Michael Stapleton is a Technical Program Manager at Bestow, where they focus on transforming insurtech through strategic initiatives. With over 16 years of experience in managing enterprise-scale transformations and multimillion-dollar portfolios, Michael has a proven track record of improving operational efficiency and driving faster project deliveries. Previously, they served as an IT Project Manager at NAVWAR, leading high-performing teams in complex technology transformations. A Navy veteran, Michael has also held significant roles, including Tactical Systems Officer on the USS Louisiana and Captain/Owner of Gnarly Goat Charters. They hold a BS in Oceanography from the US Naval Academy and have completed advanced studies at Harvard Kennedy School.
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