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Rotational Development Program

Flexport Chicago, Illinois, United States Full-time Account Management Posted Oct 13, 2026
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Culture signals in this specific role

Inferred from the employer’s wording in this job description. These role-level signals are separate from the company-wide employee-review scores below.

OwnershipThe description emphasizes ownership or end-to-end responsibility.
Customer-facingThe role includes direct customer or client interaction.
MentoringMentoring, coaching, or technical leadership is part of the role.

What it’s like to work at Flexport

Global Trade & Logistics Platform · San Francisco

3.5
Employee Rating
3.6
Work-Life Balance
190
Open Roles
ship-fastproduct-impactlearning

What employees love

  • Entrepreneurial culture — motivated, intelligent colleagues building the OS for global trade
  • Real product impact in a complex domain with global cross-functional collaboration

What could be better

  • Multiple layoff rounds since 2022 and top-down decisions that bypass engineering input
  • Mandatory 5-day return-to-office policy introduced in 2025
View full Flexport culture profile →

About the Role

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:

Throughout the program, you'll get:

This role is for you if you

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 for additional information.

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Frequently Asked Questions

What is the work-life balance like at Flexport?
Flexport has a work-life balance score of 3.6/5 based on employee reviews. This is about average for the AI/tech industry.
What is Flexport’s culture like?
Flexport is characterized by these culture values: ship-fast, product-impact, learning. Based on employee reviews, the company has an overall rating of 3.5/5. Entrepreneurial culture — motivated, intelligent colleagues building the OS for global trade
How many open roles does Flexport have?
Flexport currently has 190 open roles across departments including engineering, product, sales, and more. Roles are refreshed daily from their careers page.
Is this role remote-friendly?
This role is located in Chicago, Illinois, United States. Check the job description above for specific location and remote work details.
Apply for this role at Flexport →