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FleetWorks is building voice agents and intelligent marketplace technology to modernize freight booking in the U.S. trucking industry, replacing manual phone calls and fragmented systems with AI-driven matching between truckers and loads.
You'll join the core engineering team as a Senior Backend Software Engineer deployed directly into customer environments. This is a high-leverage role combining hands-on software development with direct customer engagement. You'll own technical delivery for customer implementations and integrations, architecting workflows that encode real operational processes while integrating with messy, fragmented customer systems. You'll also develop core platform components and integration tooling that standardize patterns and help the team scale deployments efficiently.
Key responsibilities include leading projects from scoping through production rollout, navigating complex real-world constraints to design solutions that work in practice, providing field insights to shape product roadmap, and traveling 20–30% to customer locations.
You should have 3–6+ years of professional software engineering experience with clear ownership of complex, production-critical systems. Strong technical foundation required: TypeScript, Node.js, REST API design, and hands-on experience debugging and integrating with external systems. Experience with AI-driven systems is essential—tuning agent behavior, refining prompts, and shaping workflow logic based on customer feedback. Exceptional communication and judgment are critical, especially balancing speed, reliability, and real-world constraints. You must be based in Chicago with willingness to travel to customer sites.
FleetWorks recently closed a Series A funding round and offers top-tier compensation positioned above the 75th percentile for similarly-funded companies, competitive benefits (medical, dental, vision), fully covered meals, and the opportunity to grow quickly in a high-impact role where your code drives live operations within days.
