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Overnight Finance Rotational Development Program Jobs in Illinois

Flexport

Rotational Development Program

Chicago, IL · On-site

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 ...

Flexport

Rotational Development Program

Chicago, IL · On-site

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 ...

Flexport

Rotational Development Program

Chicago, IL · On-site

$60 - $80/hr

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 ...

Flexport

Rotational Development Program

Chicago, IL · On-site

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 ...

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Infographic showing various Overnight Finance Rotational Development Program job openings in Illinois as of August 2026, with employment types broken down into 1% As Needed, 75% Full Time, 21% Part Time, and 3% Contract. Highlights an 95% Physical, 1% Hybrid, and 4% Remote job distribution.

Rotational Development Program

Chicago, IL • On-site

Flexport
Trucking • 1 - 5K employees
Learn more about Flexportexternal

Full-time

Posted 4 days ago

Flexport rating

4.4

Company rating: 4.4 out of 10

Based on 11 frontline employees who took The Breakroom Quiz

Job description

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.

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