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Yossi Ben Ishay has worked in various roles in the technology industry since 1999. Yossi began their career as an Instructional Design/Course Director for the Israeli Air Force, where they were responsible for administering the learning management system, mentoring and guiding new instructors, and commanding and training technicians to maintain electronic systems of classified system weapons. In 2004, they moved to Ben Gurion Airport, where they managed the training and readiness management system, developing courseware, presentations, tests and simulations, and generating reports analyzing competency levels for department managers. From 2008 to 2018, they worked at Britannica Knowledge Systems, first as a Senior Product Manager, then as an Executive Director of Product Management. In this role, they were responsible for a cloud based system for resources, scheduling optimization, training and qualification management in the airline, military, corporate, homeland security, and banking markets. Yossi then joined Centrical in 2018, where they served as VP Product Management. Centrical is the next-gen employee engagement and performance management platform. In 2022, they joined Kissterra as VP Product Management.

Yossi Ben Ishay attended Holon Institute of Technology from 2005 to 2008, where they obtained a B.A in Instructional Systems Technologies.