Lead Designer

FleetWorks is rebuilding the $1 trillion freight marketplace with AI. Every year, companies spend over a trillion dollars moving freight across the U.S. - but the system for matching trucks with jobs is still slow, manual, and fragmented. FleetWorks is fixing that.

We're turning today's chaotic freight market into a modern, intelligent marketplace - one where AI agents replace the endless phone calls, texts and emails and match jobs to trucks instantly.

As an early designer at FleetWorks, you will shape the way users interact with our AI-driven platform, directly influence product strategy, conduct user research, and play a pivotal role in crafting our company culture.

About you :

You have 3+ years of experience designing intuitive, user-centric interfaces for complex software products. We also consider exceptional candidates with strong portfolios demonstrating outstanding design thinking, including previous startup founders or individuals with unconventional paths.

Based in San Francisco or willing to relocate.

You're passionate and driven. Colleagues describe you as someone who deeply cares about your work, turning tasks into obsessions.

You thrive on tough challenges. Our product manages tens of thousands of interactions daily, and your designs will simplify complex AI-driven workflows.

You're competitive - you want to build the best possible product and design experiences users love.

Our values :

We build with speed : it's often better to launch and iterate than spend weeks agonizing over small decisions. Our team is oriented around quick iteration.

We build with empathy : logistics is an industry that can be frustrating and painful when things go wrong. We build for edge cases to solve the most challenging parts of managing freight.

No internal politics : Our team stays focused on core projects, so everyone at FleetWorks has significant autonomy to build. There are no micro-managers, low-value meetings, or jockeying for priority.

We skate to wear the puck is going : underlying AI technology is improving rapidly. We build products that take advantage of this wave.

About the interview :

We try to keep our process tight to respect candidate time :

A 30-minute interview with our design contractor.

A 30-minute interview with the CEO.

1-2 days paid onsite work trial (number of days variable based on your availability) including a portfolio presentation, white boarding session, and small live project in Figma.

What We Offer

Health plan

Unlimited PTO

Fully covered lunches and dinners.