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Sterling Douglass has held a variety of positions in the past decade. In 2010, they were an F.Y.C.A.R.E. Instructor at the University of Illinois Urbana-Champaign. In 2011, they were a Bio-Statistician Intern at Fujirebio Diagnostics, Inc., where they created a massive database on Excel to pull data from all products to be used by all facets of the company. Sterling then became an Actuarial Intern at Towers Watson in 2012, and an Actuarial Analyst at Towers Watson in 2013. In 2015, they Co-Founded and became the CEO of Chowly, Inc., which integrates Restaurant Aggregator orders into the restaurant's current POS system. Sterling also founded and became the CEO of Nyx Technologies, Inc., a mobile platform that allows customers in a bar or restaurant to order and pay for drinks on their phone.

Sterling Douglass attended the University of Illinois Urbana-Champaign from 2009 to 2013, where they earned a Bachelor of Science degree in Actuarial Sciences.