Tenure: Since 2016
Duties and Accreditations: Leann is a Licensed Property & Casualty Agent.
Personal: Leann and her husband Jerrel live in Wise, VA with their beloved dog Maverick. She is a graduate of Powell Valley High School and attended Mountain Empire Community College. She previously worked in the banking industry for over 8 years. In her spare time Leann enjoys playing co-ed softball, going to concerts with friends, attending sporting events, and spending time with her family.
Duties and Accreditations: Stephanie is a Licensed Property & Casualty Agent. Her job responsibilities include Claims and Policy processing.
Personal: Stephanie resides in Big Stone Gap with her husband Bo and their two children. She is a graduate of Powell Valley High School. In her spare time she enjoys baking, traveling, being outdoors and spending time with family.
Tenure: Since 2018
Personal: Rachel is a graduate of Graham Bible College where she earned her degree in General Biblical Eduation. Before coming to South-West Insurance she spent fifteen years as a teacher at Wise County Christian School. During her time at Wise County Christian she was nominated for Wise County Chamber of Commerce Forward Wise County Program and received Teacher of the Year from CEDAR of Virginia. Currently, she is an active member of Coeburn Presbyterian Church, and serves as President of Women’s Ministries for Westminster Presbytery P.C.A. Rachel spends her free time with her family and friends.
Tenure: Since 2008; Manager since 2012
Duties and Accreditations: Megan received her Property & Casualty Agent license and Life, Health, & Annuities Agent license in 2008. She also obtained her Certified Insurance Counselor designation in early 2014.
Personal: Megan received a Bachelor of Science in Business Administration, Cum Laude from the University of Virginia’s College at Wise where she was a Napoleon Hill Scholar. Her previous work experience includes academic support at UVA-Wise. Megan is an active member of Coeburn Presbyterian Church. She enjoys cooking, gardening, and exploring the outdoors.
Tenure: Since 2006; Vice President since 2013
Duties and Accreditations: Ryan is a Certified Insurance Counselor, a Licensed Property and Casualty Agent, and a Licensed Life and Health Agent.
Personal: Ryan received a Master’s of Business Administration from Appalachian State University after obtaining a Bachelor of Science Degree in Business Management and Bachelor of Arts in Mass Communications from Emory and Henry College. Prior to joining the agency he worked with the Wise County School system as Marketing teacher, Varsity baseball, and Varsity football coach at Powell Valley High School. Ryan is Past President and current member of the Board of Directors of the Big Stone Gap Kiwanis Club, Past President and member of the Board of Directors of The Gap Partnership, member of Ballad Health Lonesome Pine Hospital Board of Directors, and member of Mountain Empire Community College Foundation Board of Directors. Ryan and Wife Elizabeth reside in Big Stone Gap with their three children Katelynn, Everett and Loren.
Tenure: Since 1974
Accreditations: Masters of Business Administration and Certified Insurance Counselor since 1980.
Personal: After graduating from Powell Valley High School in Big Stone Gap, Virginia, he attended East Tennessee State University in Johnson City, Tennessee where he obtained a Bachelor of Science Degree with a major in Insurance and completed his Masters of Business Administration Degree. While attending East Tennessee State University he also completed the advanced ROTC Program, receiving a Commission as Second Lieutenant. He served in the US Army Quartermaster corps from April 24, 1971- May 31, 1974. While serving in the Army he was promoted to First Lieutenant and received the Army Commendations Metal.
Winston continues to reside in Big Stone Gap, Virginia with his wife, Judith Ann Witt. They have two children Ryan Witt and Jessica Parrott and five grandchildren, Berkley and Jaxon Parrott and Katelynn, Everett and Loren Witt. His close ties with his family, friends and community have given him insight into the needs of local businesses and the citizens of this area. Winston enjoys farming, hunting, fishing, golfing and most outdoor activities.
