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Yossi Gabay has a diverse work experience in technology and leadership roles. Yossi started their career in 1996 at Israeli Military Intelligence - Unit 8200, where they held various positions including Head of Cyber and CIO. In 2005, they joined the Israel Defense Forces as the Head of an elite R&D Unit, responsible for managing a large software development organization. Yossi later worked at XOR as the VP of Business Development & Cyber. Yossi then joined Bank Leumi as the Head of Digital and Technological Development, and later as the Head of IT Infrastructure. In 2013, Yossi co-founded CYREBRO and was also appointed as the VP of Technology at Dan Hotels Israel.

Yossi Gabay obtained an Engineer's degree in Electronic Engineering from Lev Academic Center from 1988 to 1992. Yossi then went on to earn a Master's Degree in Communication and Technology in Education from Bar-Ilan University between 1993 and 1997. In 2000, Yossi completed an academic-military education program at the Israel Army IDF- The Interdepartmental College for Command and Headquarters, earning the rank of Lieutenant Colonel. Finally, in 2007 and 2008, Yossi pursued a Master of Business Administration (M.B.A.) in Management from Tel Aviv University.