John Sipher

Insider Threat/Intelligence Expert

General Information

Washington, DC
Monday - Friday
Eastern Time (US & Canada)


John Sipher, Director of Client Services, CrossLead, Inc.

John Sipher is a sought-after intelligence and leadership expert.  He is a regular contributor to 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 ClandestineService in 2014. He is one of a handful of former spies who have publiclyshared their insight into the Intelligence Community. In the past few months,he has appeared on PBS NewsHour and CNN, commenting on the former British intelligenceagent who prepared the dossier on President Trump’s alleged activities in Russia.

At the time of hisretirement from CIA, John was a member of the Senior Intelligence Service, theleadership team that guides CIA activities globally. Having served multipleoverseas tours as chief of station and deputy chief of station in Europe,Russia, Asia, the Balkans, and in high-threat environments, he has significantexperience working with foreign and domestic partners to solve nationalsecurity challenges, including cybersecurity. He is the recipient of theDistinguished Career Intelligence Medal.

After retiring, John joined the McChrystal Group, anorganizational 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’sfrom Hobart College, a master’s in international affairs from ColumbiaUniversity, and has attended a variety of executive courses at HarvardUniversity, Northwestern University’s Kellogg School of Management, The AspenInstitute, and the Intelligence Community’s Executive Leadership Program.