Josh Lospinoso

Josh Lospinoso is the co-founder and former CEO of Shift5, an observability and cybersecurity company that protects the onboard operational technology of planes, trains, tanks, and ships. A West Point graduate, Rhodes Scholar, and Oxford-trained statistician, he spent more than a decade as an Army cyber officer building elite hacking tools for the NSA's Tailored Access Operations and the Cyber National Mission Force. Before Shift5 he co-founded RedOwl Analytics (acquired by Raytheon/Forcepoint in 2017). He wrote the C++ course that U.S. Cyber Command uses to train junior developers and turned it into the book C++ Crash Course. In January 2026 he moved from CEO to the board to focus on long-term vision while Shift5, having raised more than $180M, scaled past 130 employees.