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Stanley Buchesky has held various roles throughout their work experience. Stanley is currently the CEO of pi-top, a position they have held since May 2019. Prior to this, they served as the Managing Partner at The EdTech Fund starting in July 2017. In 2017, they also worked as the Senior Advisor for Budget & Finance at the U.S. Department of Education. Before that, they were the Managing Partner at The EdTech Fund from May 2013 to January 2017. Stanley Buchesky also has experience as a Consultant at EdTech Advisors from December 2011 to January 2017. Additionally, they served as a Trustee at Equality Charter School from July 2008 to January 2017. Earlier in their career, they held senior positions at The McGraw-Hill Companies, L-3 Communications, and Pitney Bowes, where they were responsible for mergers, acquisitions, and corporate strategy. Stanley began their career as a Captain and Infantry Officer in the United States Army, specializing in combat readiness and training.

Stanley Buchesky's education history includes a Bachelor of Science (BS) degree in Computer Science Engineering with a minor in German/French from the United States Military Academy at West Point, which they obtained from 1991 to 1995. In 2000, they pursued a Master of Business Administration (MBA) degree in Finance at Columbia Business School, which they completed in 2002. During their MBA program, Buchesky also participated in an exchange program at the London Business School in 2002, further specializing in Finance.