---
title: 'Rotational Development Program at Flexport'
canonical: 'https://feeny.ai/job/rotational-development-program-flexport-chicago-illinois-eexct2q6sv1t'
type: 'job'
last_seen: '2026-09-09'
---

# Rotational Development Program at Flexport

- **Company:** Flexport
- **Location:** Chicago Illinois, United States
- **Posted:** 2026-09-04
- **Last confirmed live:** 2026-09-09
- **Apply:** https://job-boards.greenhouse.io/flexport/jobs/8172300

## Job description

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.

Build the operational and technical skill set that runs global trade

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.

## What you'll do

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

This role is for you if you

- 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.

Ready to build the future of global trade — and the skill set to run it?

Apply now.

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. 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.

Global Data Privacy Notice for Job Candidates and Applicants

Depending on your location, the General Data Protection Regulation (GDPR) and California Consumer Privacy Act (CCPA) may regulate the way we manage the data of job applicants. By submitting your application, you are agreeing to our use and processing of your data as required. Please see our Privacy Notice available at [www.flexport.com/privacy](http://www.flexport.com/privacy) for additional information.

## About Flexport

## Company Overview
- **One-liner**: Flexport is a technology-driven freight forwarding and supply chain platform that uses AI to coordinate global logistics from factory to customer door.
- **Entity Type**: Private (Series E)
- **Headquarters**: San Francisco, California, USA
- **Founded**: 2013
- **Founders**: Ryan Petersen

## Core Business
- **Primary industry**: Logistics, Supply Chain Technology, Freight Forwarding
- **Target customers**: B2B — enterprise and SMB businesses that import/export goods globally across industries
- **Mission or purpose statement**: "To make global trade so easy there will be more of it."

## Products & Services
- **Ocean & Air Freight**: Full-service ocean and air freight solutions with SKU-level visibility, real-time tracking, and cost management.
- **Customs Brokerage**: Licensed customs brokers using AI to review 100% of entries before submission, achieving a compliance error rate 10x better than next best in class.
- **Booking Management**: Platform to manage ocean contracts and bookings, track real-time performance, and optimize allocation strategies.
- **Buyer’s Consolidation**: Service to maximize container utilization by grouping multiple suppliers into one container, reducing freight and labor costs.
- **Supply Chain AI Platform**: AI-driven decision-making platform that automates processes, reduces freight spend by 10% or more, and deploys large language models and AI agents for real-world logistics optimization.

## Market Standing
- **Valuation/Market Cap**: Not publicly disclosed (private company)
- **Key Metric**: 2.9x net revenue growth since 2024; serves more than 13,000 customers across 147 countries
- **Notable Investors/Partners**: Ryan Petersen (Founder & CEO); major investors include Founders Fund, SoftBank Vision Fund, and others (specific lead investors not fully detailed in provided sources)
- **Growth Signals**: Rapid AI deployment in logistics; 400+ software engineers focused on AI; net revenue growth of 2.9x since 2024; expanding global presence with offices worldwide

## Competitive Advantages
- **Real-world AI deployment**: Unlike many supply chain AI startups, Flexport is deeply embedded in actual operations of moving cargo by ocean, air, truck, and rail, with proprietary data and integrations.
- **Scale and trust**: 13,000+ customers and integration with enterprise systems, logistics service providers, and governments.
- **Customs compliance**: AI auditor reviews 100% of entries, achieving 10x better error rate than next best in class.
- **End-to-end platform**: Single platform covering freight, customs, booking, and consolidation, reducing silos and complexity.
- **Data ontology**: Proprietary data ontology for global logistics, enabling powerful AI models.

## Strategic Focus
- **AI-driven autonomous supply chain**: Building AI agents to create an autonomous supply chain, deploying the latest foundational AI models on top of proprietary data and integrations.
- **Customer obsession**: Prioritizing customer success and hard cost savings (e.g., 10%+ reduction in freight spend).
- **Global expansion**: Operating across continents and time zones, with offices in multiple global locations.
- **Talent development**: Aiming to hire 80% of manager and above roles from within, developing early-career talent into leaders.

## Why Work Here
- **Meritocracy**: Compensation and advancement based on value created, with rapid growth opportunities for smart, hardworking people. Many leaders started on the ground floor.
- **Learning environment**: Described as "the best company to learn about how the world works" — logistics underlies the global economy. Employees speak over 70 languages.
- **Cutting-edge technology**: 400+ software engineers deploying latest AI models in real-world logistics; roles include Senior Software Engineer: Applied AI, Autonomous Freight Systems, and Data Infrastructure.
- **Culture**: Values include "Win as a Team," "Empower the Client," "Play the Long Game," "Act Like an Entrepreneur," and "Simplify." Recognized as a Great Place to Work.
- **Global and remote-friendly**: 125 open positions across Engineering, Operations, Sales, Customs, and more, with offices worldwide and remote options.
- **Impact**: Working on the $8.6T global logistics market — "the single largest opportunity to apply AI anywhere in the world."

## Sources
1. [flexport.com](https://www.flexport.com/company/careers/)
2. [flexport.com](https://www.flexport.com/)
3. [flexport.com](https://www.flexport.com/company/about-us/)
4. [flexport.com](https://www.flexport.com/careers/jobs/)
5. [flexport.com](https://www.flexport.com/careers/jobs/?gh_src=c0d6caef1)

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