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Jesse Callen has a diverse work experience spanning multiple roles and companies. Starting in 2004, they worked as a Project Manager at Callen Construction Co., Inc. until 2007. Jesse then joined Riggs Engineering as a Project Manager/Estimator from 2007 to 2008. In 2009, they transitioned to Truesdell Corporation, where they held various positions including Senior Project Manager from 2009 to 2014, Area Manager for the California Division from 2014 to 2022, Vice President - Western U.S. from 2017 to 2022, and currently holds the role of Senior Vice President.

Jesse Callen's education history begins in 1996 when they attended Ferndale High School. After graduating from high school in 1999, Jesse went on to pursue a Bachelor of Arts degree at Washington State University. During their time at the university from 1999 to 2003, Jesse studied both Business Management and Real Estate, earning a Bachelor of Arts degree in Business with a focus on these fields of study from the Washington State University - College of Business and Economics.