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Ashley Montessoro has a diverse work experience spanning various roles and positions. Ashley began their career at Boerne Vistro Restaurant as a Hostess in 2004. In 2005, they worked as a Cook's Assistant at Episcopal Diocese of West, Camp Capers. From 2006 to 2008, they served as a Sales Associate at HMS Art and Frame Shop. During the same year, they also worked as the Arts and Crafts Director at Episcopal Diocese of West Texas, Camp Capers, where they managed arts and crafts activities, a budget, and supplies for the camp. From 2002 to 2006, they held multiple positions at Trinity Cafe, including Assistant Manager, Sous Chef, Assistant Caterer, Waitress, Busgirl, Dishwasher, and Hostess. Since 2010, they have been working at Strat Property Management, Inc., starting as a Facility Manager and subsequently progressing to various roles such as District Manager, Regional Manager, Hiring Manager - TX, Executive Administrator, Human Resources Administrator, Payroll & HR Coordinator, and Human Resources Manager. Recently, in 2023, they assumed the position of Director of Human Resources at Strat Property Management, Inc.

Ashley Montessoro pursued their higher education at the University of North Texas from 2005 to 2009, earning a Bachelor of Fine Arts degree with a focus on Metalsmithing and Jewelry. In addition to their academic achievements, Ashley has obtained several certifications throughout their career. In March 2012, they obtained the certification of Certified Self Storage Manager from the Self Storage Association. Most recently, in July 2022, they achieved the SHRM-CP certification, making their a Certified Professional in Human Resources by the Society for Human Resource Management (SHRM).