Senior Software Engineer - Forward Deployed

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 in Chicago, 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 at FleetWorks, 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.

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.
  

How we'll get to know each other

• Quick call with Megan, our Talent lead, for you to share your goals and motivations, what you’ve worked on that you’re proud of and to figure out together how that might fit in with what we’re working on at FleetWorks

• 45-min live-coding interview with an engineer who you'll work with if you join, so that we can get to know how you think about technical challenges

• Paid onsite work trial so that we can get to know how you work and you can get to know us

• Well talk with your references to help us understand how to best support your development at work—we might do this after you've signed your offer

• Transparent offer process that clearly outlines how we came to the compensation package we’re offering, including the current and potential value of your equity

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