Jacob came to Harvard with seven years of professional experience as the Director of Business Development at World Scholars. The receipt of two degrees from Yale University, Jacob was a venture creation intern at Yale Tsai Center for Innovative Thinking (formerly, "Yale Entrepreneurial Institute"), and organized one of the nation's first blockchain executive education programs partnering with Harvard and Yale law and management faculty members in early 2016. He also served as an instructional technologist at Yale College, a core member of Yale Law School Non-profit Organization Clinic, a technical assistant for Professor Akhil Amar in 2014, and a 2012 John Templeton visiting scholar. 

Jacob is the managing director of York Street Advisory. He also serves as a development consultant to a nonprofit education program funded by the US Department of Education and an education specilaist of Connecticut's renowned Youth with a Purpose program.