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James O'Leonard has a diverse work experience in various roles and positions. James began their career in 1994 as a Research Associate at Harvard Business School. James then worked as a Developer Marketing at Sun Microsystems from 1996 to 1999. In 2000, they served as an Associate at Hummer Winblad Venture Partners. James then joined Zaplet in 2001, where they worked in Product Marketing until 2002. From 2002 to 2005, they held the position of VP, Marketing at Kinzan. Finally, since 2005, James has been the CEO of PEAK 15 Systems.

James O'Leonard obtained their Bachelor of Arts degree with Honors in Economics and Math from Williams College, which they attended from 1990 to 1994. James later pursued their Master of Business Administration (MBA) degree at the University of California, Berkeley, Haas School of Business from 1999 to 2001.