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Bennett Medary has held various positions in the corporate world since 2011. In that year, they were appointed as a Director of Medary Services Ltd. In 2015, they joined Airways New Zealand as a Director, Quotable Value Ltd. as a Director, and Preno as Chairman. In 2016, they became a Board Member of Coastguard Northern Region and in 2017 they joined Quotable Value Ltd. as a Director. In 2019, they took on the role of Skipper at Resolution III, and in 2021 they became President and Board Member of Coastguard New Zealand, as well as Director and Chair of PreKure, CEO and SLT Support of SMX – Email Cyber Security Specialists, and Board Advisor and Interim CEO of the same company. Finally, in 2022, they were appointed as Chief Executive of Engender Technologies Limited.

Bennett Medary attended the University of Otago from 1980 to 1984, where they earned a Bachelor of Commerce (BCom) in Information Technology. Prior to that, they attended Watching Hills Regional High School from 1974 to 1978.