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Ryan Caulfield has a diverse work experience spanning over several years. Ryan began their career in 1999 as an Executive Chef at Restaurants Unlimited, where they worked until 2011. Following this, they joined Dino's Gyros The Greek Place as the Director of Operations for a year. In 2012, they became the Executive Chef-Operations at Cossetta, Inc., where they worked until 2016. During this time, they also held various roles at Levy Restaurants, starting as the Director of Culinary and later becoming the Assistant Director of Operations. In 2019, Ryan was promoted to the position of Director of Operations at Levy Restaurants.

Ryan Caulfield attended Cretin Derham Hall from 1992 to 1995, where they did not pursue a specific degree or field of study. Then, in 1996, they enrolled at Saint Paul College and completed a Culinary Arts program, although no specific field of study is mentioned.