Senior Product Engineer - AI

Department: Engineering

Location: Chicago

Employment Type: FullTime

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 Chicago office.
  

What we look for:

• 3–6+ years of professional software engineering experience, with clear ownership of complex, production-critical systems.
  

• Strong command of TypeScript, Node.js, and REST API design, including debugging and integrating with external systems.
  

• Hands-on experience with AI-driven systems, including tuning agent behavior, refining prompts, and shaping workflow logic based on customer feedback.
  

• Exceptional communication and judgment, especially when balancing speed, reliability, and real-world constraints.
  

• Based in Chicago with willingness to travel 20–30% to customer sites.
  

What We Offer:

• Top-tier cash + equity

• Medical, dental, and vision coverage

• Fully covered lunches and dinners

• High ownership environment with rapid growth

• The opportunity to shape the future of AI in freight