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Chadd Crosson has a diverse work experience. From 2011 to 2014, they co-founded and ran a driveway sealing company called Coated With Care. Chadd was responsible for daily operations, including proposing services to customers and generating estimates.

In 2015, Chadd joined GIS Benefits, Inc., where they started as a Sales Specialist. In this role, they assisted the sales team in acquiring new business, managed broker relationships, communicated with insurance carriers, and ensured accurate quoting for broker clients. Chadd compared insurance products and quotes to determine the best options for clients. Chadd was promoted to Account Executive in September 2017, and in August 2019, they transitioned to the position of Regional Sales Manager.

Chadd Crosson has a Bachelor's Degree in Business Administration and Management, which they obtained from Saint Leo University in the period of 2012-2015. In addition to their degree, Chadd earned a Florida 2-15 Life, Health, and Variable Annuities License in May 2014. Before attending university, Chadd completed their high school education at Greely High School from 2008 to 2012. During their time at university, Chadd also had the opportunity to study Business Management at the International College of Management Sydney (ICMS) in 2014 and at Universitat Autònoma de Barcelona in 2013.