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# Rotational Development Program

- **Company:** Flexport Inc.
- **Location:** Chicago, IL, United States
- **Contract:** Permanent contract
- **Skills:** Artificial Intelligence, Data Integrity, Remote Desktop Services, SQL Databases, Low-code
- **Published:** November 4, 2026
- **Apply:** https://www.careerbuilder.com/job-details/rotational-development-program-chicago-il--96827488-96bd-461f-a36c-8ce26a83ebc1

## About the Role

* 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.

## Description

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.

Throughout the program, you'll get:

 * 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