Staff Software Engineer, Autonomous Freight Systems

The opportunity 

The Autonomous Freight Systems team is a brand new, AI-first engineering team in San Francisco. This team will own Flexport’s client-facing rates platform and the self-serve freight booking experience—two of the highest-leverage surfaces in our Client App that dictate how clients see pricing and book freight without manual intervention.

As a Staff Engineer, you will be the technical anchor for our next-generation AI-powered rates platform. We aren't just building a UI; we are building AI agents that handle real logistics work: parsing complex rate sheets, managing pricing intelligence across ocean, air, and trucking, and making "Self-Serve" a reality for thousands of shippers. You will build the intelligence layer that allows clients to commit freight on technology alone, with no account executive and no operations touch.

This 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 for the long tail of our client base. You will partner with Pricing, Sales, Ops, and Design on hard domain problems and ship to the most-used client surfaces at the company.

You will

• 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: we ship 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.

You should have

• LLM Fluency: Experience with agent patterns, RAG, and prompt engineering. You know what works in production versus what only looks good in a demo.
• Agentic Orchestration: Experience with workflow orchestration (e.g., Temporal) and building reliable systems around non-deterministic AI.
• Entrepreneurial Drive: You don't wait for a spec; you find the highest-leverage automation problems and design the AI-driven solution.
• Product Instincts: You can identify what is worth building, not just execute on a spec. You have a proven track record of building data-heavy applications where high-quality user interaction is the priority.
• 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: A love of simple, well-tested code that is easy to extend and hard to break, combined with experience building large-scale distributed systems.
• Technical Communication: The ability to convey technical ideas in common terms to business partners, product managers, and engineers alike.

It's a plus if you have

• Experience with elements of our tech stack: Java, Spring Boot, Ruby on Rails, React, AWS.
• Experience in logistics, supply chain, or freight technology.
• Experience building internal tools or operator-facing applications.
• A bias for action: When you see a problem, you solve it.

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