The opportunity

Join the Office of the CEO and work directly on Flexport's highest-priority problems alongside the CEO, the President, and the leaders who run our regions and modes of freight. You will pick up a mode or a region, ocean, air, trucking, omnichannel, or customs, and learn it from the inside by solving real problems in it. Pricing in a mode that is losing money. Why a region misses its plan. Whether we buy, build, or partner.

Then you go run part of it. Some people in this role move into a business unit as the number two to the leader who runs it. Some stay at the center and take on more scope. The operating job at the end is the point of the role, not a side benefit.

You will:

• Own our biggest open questions end to end and come back with recommendations the CEO can act on.
• Build the analysis yourself. Pull the data, build the model, find the error before someone else does.
• Go to where the work happens, from warehouses and ports to a customer's supply chain team. Opinions about freight formed in a conference room are usually wrong.
• Run the operating cadence for a freight mode or region. Weekly metrics, quarterly plan, and the follow-ups nobody wants to chase.
• Get things unstuck, which often means finding the four people who need to agree and getting them in a room.
• Use AI on everything and automate your own job as you learn it.

You should have:

• 4 to 6 years in investment banking, private equity, management consulting, a high-growth operating role, or running your own company. Founders who shut it down are welcome. Tell us what broke.
• The ability to build a financial model from a blank sheet and defend every cell.
• A track record of taking an ambiguous problem, doing the research, and turning it into a recommendation a senior leader can act on.
• Relentless curiosity about how physical goods move. Freight is messy, old, and full of edge cases. That should sound interesting to you, not tedious.
• Clear, short writing and the judgment to influence people more senior than you.
• A compliance first attitude. We operate in a heavily regulated industry and our regulators matter to us.

This is not for you if:

• You want to stay in strategy. Every one of these seats is a path into an operating job.
• You need a fixed scope. The scope changes when the business changes.
• You want to work remotely. You need to be in the room.

You will get:

• Direct exposure to the CEO and the executive team from week one.
• A real operating job at the end of it, not a vague promise.
• The fastest way we know to learn how global trade actually works.

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