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Jesse Conklin has a diverse work history with experience in engineering and property management. They worked as a Chief Engineer for Unilev Management since December 2020. Prior to that, they served as Director of Engineering at Hotel Ivy, a Luxury Collection Hotel from June 2018 to December 2020. Before that, they held the positions of Director of Engineering and Engineer 3 at Vail Resorts from September 2014 to June 2018. Jesse Conklin began their career as a Residential Property Manager at Hawaiiana Development Group, where they worked from May 2007 to August 2014.

Jesse Conklin received a Certificate in Welding Technology/Welder from Kauai Community College in the year 2012. Prior to that, from 2000 to 2002, they attended South Central College and obtained Certificates in Small Engine Mechanics and Repair Technology/Technician.