Senior Software Engineer

About this role

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 building voice agents that transform the chaotic freight booking process into a modern, intelligent marketplace. Our agents replace the endless phone calls, texts, and emails and match truckers who want to get paid with loads that need to be moved.

We’re expanding our engineering team in Chicago, a major hub for our customers and the heart of U.S. freight operations. In this role, you’ll be a full member of our core engineering team, but deployed directly into the environments where our product meets the real world. You’ll build production features, design integrations inside messy customer systems, and shape the internal tooling and platform components that allow us to scale deployments efficiently.


If you’re a strong software engineer who wants to work hands-on with users, solve ambiguous problems on the ground, and see your code driving live operations within days, this is a uniquely high-leverage role.

Learn about our Series A here!

## What You’ll Do:

• Lead technical delivery for customer implementations, integrations, and workflow builds; owning projects from scoping through production rollout.
• Architect and build workflows that encode real customer processes, integrating directly with their systems and adapting to operational edge cases you uncover in the field.
• Develop core platform components and integration tooling that standardize common patterns, reduce one-off work, and help the team scale customer deployments efficiently.
• Navigate complex environments, fragmented data, and real-world constraints, and design solutions that work in practice, not just on paper.
• Provide field insight to product and engineering, shaping the roadmap with firsthand customer understanding.
• Travel 20–30% to customer locations and work in-person from our Chi...