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About the Role

The Autonomous Freight Systems team is a new, AI-first engineering team responsible for Flexport’s client-facing rates platform and the self-serve freight booking experience. This role is a ground-floor opportunity to shape technical direction, set up a new codebase, and build the platform that moves Flexport from an assisted-sales model to a tech-run one.

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 required to expose internal logistics data to LLMs safely.
• Navigate the rapidly evolving landscape of agent patterns, RAG, and prompt engineering to solve problems that don’t have "Stack Overflow" answers yet.
• Build and launch products rapidly and incrementally, shipping to production dozens of times per day.
• Mentor and uplevel engineers across the team, fostering a culture of technical excellence.
• Partner with the Engineering Manager to define the team’s technical roadmap and hiring bar.

Requirements

• LLM Fluency: Experience with agent patterns, RAG, and prompt engineering, understanding production viability.
• Agentic Orchestration: Experience with workflow orchestration (e.g., Temporal) and building reliable systems around non-deterministic AI.
• Entrepreneurial Drive: Ability to identify high-leverage automation problems and design AI-driven solutions without waiting for a spec.
• Product Instincts: Proven track record of building data-heavy applications with a focus on high-quality user interaction.
• Architecture Leadership: Demonstrated experience leading technical initiatives across multiple teams or systems, specifically in building unified interfaces that aggregate data from various backend systems.
• Technical Rigor: Experience building large-scale distributed systems with a preference for simple, well-tested, and extensible code.
• Technical Communication: Ability to convey technical ideas clearly to business partners, product managers, and engineers.

Skills

• Agent patterns
• RAG
• Prompt engineering
• Workflow orchestration
• Temporal
• AI agents
• LLMs
• Data-heavy applications
• Large-scale distributed systems
• Java
• Spring Boot
• Ruby on Rails
• React
• AWS
• Logistics
• Supply chain
• Freight technology
• Internal tools
• Operator-facing applications

Location

• San Francisco

Work Type

• Onsite

Experience Level

• Staff Engineer

Salary/Compensations

• $196,875—$246,094 USD

Benefits

• Bonus
• Equity
• Comprehensive benefit offerings such as medical, dental, and flexible time off

About the Company

• At Flexport, we believe global trade can move the human race forward. Our mission is to make global commerce so easy there will be more of it. We’re shaping the future of a $10T industry with solutions powered by innovative technology and exceptional people. Companies of all sizes use Flexport technology to move more than $19B of merchandise across 112 countries a year. The recent global supply chain crisis has put Flexport center stage as we continue to play a pivotal role in how goods move around the world. We are proud to have the support of the best investors in the game who believe in our mission, solutions and people.

Equal Opportunity

• All qualified applicants will receive consideration for employment regardless of race, color, religion, sex, national origin, age, physical and mental disability, health status, marital and family status, sexual orientation, gender identity and expression, military and veteran status, and any other characteristic protected by applicable law.