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Leo serves on the OpenLegacy Advisory Board. He has been meaningfully involved in over 50 start-ups including over 25 exits as a seller and buyer of both private and public transactions.

Leo was one of the six-person team that formed Pivotal (PVTL). During most of his time at Pivotal, he ran corporate development and strategy. He led the effort of many key initiatives including company formation, all private funding rounds, the formation of the Cloud Foundry Foundation and many customer and partner relationships.

Leo was President of Digital Island. Leo joined Digital Island as a result of a merger with Sandpiper Networks, where he was Chairman and CEO. In 2000, Leo won the Ernst & Young Entrepreneur of the Year Award for the greater Los Angeles metropolitan area.

Prior to Sandpiper Networks, Leo served as SVP and CTO of Donnelley Enterprise Solutions Incorporated. Leo was the co-founder, EVP, and CTO of LANSystems, which was sold to Intel Corporation and R.R. Donnelley & Sons Company. Leo started his first company, Integrated Analysis, while in college. He merged Integrated Analysis with LANSystems.

Leo is a graduate of the University of California, San Diego. Leo is a Trustee of the UC San Diego Foundation and is a member of the International Leadership Committee, Campaign for UCSD. He is a member of the Dean's Advisory Council at the Rady School of Management. He also the Immediate Past Board Chair of the Jewish Community Foundation of San Diego.