Lives of Consequence
John R. Sipher '83, P'19
Retired, Central Intelligence Agency
John Sipher retired from the Central Intelligence Agency in 2014 as a member of the Senior Intelligence Service, the leadership team that guides CIA’s global activities. During his 28-year tenure in the agency’s National Clandestine Service, Sipher served multiple tours overseas, working with foreign and domestic partners to solve national security challenges.
In 1986, Sipher joined the clandestine service, which aims to strengthen national security and foreign policy through the collection of human intelligence and covert operations. Over the subsequent years, he served as Chief of Station and Deputy Chief of Station in Europe, Asia, Southeast Asia, the Balkans, and South Asia. The recipient of the CIA’s Distinguished Career Intelligence Medal, Sipher also served as a lead instructor in the agency’s clandestine training school, and as a regular lecturer at its leadership development program.
As project lead with the McChrystal Group, an organizational management consultancy founded by Gen. Stanley McChrystal, Sipher worked with clients on leadership, managing cultural change and building cross-functional teams. In 2016, Sipher helped establish a spinoff, CrossLead, Inc., where he is currently director of customer success. Utilizing cloud-based software and talented consultants, CrossLead develops tools for corporate leadership to efficiently scale organizations and increase performance.
Sipher earned a master’s in international affairs from Columbia University and has attended a variety of executive level courses at Harvard University, Northwestern University’s Kellogg School of Management, Aspen Institute and the Intelligence Community’s Executive Leadership program.
As a student at HWS, Sipher was a member of the Druid Society, president of Kappa Sigma fraternity and captain of the Hobart lacrosse team, which won four consecutive national championships while he was a player. He also studied abroad in London with Professor Emerita of English Claudette Columbus and Professor of Sociology Jack Harris. Sipher’s mother, Ann, graduated from William Smith in 1956, and his son, William Sipher ’19, is currently studying physics.
As an expert on national security and intelligence issues, Sipher has appeared on the PBS News Hour and is a regular contributor to The Cipher Brief, a digital security-focused news and analysis platform. He has shared his experience and insight with HWS students during the Colleges annual Day on the Hill program.