Short attended Northfield Mount Hermon School, a college-preparatory school in Northfield, Massachusetts, as well as Boston University.
Short held a number of senior management positions in the digital advertising and marketing space at corporations such as Digitas, BBDO (formerly Ross Roy Direct), and NW Ayer. Short was Chief Marketing Officer of Charles Schwab Corporation from 1995 to 2000.
Short joined AOL Time Warner in 2003 as Executive Vice President of Brand Marketing.
In 2004, Short was a founding partner, business development lead, and Chief Marketing Officer of Product RED, a charitable organization created with Bono with support from the Bill and Melinda Gates Foundation.
Short became an angel investor and founded LotLinx in 2012. Short is the founding Chairman and Chief Executive Officer of LotLinx, which provides marketing automation for the automotive industry.