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Stick Crosby has a diverse work history starting in 2007 as a Technician at Wyoming Machinery Company. From 2011 to 2013, Stick worked as a Firefighter for the town of Mills, followed by a role as a Volunteer at the Fraternal Order of Eagles until 2015. Stick then joined Community Health Centers Of Central Wyoming as a Building Superintendent from 2013 to 2015. Stick's healthcare journey began in 2015 at AllCare Health, where they held various roles including Network & Health Equity Manager, Director of Network and Health Equity, and Sr. Director of Provider Network and Health Equity. Currently, Stick is working at Lucet (formerly New Directions + Tridiuum) as the Director of Provider Strategy since June 2023.

Stick Crosby earned an Associate of Science (A.S.) degree in Fire Science/Firefighting from Casper College in 2008-2010. Later, Stick obtained a Bachelor of Innovation and Leadership degree in Business Administration and Management from Southern Oregon University in 2022-2024. Stick further pursued a Master of Business Administration (MBA) in Business Administration and Management from Southern Oregon University in 2023-2025. In addition to Stick's formal education, they have obtained certifications including Microsoft Office Specialist: Excel Associate (Office 2019) from Microsoft in 2023, and the certifications "OneNote 2016 Essential Training" and "Access Basics for Excel Users" from LinkedIn in 2022.