# Paul Singer

> Paul Singer is the cofounder and CEO of FleetWorks, a San Francisco startup building always-on voice AI agents that handle the phone-and-email grind of freight brokerage. A former Uber Freight product manager and Yale economics grad, he started FleetWorks in late 2022 with cofounder Quang Tran, went through Y Combinator's Summer 2023 batch, and in October 2025 raised a $17M round (including a $15M Series A led by First Round Capital) to automate the matching of trucks with cargo across a $1T+ industry.

- **Role:** Cofounder & CEO at FleetWorks
- **Organizations:** FleetWorks, Uber Freight, L.E.K. Consulting, Point72 Asset Management, Yale University
- **Nationality:** American
- **Education:** B.A. in Economics, Yale University
- **Known for:** Cofounded FleetWorks and grew it from idea to a freight-automation platform serving thousands of carriers, Raised $17M including a $15M Series A led by First Round Capital, with Y Combinator, Saga Ventures and LFX Venture Partners participating, Onboarded 10,000+ carriers and dozens of brokers within the first six months

## Career timeline

- **2016** — Graduated from Yale University with a B.A. in Economics; also studied Chinese language and mechanical engineering
- **2016-2018** — Associate at L.E.K. Consulting; earlier roles included summer analyst work at Point72 Asset Management and Design for America
- **2018** — Joined Uber Freight as a Strategy & Planning Associate
- **2018-2022** — Held product management and strategy roles in carrier product at Uber Freight
- **2022** — Left Uber Freight in December to cofound FleetWorks with Quang Tran
- **2023** — FleetWorks goes through Y Combinator's Summer 2023 batch
- **2024** — Onboards 10,000+ carriers and dozens of brokers, including former employer Uber Freight, within six months
- **2025** — Raises $17M (incl. $15M Series A led by First Round Capital's Bill Trenchard); launches always-on AI dispatcher

## Achievements

- Cofounded FleetWorks and grew it from idea to a freight-automation platform serving thousands of carriers
- Raised $17M including a $15M Series A led by First Round Capital, with Y Combinator, Saga Ventures and LFX Venture Partners participating
- Onboarded 10,000+ carriers and dozens of brokers within the first six months
- Built and launched an 'always-on' AI dispatcher handling carrier and broker calls
- Graduate of Y Combinator's Summer 2023 batch

## Latest updates

- **2025-10** — FleetWorks raised $17M (incl. a $15M Series A led by First Round Capital) and launched an always-on AI dispatcher.
- **2025-02** — Appeared on The Freight Pod podcast (Ep. 56) discussing DeepSeek, lessons from Uber Freight, and FleetWorks' 10x ROI claims for brokers.

## Links

- Website: https://fleetworks.ai
- LinkedIn: https://www.linkedin.com/in/paul-singer/

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Profile page: https://yespress.io/paul-singer
Published by YesPress — https://yespress.io
Last updated: 2026-06-08