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
Skills Required
- History of building high-impact, category-defining products
- Experience scaling products from 1 to 10 in ambiguous environments
- Experience working with data in an AI-first environment
- Experience working with customers, scaling adoption, and supporting change management
- Systems thinking and strong customer instincts
- Ability to make fast, high-judgment decisions and operate with ownership
What We Do
Backed by Y Combinator Automating the 1B+ phone calls the freight industry makes every year
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