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 by building voice agents that transform the chaotic freight booking process into a modern, intelligent marketplace.
Requirements
- 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.
Responsibilities
- Own customer deployments end-to-end, from initial scoping to integration design to production rollout.
- Build production features and integrations that allow our AI agents to operate inside complex customer environments.
- Diagnose and resolve issues in the field, often in real time and with incomplete information, owning outcomes all the way through.
- Develop tools and reusable workflows that improve deployment speed and reduce friction for future customers.
- Work directly with customer operators and leaders to understand real workflows, pain points, and edge cases, translating them into clear, high-quality technical solutions.
- Collaborate closely with product and core engineering to shape the roadmap based on what you observe directly on the ground.
- Hands-on experience with AI-driven systems, including tuning agent behavior, refining prompts, and shaping workflow logic based on customer feedback.
Other
- Own outcomes end-to-end: diagnosing messy real-world problems, shaping technical solutions in the field, and ensuring our AI agents perform flawlessly in live operations.
- If you thrive in ambiguous environments, enjoy working directly with customers, and want to see your code deliver immediate operational impact, this role is uniquely high-leverage.
- Operate with extreme ownership, ensuring customers experience immediate and measurable value from our platform.
- Travel 20–30% to customer sites nationwide to unblock deployments, map operational processes, and ensure successful go-lives.
- Based in Chicago with willingness to travel 20–30% to customer sites.
