Senior Software Engineer - Forward Deployed

FleetWorks is seeking a Senior Software Engineer for their Forward Deployed team in Chicago. This role involves embedding directly with customers to understand workflows, build robust integrations, and develop production features for AI agents that optimize freight booking. The engineer will own outcomes end-to-end, diagnosing real-world problems, shaping technical solutions, and ensuring flawless AI agent performance in live operations, contributing to a modern, intelligent marketplace for freight.

Must Have

• Own customer deployments end-to-end, from initial scoping to production rollout.
• Work directly with customer operators and leaders to understand workflows and translate them into technical solutions.
• Build production features and integrations for AI agents in complex customer environments.
• Diagnose and resolve issues in the field, often in real time.
• Travel 20–30% to customer sites nationwide.
• Collaborate with product and core engineering to shape the roadmap.
• Develop tools and reusable workflows to improve deployment speed.
• Operate with extreme ownership, ensuring measurable value from the platform.
• 3–6+ years of professional software engineering experience with complex, production-critical systems.
• Strong command of TypeScript, Node.js, and REST API design.
• Hands-on experience with AI-driven systems.
• Exceptional communication and judgment.
• Based in Chicago with willingness to travel 20–30% to customer sites.

Perks & Benefits

• Top-tier cash + equity
• Medical, dental, and vision coverage
• Fully covered lunches and dinners
• High ownership environment with rapid growth
• Opportunity to shape the future of AI in freight

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 forward-deployed engineering team, a major hub for our customers and the heart of U.S. freight operations. In this role, you’ll be embedded directly into the environments where our product meets real users. You’ll work side-by-side with operators, understand their workflows firsthand, and turn that knowledge into robust integrations and production features.

As our first Forward-deployed engineer, you’ll 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.

Learn about our Series A here!

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 + 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