Senior Software Engineer - Forward Deployed
FleetWorksChicago, Illinois, United States • San Francisco, California, United States
Posted May 27, 2026
Full Time
About the Company
FleetWorks is a Y Combinator-backed startup specializing in automating the vast number of phone calls made annually by the freight industry. By streamlining these communications, FleetWorks aims to enhance efficiency and productivity for logistics companies. Their innovative solutions leverage advanced technology to deliver significant time and cost savings, setting them apart as leaders in their field.
Job Description
FleetWorks is building a modern, intelligent marketplace for freight booking. We're looking for a Senior Software Engineer to join our forward-deployed engineering team in Chicago, working directly with customers to understand their workflows and turn that knowledge into robust integrations and production features.
Requirements
- 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.
- 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.
- 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.
Benefits
- Top tier cash and equity compensation
- Competitive medical, dental, and vision benefits
- Fully covered lunches and dinners