Jason Greenawalt serves as the CEO of the Nakupuna Companies and President of Na Aliʻi Consulting. He is also the Vice Chair and Treasurer of the Nakupuna Foundation – the majority owner of all Nakupuna Companies. With an endless commitment to maintaining a start-up culture and a general irreverence for bureaucratic hierarchy, Jason can often be found elbow-deep with any one of our project teams developing unique and self-proclaimed “elegant” solutions to address a client’s business or mission needs. When the deadlines are tight, Jason orders the late-night pizzas for the team and keeps them motivated by pulling inspirational quotes as needed from his favorite luminaries, such as Abraham Lincoln, Jim Collins, or Ron Swanson.  

Prior to joining Na Aliʻi, Jason spent more than a decade in public service with the Department of the Navy (DON), most recently serving as the Director of Business Operations in the Office of the Deputy Under Secretary of the Navy for Management. There, Jason led efforts to transform the DON’s business operations, streamline business processes, and reduce operating costs, and was responsible for the oversight, portfolio management, and funds certification of nearly 500 defense business systems with an annual cost of nearly $1.2B. Jason’s other positions with the Navy cut across the organization to include serving on the staff of the Deputy Chief of Naval Operations for Fleet Readiness and Logistics (OPNAV N4); first as the lead for Strategic Planning, then as the Chief of Staff for the Energy and Environmental Readiness Division. His other positions included a variety of roles at both the Naval Air Systems Command (NAVAIR) and Commander Navy Installations Command (CNIC).  

Jason is proud to have been on the ground floor to oversee the growth of the Nakupuna Companies – from a single firm with a handful of associates to a family of companies with more than a thousand employees working across the United States. Jason is principally responsible for the long-term vision of the Nakupuna Companies and oversees much of the daily operations, but his real passion is matching complex business problems with the right innovative professionals that possess unwavering optimism and commitment to solve those problems – all while delivering tailored solutions that are always a little different than the norm.  

Jason is extraordinarily passionate about supporting the Native Hawaiian community and furthering the vision his father-in-law, Warren Nakupuna Ah Loo, had when he founded Na Aliʻi. As a board member of the Nakupuna Foundation, Jason plays an active role in developing and approving the overall strategy of the portfolio of charitable investments. 

Jason has completed the Advanced Finance Program (AFP) at the Wharton School and holds a Masters of Public Policy (MPP) from the George Washington University along with executive certifications from the Kenan-Flagler Business School, the Naval Postgraduate School, and the Elliott School of International Affairs. He is also a distinguished alumnus of Campbell University and a proud graduate of the Federal Executive Institute.