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W. Ryan Sampson has a diverse work experience in firefighting and emergency services. W. Ryan began their career as a Junior Member/EMT-B at the Louisa County Rescue Squad in 1999 and served until 2002. In 2001, they joined the Louisa Volunteer Fire Department as a Member of the Board of Directors and remained in this role until 2021. From 2009 to 2021, they worked as a Communications Officer (PT) at the Louisa County Sheriffs Office.

In 2011, Sampson worked as a 911 Dispatcher (PT) at the Orange County E-911 until 2016. W. Ryan then transitioned to the County of Louisa as a Firefighter/Emergency Medical Technician and later became a FF/EMT Crew Leader from 2016 to 2017. From 2019 to 2021, Sampson served as a Lieutenant, working directly with the Assistant Chief of Operations. W. Ryan was promoted to the role of Captain-Shift Commander in 2021 and subsequently became a Battalion Chief in 2022.

W. Ryan Sampson completed their high school education from 2000 to 2003 at Louisa County High School. W. Ryan pursued a degree in Agriculture, General during this time.