This article is part of our collection about the 2019 state of IT. Click here for more.The exciting, albeit chaotic corporate culture that many digital-native companies are known for doesn’t just appeal to younger employees with little memory of life before the Internet. It’s also quite attractive to experienced executives—and that includes CIOs.In fact, in recent years a number of leading digital-native companies (generally founded after 1995) have hired their first-ever global CIOs. The decision to do so typically happens around the time their annual revenue falls in the $500 million to $1 billion range. At that point, the company has grown geographically, offers a complex mix of products and/or services, engages with a big number of vendor partners, and uses a growing suite of technologies.Many of the CIOs who join these companies come from the ranks of the Fortune 500, where they have headed the primary technology function and are considered the unquestionable expert in their discipline. On the other hand, almost everyone is seemingly a tech expert at a digital-native company.Yet CIOs remain undeterred.“The change has been refreshing and exciting,” said Zoom CIO Harry Moseley, who left his role as KPMG CIO to join the video communications company in early 2018. “The entrepreneurial culture that our founder and CEO, Eric Yuan, has established is amazing. The culture is open and transparent, and we have a biweekly all-hands meeting with every member of the company around the world. Every question that gets asked is owned and answered by a member of the executive team.”Another reason why “trading down” is attractive lies in the opportunity for CIOs to test their skills in terms of becoming more agile and building a technology infrastructure from the ground up.From the reverse perspective, what do digital-native companies hope to gain by hiring these experienced CIOs? Experts have boiled it down into four main buckets.