Lily is from Southbury, CT. She completed her undergraduate studies at Dartmouth College, where she majored in Government and Psychology. After college, Lilly served as a Peace Corps volunteer on the Eastern Caribbean island-nation of Saint-Lucia. During her service, Lilly established Brownies and Girl Guides troops to teach young girls and mothers about HIV Prevention and Healthy Lifestyles. A violinist for 20 years, Lilly also created the island's first Village Orchestra to teach at-risk youth to play string instruments as an income-generating skill. After Peace Corps, Lilly returned to graduate school at the University of Pennsylvania. She graduated in 2011 with a Master's degree in Public Administration, a Master of Science in Social Policy, and was selected as a finalist for the Presidential Management Fellowship.