Staff AI Engineer - Autonomous Freight & Self-Serve Rates

Flexport; California (MO); On-site; USD 197,000 - 271,000; Full time

Job summary

Flexport is seeking a Staff Engineer for the Autonomous Freight Systems team in San Francisco to own its AI-powered rates platform and self-serve freight booking experiences. You will anchor the technical direction for a next-generation AI-driven system that operates across ocean, air, and trucking pricing with minimal human intervention.

You will architect, build, and ship a unified platform, mentor engineers, and partner with Pricing, Sales, Ops, and Design to deliver high-impact, data-heavy

Qualifications

• LLM Fluency with agent patterns, RAG, and prompt engineering in production environments.
• Experience with workflow orchestration and non-deterministic AI reliability.
• Proven track record of building data-heavy applications with strong user interaction.

Responsibilities

• Design and ship end-to-end AI agents that handle pricing intelligence and booking compliance without human oversight.
• Create the tooling and secure AI infrastructure to expose internal logistics data to LLMs safely.
• Navigate agent patterns, RAG, and prompt engineering to solve problems without Stack Overflow answers.

Skills

LLM Fluency

Agentic Orchestration

Entrepreneurial Drive

Product Instincts

Architecture Leadership

Technical Rigor

Technical Communication

Tools

Temporal

AWS

React

Java

Spring Boot

Ruby on Rails

Job description

Flexport is seeking a Staff Engineer for the Autonomous Freight Systems team in San Francisco to own its AI-powered rates platform and self-serve freight booking experiences. You will anchor the technical direction for a next-generation AI-driven system that operates across ocean, air, and trucking pricing with minimal human intervention.

You will architect, build, and ship a unified platform, mentor engineers, and partner with Pricing, Sales, Ops, and Design to deliver high-impact, data-heavy