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FleetWorksFleetWorksChicago, IL

Senior Software Engineer - Forward Deployed

Own end-to-end customer deployments of AI voice agents for freight logistics. Embed with operators in Chicago to build integrations, resolve live issues, and shape product roadmap based on real workflows.

Salary not listed
On-site3+ YOESolutions Architecture

About the role

What You’ll Do

  • Own customer deployments end-to-end, from initial scoping to integration design to production rollout
  • Work directly with customer operators and leaders to understand real workflows, pain points, and edge cases, translating them into clear, high-quality technical solutions
  • 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
  • Travel 20–30% to customer sites nationwide to unblock deployments, map operational processes, and ensure successful go-lives
  • Collaborate closely with product and core engineering to shape the roadmap based on what you observe directly on the ground
  • Develop tools and reusable workflows that improve deployment speed and reduce friction for future customers
  • Operate with extreme ownership, ensuring customers experience immediate and measurable value from our platform

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 and equity compensation—we aim to be above 75th %ile for companies who have raised a similar amount of cash
  • Competitive medical, dental, and vision benefits
  • Fully covered lunches and dinners
  • The opportunity to learn quickly, grow fast, and be rewarded for your contributions

Skills

TypeScriptNode.jsREST APIsAI AgentsPrompt EngineeringSystem IntegrationDebuggingProduction Systems
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