His work explores the intersection between digital tools and humanistic questions, particularly questions touching on the history and spaces of the American South. He earned a PhD in history at the University of Virginia in 2013, where he wrote about the geography of slavery and emancipation in the Civil War South. From 2009 until 2014 he was the associate director of the Digital Scholarship Lab at the University of Richmond. He has led digital history projects such as Visualizing Emancipation, which used a wide array of textual sources—ranging from military correspondence to runaway slave advertisements found in southern newspapers--to map out where and when slavery fell apart during the American Civil War.