Dickinson is a manager in the education practice of the Bridgespan Group and has spent the last four years as a strategic advisor to urban school districts and other education organizations across the nation. He worked in the Superintendent's Office at Providence Schools in Providence from 2009 to 2012 where he led operations, finance, and human capital initiatives. He is a graduate of Harvard College, received his MBA from University of Virginia’s Darden School of Business, and completed the Broad Residency in Urban Education. A native Rhode Islander, he lives in Providence and has two elementary school-aged children. Dickinson was one of the original champions of Teach For America’s first partnership with Providence Public Schools in 2010.