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Jim Estramonte's work experience includes serving as the Chief Executive Officer at Starmount Healthcare Management starting in May 2022. Before that, they had a long career in the U.S. Coast Guard, starting in May 1993 and concluding in September 2022. In the Coast Guard, they held various roles such as Career - Officer, Chief of Staff to Vice Admiral, Commanding Officer of Coast Guard Cutter MUNRO, Chief of Resource Management in the Office of the CFO, Commanding Officer of Coast Guard Cutter VIGILANT, Executive Officer of Coast Guard Cutter RUSH, and Financial Analyst at Coast Guard Headquarters. Furthermore, they worked as a Senior Military Fellow at the Center for a New American Security from August 2015 to July 2016 and as the Military Assistant to the Secretary of Homeland Security at DHS until August 2015.

Jim Estramonte completed their Bachelor's degree at the US Coast Guard Academy from 1989 to 1993. Jim then pursued a Master of Business Administration (M.B.A.) degree at George Mason University from 2004 to 2006.