---
title: 'Product Manager at FleetWorks'
canonical: 'https://feeny.ai/job/product-manager-fleetworks-san-francisco-rgmhkvxj7303'
type: 'job'
last_seen: '2026-09-07'
---

# Product Manager at FleetWorks

- **Company:** FleetWorks
- **Location:** San Francisco, CA
- **Employment:** full-time
- **Work type:** onsite
- **Posted:** 2026-08-24
- **Last confirmed live:** 2026-09-07
- **Apply:** https://jobs.ashbyhq.com/fleetworks/d94af4c0-8b61-4421-831c-7b2c30cccd7d

## Job description

Every year, companies spend over a trillion dollars moving freight across the U.S - yet the system for matching trucks with jobs is still slow, manual, and fragmented. FleetWorks is fixing that.

We’re building omni-channel agents that turn the chaotic freight booking process into a modern, intelligent marketplace. Carriers and brokers, often small businesses and owner-operators, are the foundation of that system. Unlocking widespread adoption is one of the highest-leverage opportunities in the company and a core driver of our long-term trajectory.

We’re looking for a Product Manager who has owned and scaled products that became the industry standard, someone who knows what excellence looks like because they’ve built it. This is not an incremental role. You’ll partner with the CEO and founding team to refine the vision, strategy, and execution for our marketplace products for both carriers and brokers and 100s of thousands of AI powered interactions per day.

What you’ll do:

- Refine the vision, strategy, and roadmap for our broker AI product lines alongside the founders.
- Drive execution end to end, partnering closely with engineering, operations, and GTM to ship fast, iterate, and deliver measurable results.
- Set the bar for product excellence, establishing how we scope, prioritize, launch, and learn as we scale the product and the team.

What we look for:

- A product manager with a history of building high-impact, category-defining products.
- A 1→10 builder who thrives in ambiguity, scales products from first principles, and makes fast, high-judgment calls.
- Experience working with data in an AI-first environment. It’s more important to know the right questions to ask rather than writing syntax-perfect SQL
- Experience working with customers - scaling adoption and stewarding customers through change management
- A systems thinker with strong customer instincts, comfortable with both ground-truth insights and data.
- An owner with a founder’s mindset, operating close to the work and holding an exceptionally high bar.

## What we offer

- Top tier cash and equity compensation—we aim to be above 75th %ile for companies who have raised a similar amount of cash
- Competitive medical, dental, and vision benefits
- Fully covered lunches and dinners
- The opportunity to learn quickly, grow fast, and be rewarded for your contributions

## About FleetWorks

## Company Overview
- **One-liner**: FleetWorks uses AI agents to automate phone calls, emails, and negotiations between freight brokers and carriers, replacing manual load matching with an intelligent marketplace.
- **Entity Type**: Private (Series A)
- **Headquarters**: San Francisco, California, United States
- **Founded**: 2023
- **Founders**: Paul Singer and Quang Tran

## Core Business
- Primary industry/industries: Transportation, Logistics, Supply Chain, and Storage; Artificial Intelligence
- Target customers: B2B — Freight brokers, third-party logistics (3PL) firms, and carrier fleets (especially small to mid-size carriers)
- Mission or purpose statement: To rebuild the $1 trillion freight marketplace by turning a slow, manual, and fragmented system into a modern, intelligent marketplace where AI agents match jobs to trucks instantly.

## Products & Services
- **AI-Powered Freight Automation Platform**: A voice-first and email-capable AI assistant that automates the manual work of freight brokerage operations. The platform handles three core functions:
    - **Load Booking**: Automates outbound calls to carriers to share load details, negotiate rates, and book loads.
    - **Load Tracking**: Proactively calls drivers for status updates, detects live issues, and relays updates back to brokers.
    - **Appointment Scheduling**: Handles calls and emails to facilities to set or reschedule appointment times.
- **Always-On AI Dispatcher**: A recently launched feature that acts as a persistent, automated dispatcher, continuously working to match available trucks with loads without human intervention.

## Market Standing
- **Valuation/Market Cap**: Not disclosed
- **Key Metric: Total Funding**: $17.5M
- **Funding History**:
    - **Pre-Seed (Sep 2023)**: $500,000 led by Y Combinator
    - **Series A (Oct 2025)**: $17.0M led by First Round Capital (Bill Trenchard), with participation from Y Combinator, Saga Ventures, and LFX Venture Partners.
- **Notable Investors/Partners**: First Round Capital, Y Combinator, Saga Ventures, LFX Venture Partners. Key customer/adoption includes Uber Freight.
- **Growth Signals**:
    - Onboarded over 10,000 carriers and dozens of brokers within the first six months of 2025.
    - Headcount grew 115.4% year-over-year to 21 employees.
    - Actively hiring for 13+ open positions, primarily senior engineering and customer-facing roles.

## Competitive Advantages
- **SME Founder DNA**: Founder Paul Singer was a Product Manager at Uber Freight, giving the team deep, first-hand domain expertise in freight brokerage operations and the pain points of the industry.
- **Nuanced AI for a Complex Industry**: The platform uses specialized AI models designed to handle the complexity and nuance of freight, such as booking appointments, negotiating prices, and remembering driver preferences (e.g., facilities requiring steel-toed boots, desire to be home by Friday).
- **Focus on Change Management**: The company emphasizes not just building AI agents, but also helping large, established brokers implement the technology effectively, a key learning from the founder's time at Uber Freight.

## Strategic Focus
- **Commercial Expansion**: Using the $17M Series A to grow the sales and customer success teams to bring on more brokers and carriers.
- **Product Development**: Continuing to build and improve the "always-on" AI dispatcher and other core AI agents to increase automation rates and handle more complex edge cases.
- **Hiring**: Aggressively hiring senior engineering talent (Product Engineers, Forward Deployed Engineers) and senior customer-facing roles (Account Executives, Customer Success Managers) to scale the platform and support customer growth.

## Why Work Here
- **High-Impact Stage**: As a Y Combinator (S23) graduate with fresh Series A funding, the company is in a rapid growth phase, offering early employees significant ownership and influence over the product and culture.
- **Cutting-Edge AI in a Legacy Industry**: Employees get to work on applied AI problems (voice, text, multi-agent systems) that directly solve real-world problems in a massive, trillion-dollar market.
- **Founding Team**: The team is led by repeat founders with experience at top-tier tech companies (Uber Freight, Airbnb) and backed by elite investors (First Round Capital, YC).
- **Engineering Culture**: The active job postings heavily favor senior technical roles, suggesting a high bar for engineering talent and a focus on building a strong engineering culture.
- **Work Policy**: Positions are listed in San Francisco, CA, and Chicago, IL, with some roles likely being hybrid or in-office.
- **Compensation**: Senior engineering roles are listed with a salary range of $160K - $240K, indicating competitive compensation for the Bay Area.

## Sources
1. [fleetworks.ai](https://www.fleetworks.ai/)
2. [techcrunch.com](https://techcrunch.com/2025/10/14/fleetworks-raises-17m-to-match-truckers-with-cargo-faster/)
3. [ycombinator.com](https://www.ycombinator.com/companies/fleetworks)
4. [linkedin.com](https://www.linkedin.com/company/fleetworksai)
5. [jobs.ashbyhq.com](https://jobs.ashbyhq.com/FleetWorks)

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