Holly became interested in birds through her work with Rainforest Biodiversity Group. Serving as president, she helped the group fundraise and manage their conservation projects. She holds a B.S. in Wildlife Ecology from the University of Maine and an MSc in Conservation Biology and Sustainable Development from University of Wisconsin-Madison. She collaborated with BirdsCaribbean to launch the Caribbean Birding Trail (CBT), a project that seeks to conserve the region's natural heritage, and went on to become the CBT's Project Manager.