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Senior Forward Deployed Software Engineer

FleetWorksChicago
On-site Full-time

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Experience Level

Senior

Qualifications

Responsibilities:Manage customer deployments from initial analysis to integration design and production rollout. Engage directly with customer operators and leaders to understand real workflows, pain points, and edge cases, and translate them into high-quality technical solutions. Develop production features and integrations that enable our AI agents to function effectively within complex customer environments. Diagnose and resolve field issues in real-time, taking ownership of outcomes throughout the process. Travel 20–30% to customer sites nationwide to facilitate deployments, map operational processes, and ensure successful go-lives. Collaborate closely with product and core engineering teams to influence the roadmap based on firsthand observations. Create tools and reusable workflows to enhance deployment speed and reduce friction for future clients. Demonstrate a strong sense of ownership, ensuring customers experience immediate and measurable value from our solutions.

About the job

Every year, companies invest over a trillion dollars in transporting freight across the U. S., yet the process for matching trucks with available jobs remains slow, manual, and fragmented. FleetWorks is revolutionizing this system.

We are developing advanced voice agents that transform the chaotic freight booking experience into a streamlined, intelligent marketplace. Our agents eliminate the need for endless phone calls, texts, and emails, efficiently connecting truckers seeking to earn money with loads requiring transportation.

As we expand our forward-deployed engineering team in Chicago, a crucial hub for our clients and the epicenter of U. S. freight operations, we seek a talented individual to embed directly into the environments where our product interacts with real users. You will collaborate closely with operators to gain firsthand insights into their workflows, translating that knowledge into robust integrations and production features.

As our inaugural Forward-deployed Engineer at FleetWorks, you will own the end-to-end outcomes: diagnosing complex real-world challenges, designing technical solutions in the field, and ensuring our AI agents operate flawlessly during live deployments. If you thrive in ambiguous environments, enjoy direct customer interaction, and are eager to witness your code deliver immediate operational impact, this position offers a uniquely high-leverage opportunity.

Learn more about our Series A funding here!

About FleetWorks

FleetWorks is dedicated to modernizing the freight transportation industry by leveraging cutting-edge technology to simplify and enhance the booking process, ultimately saving time and resources for companies across the nation.

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