Summer Engineering Rotational Program Jobs in Chicago, IL

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.

At Flexport, we believe global trade can move the human race forward. We're shaping the future of a $10T industry with technology and people who understand it end to end. The Rotational Development Program (RDP) exists because that combination — real supply chain fluency plus the ability to build and automate — doesn't exist at scale in the market today. So we're building it ourselves.

This is an 18-month program, not a rotation for rotation's sake. Every assignment is live, revenue-generating work. Every participant leaves with a certification in AI and low-code tooling running alongside their operational and commercial training. And every graduate places into a role with real scope: primarily Account Management, with paths into Automation Engineering, Forward Deployed Engineering/Consulting, Sales Engineering, or a traditional Ops/Sales/Customs track.

You’ll rotate through three functions, six months each, with AI/low-code curriculum running continuously across all three:

• Gateway Ops (Air or Ocean). Own the shipment lifecycle. Execute bookings, manage exceptions, and hold data integrity to Flexport's standard. Build your first automation and reporting skills through structured coursework running in parallel.
• Customs. Become a global trade expert by navigating the complex world of customs regulations to ensure goods comply with international laws. Simultaneously, move into applied technical work: SQL, workflow automation, Lean process improvement, etc.
• Sales / Account Management. Take on go-to-market work and build client-facing skills, operating with more independence. Your capstone: identify a real business problem in the function you're sitting in and build the tooling or process fix that solves it. You'll present it to leadership at graduation.

• A day-to-day manager in your current rotation and a Rotation Program Manager tracking your development, with mid-point and end-of-rotation evaluations at every stage.
• Certifications in AI/low-code tooling, from foundational bootcamp through applied builds to a capstone project.
• Bi-weekly cohort touchpoints and a standing alumni mentor community.
• Increased earning potential as you clear program benchmarks

• Are on track to graduate, or recently graduated, and want to build a career at the intersection of supply chain operations and technology — not just run one or the other.
• Are genuinely curious about AI and low-code tooling and want to build real fluency, not just check a resume box.
• Can operate with minimal supervision, prioritize a high volume of work, and communicate clearly under pressure.
• Want real ownership fast? This program hands you live client and business work from the very beginning — it is not a shadowing or classroom based program.
• Have a "compliance-first" mindset. We operate in a heavily regulated industry, and that matters in every rotation.

At Flexport, our ability to fulfill our mission of making global commerce easy and accessible relies on having a diverse, dedicated and engaged workforce. 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.