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John Sipher, Director
CrossLead, Inc.

John Sipher is a sought-after cybersecurity and intelligence expert. In 2016, John reviewed The Secret History of Cyber War by Fred Kaplan (Simon & Schuster) for Lawfare, a national security blog. He is a regular contributor to the national security website “The Cipher Brief,” and serves as a media expert on issues related to intelligence and national security.

John retired after a 28-year career in the Central Intelligence Agency’s National Clandestine Service in 2014. He is one of a handful of former spies who have publicly shared their insight into the Intelligence Community. In the past few months, he has appeared on PBS NewsHour and CNN, commenting on the former British intelligence agent who prepared the dossier on President Trump’s alleged activities in Russia. 

At the time of his retirement from CIA, John was a member of the Senior Intelligence Service, the leadership team that guides CIA activities globally. Having served multiple overseas tours as chief of station and deputy chief of station in Europe, Russia, Asia, the Balkans, and in high-threat environments, he has significant experience working with foreign and domestic partners to solve national security challenges, including cybersecurity. He is the recipient of the Distinguished Career Intelligence Medal.

After retiring, John joined the McChrystal Group, an organizational management consultancy founded by Gen. Stanley McChrystal (Ret.). In 2016, John shifted to a McChrystal Group spinoff, CrossLead, which focuses on leveraging software.

Currently, John is the director of client services at CrossLead, a consulting and software firm focused on organizational improvement and culture change. 

John has a bachelor’s from Hobart College, a master’s in international affairs from Columbia University, and has attended a variety of executive courses at Harvard University, Northwestern University’s Kellogg School of Management, The Aspen Institute, and the Intelligence Community’s Executive Leadership Program.