AI-Driven Autonomous Freight Systems Lead

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: We are building a new engineering team in San Francisco to own our client facing rates platform and the self-serve freight booking experience. These are two of the highest leverage surfaces in our Client App: how clients see pricing and how they book without manual intervention. Rates sit at the center of every freight decision. You will lead the Autonomous Freight Systems team, owning the systems that power rate visibility, quoting, and pricing intelligence across ocean, air, and trucking. You will extend that work into a fully self-serve booking flow for smaller shippers: clients who commit freight on technology alone, with no account executive and no operations touch. This is a ground-floor opportunity to build the platform that moves Flexport from an assisted-sales model to a tech-run one. You will lead an AI-first engineering team tasked with automating the complex logic of quoting and booking. This means not just building software, but building autonomous systems and AI-powered workflows that eliminate the need for manual intervention in the shipping lifecycle. You will: Recruit, build, and lead a new engineering team with a heavy focus on AI-driven automation and intelligent system design. Partner with leadership to define how LLMs and agentic workflows can be applied to logistics pricing and customer interactions. Participate in critical technical discussions regarding AI model integration, data repair agents, and automated quality safeguards. Represent your team with leaders across different parts of the organization. Participate in critical technical design and product discussions. Invest in the development and coaching required for each team member’s success. Manage, measure, and communicate the team’s progress toward goals. Partner closely with cross-functional stakeholders to define the team’s roadmap. You should have: AI/Automation Vision: Demonstrated ability to lead teams building intelligent systems, ideally involving LLMs, automated decision engines, or AI agents in production. Strategic Roadmap: Experience moving a business from human-led processes to autonomous, software-driven ones. Bachelor’s degree in Computer Science or equivalent practical experience. 5+ years of engineering experience with a strong technical background. 2+ years of experience managing engineering teams directly. Product Engineering Expertise: A proven track record of building complex, data-heavy applications where high-quality user interaction is the priority. Platform Thinking: Experience building unified interfaces that aggregate data from various backend systems into a cohesive user experience. Growth Leadership: Experience building and scaling teams from an early stage, including a demonstrated ability to hire, develop, and retain high-performing engineers. Clear Communication: The ability to translate between technical constraints and business goals for stakeholders. It’s a plus if you have Experience in logistics, supply chain, or freight technology. Experience with elements of our tech stack: Java, Spring Boot, Ruby on Rails, React, AWS. Experience managing distributed or hybrid teams. The range displayed on each job posting reflects the minimum and maximum target for new hire salaries for the position in the posting's respective region. Our salary ranges are determined by role, level, and location. Within the range displayed, individual pay is determined by work location and additional factors, including job-related skills, experience, and relevant education and / or training. The US base salary range for this position (this does not include bonus, equity and benefits): $206,016 - $257,520 USD Commitment to Equal Opportunity At Flexport, our ability to fulfill our mission of making global commerce easy and accessible relies on having a diverse, dedicated and engaged workforce. 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