FleetWorks · 2 weeks ago
Senior Software Engineer - Forward Deployed
Chicago, IL
Full-time
Onsite
Mid, Senior Level
3+ years expFleetWorks is transforming the freight booking process with intelligent voice agents. As a Senior Software Engineer - Forward Deployed, you will work directly with customers to understand their workflows, develop robust integrations, and ensure the success of AI agents in real-world operations.
Transportation/Trucking/Railroad
Responsibilities
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
Qualification
Required
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
Benefits
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
Company
FleetWorks
Backed by Y Combinator Automating the 1B+ phone calls the freight industry makes every year
11-50 employees
H1B Sponsorship
FleetWorks has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2025 (1)
Funding
Current Stage
Early StageCompany data provided by crunchbase