Round Capital’s Bill Trenchard, who also backed Uber in its earliest days. Other investors include Y Combinator, Saga Ventures, and LFX Venture Partners.

This new capital will be used to:

• Expand FleetWorks’ team
• Grow its customer base
• Continue building its technology — especially its newly launched "always-on" AI dispatcher

Solving a Huge Problem for Small Trucking Companies

Across the U.S., there are thousands of small carrier companies that often rely on outdated systems — endless phone calls, texts, and emails — just to book jobs. It's time-consuming, inefficient, and often costly.

FleetWorks streamlines this process by using AI to:

• Understand what carriers need
• Match them with the right jobs
• Communicate via text, phone call, or through its online portal
• Handle details like delivery times, pricing, and even driver preferences

For example, if a trucker needs to be home by Friday or is headed to a warehouse that requires steel-toed boots, FleetWorks' AI takes that into account — all without the need for dozens of back-and-forth messages.

A Freight Marketplace Powered by AI

FleetWorks isn’t trying to replace human workers — it’s making their jobs easier. Its marketplace is designed to handle the messy, real-world complexity of freight logistics, using an AI engine that constantly learns and adapts.

So, how does it work?

• AI agents gather information from carriers and brokers
• The system figures out availability, pricing, delivery requirements, and more
• It then matches the right truck to the right load — instantly
• The match is pushed directly into the broker’s system, reducing manual effort on both sides

The platform has already onboarded over 10,000 carriers and dozens of brokers, including Uber Freight itself — where Singer previously worked.

What Makes FleetWorks Different?

FleetWorks isn’t the only company trying to bring AI to logistics, but Singer and his co-founder Quang Tran — a former engineer on “moonshot” projects at Airbnb — are taking a unique approach.

Instead of forcing users to change the way they operate, FleetWorks fits into the existing habits of truckers and logistics teams. That means:

• No need for new complicated software
• No forced workflows
• Just smarter, faster, AI-powered support behind the scenes

Singer said that the platform adapts to each user. If a driver prefers phone calls, the system can call. If they prefer text, it texts. It’s designed to communicate in a way that works best for the person behind the wheel.

Built for the Real World of Freight

Singer emphasizes that freight isn’t rigid — it’s fluid. Things change all the time: pickup windows shift, prices fluctuate, and drivers’ personal schedules matter.

That’s where FleetWorks' AI really shines. Its "always-on" dispatcher uses multiple specialized models working in the background, pulling real-time data and responding with flexible solutions.

This real-world awareness makes FleetWorks more than just a tech solution — it’s a freight-savvy AI assistant that understands the day-to-day reality of trucking.

Lessons from Uber Freight

Singer’s experience at Uber Freight played a big role in shaping FleetWorks. While Uber focused on automation and efficiency, he saw firsthand how important it is to help users manage change, not just force new tools on them.

That mindset now informs how FleetWorks helps customers adopt its platform — by focusing on training, support, and ease of use.

It’s not just about AI that works, it’s about AI that gets used.

Why Investors Are Excited

Bill Trenchard, the lead investor in FleetWorks’ Series A round, sees the company as a natural next step in logistics innovation. He believes that AI is the key to solving the complexity of freight, especially for small businesses that don’t have massive teams or tech budgets.

FleetWorks doesn’t try to control how carriers or brokers work — it supports them, quietly and effectively, in the background.

That approach, paired with strong early traction, made it a compelling bet for early-stage investors who are looking for the next big thing in logistics.

What’s Next for FleetWorks?

With fresh funding in the bank, FleetWorks plans to:

• Continue hiring top engineers and logistics experts
• Expand its customer base across the U.S.
• Refine and scale its AI models for even smarter matches
• Deepen integrations with broker systems

The ultimate goal? To become the go-to platform that connects small fleets and freight brokers in a smarter, faster, and more human way — all powered by AI.

Final Thoughts

FleetWorks isn’t just building another freight platform. It’s reimagining how the trucking industry communicates, connects, and operates — all with the help of artificial intelligence.

For the thousands of small trucking businesses that keep America’s supply chain moving, FleetWorks could mean fewer headaches, faster deals, and more time on the road — not on the phone.