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Kai Sakakibara has a diverse work experience spanning various industries. In 2011, they served as the Director and Deputy President at LocationValue Inc. (Now: DearOne, Inc.) until 2018. Following a resting period, they joined Asclepia, Inc. in 2019 as the Director and CTO, later becoming the President and CEO. In 2021, they became a Guest Researcher at the University of Occupational and Environmental Health Japan. Since 2022, they have held multiple positions simultaneously, including the President & CEO of Health Data Science Inc., CTO & Director of HEALTHCARE CONSULTING Inc., and an Independent Outside Director at Kurumeshi, Inc. In the same year, they also joined Nishogakusha University as a part-time Lecturer. Kai'smost recent role is as the CTO of CareNet, Inc., starting in 2022.

Kai Sakakibara completed their Bachelor of Science in Engineering with a focus on Computer and Information Sciences, specifically neural networks, from Keio University in 2004. Kai later pursued their Master of Science in Engineering from Keio University's Graduate School of Science and Technology, specializing in the same areas of study, from 2004 to 2006.