Bob “Masa” Matsuoka, as the Head of Engineering and Technology for the Core brand at Tripadvisor Media Group (NASDAQ: TRIP), has been a driving force in the tech industry. His journey with Tripadvisor began in 2016 after the acquisition of his startup, Citymaps. Masa’s expertise and leadership quickly propelled him through various roles, from Director overseeing Maps, Places, New Ventures, and Trust and Safety, to Senior Director of Engineering, managing Engineering Operations and Global Workforce to VP of Product Engineering and the B2C Leadership Team. His current position as the supervisory head of all Engineering and Technology for the Tripadvisor brand places him directly under CEO Matt Goldberg on the Executive Leadership Team. Masa’s tenure at Tripadvisor is distinguished by his significant contributions to globalizing the engineering workforce and leading major projects such as the architectural design for the Tripadvisor social project, the launch of Reco, Calypso, and the integration of the Citymaps Maps stack. He also spearheaded Crowdfree, a volunteer-driven initiative to assist travelers during the pandemic. 

Leadership comes first, then tech after that. It’s about being a leader first, with a solid foundation in tech, but not leading with the tech.

Before his impactful involvement with Tripadvisor and Citymaps, Masa served as a fractional CTO in New York City, guiding startup founders in developing technology teams and roadmaps. His entry into the NYC tech scene began with founding RunTime Technologies, a CMS startup, during the early days of “Silicon Alley.” Born to Japanese and Australian parents and raised in a multicultural environment, Masa’s diverse background has been a cornerstone of his approach to technology and leadership. Currently residing in Hastings-on-Hudson, Westchester, with his partner Joanie, Masa is a father to two daughters, Lily and Autumn. His interests extend beyond technology to gardening, travel, snowboarding, hiking, and music, where he showcases his talent as the bassist of a Go-Go’s cover band. 

ROBERT'S CONTENT


Podcast: Leading with Insight: A Tech Odyssey


Join us in a compelling conversation with Robert Matsuoka, where he unveils his transformative journey from a tech-centric role to a strategic leadership position. In this episode of CTO Confessions, Robert delves into the art of delegation, the…

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