The Uncommon Path | Sunny Bedi on Building AI for the CIO

CIOs often sit at the center of company transformations. They are asked to make sales faster, finance sharper, legal safer, and engineering more productive, while keeping decades of systems, processes, and workarounds running underneath it all. And yet, no one seems to be building for them. Sunny Bedi, co-founder of Whirl AI, knows that seat and the challenges that come with it well. After leadership roles at NVIDIA, VMware, Snowflake, and GitLab, he started Whirl AI to build for the people responsible for making enterprise change actually work. In this episode of The Uncommon Path, Sunny joins Matt Jacobson to talk about the hidden complexity inside enterprise systems, why technical debt slows down innovation, and what it means to build AI for the office of the CIO. They also discuss Sunny’s lessons from Jensen Huang and Frank Slootman, including the “speed of light” mindset that continues to shape how he builds. The Uncommon Path offers a behind-the-scenes look at the choices, conviction, and lived experience behind company building. Timestamps: 00:00 Building for the CIO 01:52 Sunny’s path through enterprise technology 05:01 The idea behind Whirl AI 08:20 Understanding the current state 12:17 Technical debt and speed 15:43 Why the CIO could use better tools 17:37 Reimagining enterprise transformation 18:51 Why Sunny partnered with ICONIQ Stay connected: Follow us on LinkedIn: https://bit.ly/3V8wH0b Follow us on X: https://bit.ly/4874SwQ Explore ICONIQ Insights: https://bit.ly/45Vj22R Disclaimer: iconiq.com/outreach-disclaimer