Forward Deployed Engineer (Chicago)

FleetWorks is a vertical AI agent for the outdated freight brokerage industry. To book just a single truckload of Coca-Cola from Atlanta to Chicago, a freight broker has to send and receive up to 50 phone calls, emails, and text messages. This can take hours out of their day. FleetWorks automates this human labor with an omni-channel AI.

Our product is already used by many of the top 100 brokers in the U.S. This role is a good fit if you are excited to learn about logistics and are passionate about AI, owning product decisions, and great design.

Our AI solution is actively deployed with many of the top 100 freight brokers in the U.S. This Forward Deployment Engineer role is perfect if you thrive on bridging technology and customer success, enjoy being close to product deployments, and are excited about bringing cutting-edge AI directly to clients.

About you:

• You have 1+ years of engineering experience, ideally involving direct interaction with customers or on-site product deployments.

• You enjoy working closely with customers, gathering feedback, troubleshooting real-time issues, and directly influencing product improvements.

• You are based in Chicago or open to relocating.

• You want to make outsized impact and thrive when surrounded by top performers.

• You have a strong drive. Other people describe you as someone who takes their work seriously (maybe a little too seriously). It goes from just being a job to an obsession.

• You have to like challenges. This is hard. We handle tens of thousands of phone calls/emails per day and coordinate complex agentic workflows to make them happen. 

• You have to want to win.

Responsibilities:

• Deploy, integrate, and optimize FleetWorks solutions directly at client locations or remotely.

• Collaborate closely with clients to understand their unique operational needs, ensuring seamless integration and high customer satisfaction.

• Diagnose, troubleshoot, and resolve technical issues swiftly to maintain customer trust.

• Provide direct feedback to the engineering and product teams, advocating for enhancements based on field experiences.

• Continuously improve documentation, deployment practices, and client onboarding processes.

About the interview:

If we interview you, you can expect the following process

• A 30-min take-home technical challenge.

• Two 1-hour live coding interviews with engineers.

• A paid onsite work trial (number of days variable based on your availability).

• We may speak with 1–2 references that you provide.