Staff Software Engineer, Autonomous Freight Systems

About Flexport: At Flexport, we believe global trade can move the human race forward. That’s why it’s our mission 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. Today, companies of all sizes—from emerging brands to Fortune 500s—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. Ready to tackle global challenges that impact business, society, and the environment? Come join us. 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 technolog