FleetWorks Expands AI Freight Marketplace Following $17M Series A and SONAR Integration

In the U.S. freight sector, around 200,000 truckloads require broker coordination daily, with 80% still handled manually via phone calls, emails, and text messages. FleetWorks is automating those workflows by deploying AI agents that act as autonomous dispatchers and carrier sales representatives.

The San Francisco-based startup raised $17 million in funding, including a $15 million Series A led by First Round Capital with participation from Y Combinator, Saga Ventures, and LFX Venture Partners, according to TechCrunch. Alongside that capital, the company has scaled its operations to manage more than 30,000 daily loads across more than 40 freight brokerages, connecting with a network of over 29,000 vetted carrier motor carriers.

To make negotiations more responsive to fluctuating spot rates, FleetWorks integrated freight intelligence platform SONAR directly into its agentic workflows, FreightWaves reported in August 2026. The integration embeds live lane scores and TRAC rates across FleetWorks' voice, SMS, and email agents so brokers can quote against verified market benchmarks in real time.

Automating the Freight Desk

FleetWorks coordinates freight on two sides of the market. On the broker side, autonomous carrier representatives plug into transportation management systems (TMS) to analyze shipment requirements, evaluate carrier compliance, read warehouse appointment notes, and negotiate rates within preset guardrails. On the carrier side, an always-on dispatcher learns driver route preferences, equipment capabilities, and schedules to surface matching freight without forcing small fleets to scour load boards.

In a demonstration at FreightWaves' F3 event shared on YouTube, co-founder and CEO Paul Singer showcased how the system manages live inbound calls: the voice agent verifies the carrier's MC number, checks lane availability in the broker's TMS, reviews proprietary margin rules, and books the load into the customer's operational system without human intervention. The software also handles communications across email threads, drawing on warehouse knowledge bases to answer operational questions regarding appointment flexibility and facility hours.

According to reporting by FreightWaves, customers have seen a 30% increase in loads handled per person per day and a 1% to 4% gross margin expansion on covered shipments. The company has also solved complex telephony challenges, reporting a 96% success rate for AI agents navigating automated phone trees.

Founded by Logistics and Tech Operators

FleetWorks was founded in 2023 by Paul Singer and Quang Tran. Singer previously worked as a product manager at Uber Freight, where he led technical teams managing carrier quality and built dynamic carrier scorecards. Tran, who serves as Chief Technology Officer, previously worked on moonshot projects at Airbnb.

After OpenAI released its initial API tools, Singer and Tran traveled across the United States to spend time on brokerage floors and identify the operational bottlenecks slowing down freight desks, as reported in Yahoo Finance. They observed carrier sales reps spending entire mornings negotiating straightforward loads and handling high volumes of repetitive inquiries, leaving little time for complex problem-solving or route development.

Speaking on the FreightCaviar podcast, Singer highlighted that FleetWorks operates an in-person engineering culture in San Francisco and has expanded with an office in Chicago to remain close to the nation's freight brokerage hub.

Hiring Across Engineering, Deployments, and Product

To expand its platform, FleetWorks is hiring across its San Francisco headquarters and Chicago office. The company is seeking senior technical and deployment leaders who can handle rapid enterprise customer rollouts.

On the field operations side, the company is recruiting a Head of Solutions Engineering and a Head of Customer Deployments in San Francisco or Chicago. In both roles, the leaders personally run the company's most important implementations, write playbooks from their findings, and own customer deployments end to end from contract signature through onboarding, go-live, and steady-state adoption.

On the product development side, the team is hiring a Product Manager and a Senior Product Manager in San Francisco, offering $160,000 to $200,000. These hires partner directly with the CEO and founding team to refine product vision, strategy, and execution for marketplace products used by both carriers and brokers, collaborating across engineering, operations, and GTM teams.

Core engineering is expanding with a Senior Product Engineer in San Francisco and a Senior Software Engineer in San Francisco or Chicago, both offering $160,000 to $240,000. As early engineers, candidates own end-to-end feature development while working with TypeScript across the stack, interact directly with customers, and help shape the company's technical culture.

Open Roles at FleetWorks

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