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Shah developed a Business plan for ContextMedia at Northwestern with classmates Derek Moeller and Shradha Agarwal in 2006 to distribute health educational content to doctors' offices and waiting rooms monetized by ad revenue from pharmaceutical companies. ContextMedia grew revenues 2,965% from 2010 to 2015 to $63.5 million with Shah as CEO, ranking it as the 6th fastest-growing private company in Chicago in 2016. In 2017, ContextMedia rebranded itself as Outcome Health.
Investors in Outcome Health sued the company, Shah, and Agarwal in November 2017, claiming fraud and breach of contract. This followed a Wall Street Journal investigation published in October 2017 alleging that Outcome Health misled advertisers with manipulated information. In January 2018, Outcome Health announced that the lawsuit has been settled, with the founders reinvesting $159 million of their $225 million investment dividends back into the company. Shah resigned as CEO as part of the settlement but remains chairman of the board.