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Pearl Webb's work experience begins in 2011 as a Cashier at Price Chopper Supermarkets. Later, in 2013, they worked as a Summer Camp Counselor at City Union Mission. In 2014, they held positions as a CARE Specialist at H&R Block and as a Program Specialist at Camp Fire. Between 2012 and 2015, they had roles at Big Brothers Big Sisters of Greater Kansas City, first as a Recruitment Specialist and later as a Client Enrollment Specialist. In 2015, they worked as a Driver Recruiting Specialist/HR Assistant at OrTran, which was later acquired by Outwest Express. From 2016 to 2022, Pearl worked at GirtonLLL Transport, initially as a Senior Recruiter and then as a Recruiting/Talent Acquisition Manager. From 2022 to 2023, they served as a Recruiting Manager at Bulk Transport Company East, Inc., which acquired GirtonLLL Transport. Currently, they are employed as a Recruiter at Environmental Works, Inc., where they are responsible for building a recruiting program and performing full-cycle recruiting efforts.

Pearl Webb attended Park University from 2009 to 2013, where they completed their Bachelor of Arts (BA) degree in Communication Arts with a focus on Public Relations.