Senior Backend Engineer: AI-Driven Freight Ops

FleetWorks Technology; Chicago (IL); On-site; USD 120,000 - 180,000; Full time

Benefits offered by this job

Top-tier compensation and equity

Medical, dental, and vision benefits

Fully covered lunches and dinners

Growth opportunities and quick career-

Job summary

FleetWorks Technology is expanding its Chicago-based engineering team to deliver production-grade software that connects truckers with loads. You will own customer implementations, design workflows, and build scalable platform components while traveling 20-30% to client sites from our Chicago office.

We value hands-on engineers who balance speed and reliability, and who can work closely with customers to drive practical outcomes in real environments. This is a fully engaged, high-leverage role.

Qualifications

• 3-6+ years of professional software engineering experience with ownership of production systems.
• Strong command of TypeScript, Node.js, and REST API design, including debugging and external integrations.
• Hands-on experience with AI-driven systems, tuning agent behavior and prompts based on customer feedback.
• Exceptional communication and judgment balancing speed, reliability, and real-world constraints.
• Based in Chicago with willingness to travel 20-30% to customer sites.

Responsibilities

• Lead technical delivery for customer implementations, integrations, and workflow builds; owning projects from scoping through production rollout.
• Architect and build workflows that encode real customer processes, integrating directly with their systems and adapting to edge cases.
• Develop core platform components and integration tooling to standardize reuse and scale deployments.
• Navigate complex environments and design practical solutions amid fragmented data and constraints.
• Provide field insight to product and engineering to shape the roadmap based on customer feedback.

Skills

TypeScript

Node.js

REST API design

AI-driven systems

Communication

Travel readiness

Job description

FleetWorks Technology is expanding its Chicago-based engineering team to deliver production-grade software that connects truckers with loads. You will own customer implementations, design workflows, and build scalable platform components while traveling 20-30% to client sites from our Chicago office.

We value hands-on engineers who balance speed and reliability, and who can work closely with customers to drive practical outcomes in real environments. This is a fully engaged, high-leverage role.