After graduating with a Bachelor of Arts in Computer Arts from Memphis College of Art, Westmoreland joined Pro30 funding out of Novato, California as a regional vice president and helped institute a more efficient process of packaging and selling loan portfolios on the secondary market. Over the years, Westmoreland has held many leadership roles within the finance and banking world. Most recently as the managing director of IBEX AMT spearheading the process and developing the software capable of automating the origination and underwriting of loan products. Westmoreland was the chairman of the board for general Schwarzkopf Children's Home Fund for three years. Currently Westmoreland is serving in his second year as a trustee for the US Army’s Command and General Staff College.