How Amazon’s CFO ‘shatters’ expectations and helped power the company to No. 1 on the Fortune 500

Good morning. A brand new Fortune 500 list is out this morning. Amazon eclipsed the $700 billion mark with a 12% jump in revenue in 2025 and took the No. 1 spot, ending Walmart’s historic 13-year run. And Amazon’s SVP and CFO Brian Olsavsky has led finance for over a decade with a front-row seat to the company’s rise on the list. Amazon debuted on the Fortune 500 in 2002 at No. 492. That’s the same year Olsavsky joined the company. More than 20 years ago, the now tech giant was a fraction of Walmart’s size; today, its multi-engine model, spanning e-commerce, logistics, AWS, and a fast-growing advertising business. Walmart fell to No. 2 on the list for the first time since 2012. At Amazon, led by CEO Andy Jassy, the result is not just a new revenue leader, but a reshaped definition of what a “retailer” looks like in the age of cloud computing and AI. As CFO, Olsavsky has been a strategic partner to Jassy throughout. Central to that evolution has been Olsavsky’s own trajectory at the company. He became finance chief in June 2015, previously serving as VP of finance and CFO for the global consumer business. Before that, he was VP of finance for Amazon’s North America retail business unit and acquisitions, and he started at the company leading the finance departments for Amazon’s Worldwide Operations organization. He spent much of his tenure under the leadership of Jeff Bezos, CEO of Amazon from the company’s founding in 1994 until 2021, when he stepped down and was succeeded by Jassy. Over the past 20 years, Amazon has had several major ups and downs. It weathered the 2008 financial crisis, heavy investment cycles that depressed earnings and spooked investors in the early 2010s, a roughly 50% stock decline in 2022 amid inflation and post-pandemic pullback, and an AWS slowdown in 2022–2023. Through all of it, the long-term trajectory has been strongly upward. As finance chief, Olsavsky has had to navigate