Balancing Autonomy and Guidance in Leadership

In 2013, when Ryan Petersen launched Flexport, he approached the problem from a customer’s perspective. Early in his career, he had worked at his brother’s import-export business, sourcing and selling ATVs, scooters, and dirt bikes from Asia to markets around the world. They built the entire technical platform to facilitate these transactions, and Ryan saw an opportunity to make the freight forwarding industry more efficient. He founded Flexport to make global trade easy and accessible for everyone and has since raised $2.3 billion to fuel the business. Today, Flexport’s platform coordinates logistics from factory floor to customer door, serving companies of all sizes. In 2023 alone, Flexport’s technology moved over $32 billion worth of merchandise. Ryan discusses how he leverages the U.S. Air Force’s OODA (Observe, Orient, Decide, Act) strategy, how AI is helping automate 1% of its freight forwarding workflows each week, and why Flexport’s agility remains the company’s greatest strength.