Executive Summary


  • Company Name: FleetWorks
  • Description: Fleetworks.ai provides an AI-powered "always-on dispatcher" for the trucking industry, automating load booking, carrier communication, and freight matching to save time and increase efficiency for both carriers and brokers.
  • Key Business Metrics:
    • 18 employees (up 125% YoY)
    • $17M in total funding
    • 24,600 monthly visits (+553.5% monthly change)
    • Onboarded over 10,000 carriers in the first six months and partnered with over 15 of the top 100 US freight brokers.
  • Primary Value Proposition: To reduce the manual communication overhead (phone calls, emails) in freight booking, allowing carriers to spend more time hauling and brokers to cover loads more efficiently.

Company Overview:


  • Business Model: B2B SaaS platform with a usage-based pricing model ($6 per load after a one-month free trial).
  • Target Market: The primary target markets are freight carriers (from owner-operators to large fleets) and freight brokers in the U.S. trucking industry.
  • Product/Service Portfolio:
    • Always-on Dispatcher for Carriers: An AI agent that finds and suggests high-paying loads matching a carrier's preferences, equipment, and availability.
    • Always-on Carrier Rep for Brokers: An AI agent that automates communication with carriers, including vetting, negotiating rates, and booking loads, integrating directly with the broker's TMS.
  • Geographic Presence: Primarily focused on the U.S. market, with headquarters in San Francisco, CA.

Leadership Team:


  • Founders & Key Executives:
    • Paul Singer (CEO & Co-Founder): Prior to Fleetworks, he was at Uber Freight, where he led the Carrier Quality Team. This experience directly informs the company's carrier-centric product philosophy. Holds an economics degree from Yale.
    • Quang Tran (CTO & Co-Founder): He was previously an engineer at Airbnb, where he worked on rebuilding the platform's architecture. Graduated from Carleton College with a degree in Computer Science.
  • Team Composition and Structure: The team is noted for its high concentration of technical talent, with a significant portion of the engineering team having prior experience as founders or CTOs.

Competitive Landscape:


  • Market Overview: The market for AI-powered automation in freight brokerage is nascent but rapidly growing, with several well-funded startups competing for market share.
  • Direct Competitors
    • HappyRobot: Another key player with a similar focus on AI communication for logistics, also recently funded, making them a direct and formidable competitor.
    • FreightStack AI: Their focus on "Workflow Intelligence for Logistics" aligns very closely with FleetWorks' mission to automate the communication and operational tasks for brokers and carriers. Both are tackling the inefficiencies in the back-office and communication loops
    • Loadsmart: While a larger and more established player, Loadsmart's use of AI to automate freight matching and booking puts them in direct competition. They are a prime example of the tech-driven evolution of freight brokerage that FleetWorks is also a part of.
  • Competitive Differentiation: Fleetworks' key differentiators appear to be its strong founding team with direct industry experience, its carrier-first approach, and its rapid product execution.

Market Fit & Dynamics:

  • Overall Assessment: Early, but Strong PMF.
    • Evidence:
      • High Adoption Rate: The rapid onboarding of carriers and brokers suggests the product is solving a significant and painful problem.
      • Customer ROI: Reports of customers seeing a 30% lift in loads per day and a 1-4% gross margin expansion provide strong quantitative evidence of value.
      • Founder-Market Fit: The founders' direct experience at Uber Freight and Airbnb provides them with deep insights into both the industry's problems and scalable technology solutions.
  • Areas for Development: While early signs are strong, achieving deep, lasting PMF will require moving beyond initial adoption to become an indispensable part of customers' daily workflows, as evidenced by high renewal rates and expansion revenue over time.
  • Market Positioning: Fleetworks is well-positioned as a potential category leader in the emerging AI-for-freight-brokerage space. Its carrier-centric messaging and dual-sided platform strategy are key differentiators.

Recent Developments & Insights:


  • Pre-seed: $500K from Y Combinator (September 2023)
  • Series A: $17M led by First Round Capital, with participation from Y Combinator, Saga Ventures, LFX Venture Partners (October 2025)

Key Insights

  • Product Launch (October 2025): Alongside the funding, the company officially launched its "always-on dispatcher" for carriers, expanding its product offering from a broker-centric tool to a two-sided marketplace.
  • Industry Recognition: Fleetworks was recently honored as a winner of FreightWaves’ inaugural AI Excellence in Supply Chain Award.
  • Substantial Funding: The recent $17M round provides a strong capital base to compete and scale.
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