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David Andrew Dewilde has a diverse work experience spanning multiple industries. David Andrew began their career in 1995 as a Beer Department Manager at Demoulas Market Basket, where they worked until 2002. Following this, they worked at Coastline Aviation in 2001 as a Flight Instructor. In 2002, they joined Executive Flyers Aviation as a Senior Flight Instructor and remained in this role until 2007. Since 2007, David has been employed at Sentient Jet as a Flight Operations Specialist.

David Andrew Dewilde completed their education in a chronological order. From 1993 to 2000, they studied at Daniel Webster College and obtained a Bachelor of Science degree in Aviation Management and Flight Operations. Additionally, from 1993 to 1999, they pursued a Bachelor of Science degree in Aviation/Airway Management and Operations at the same institution. Later, from 2013 to 2014, they attended the University of Massachusetts at Lowell and earned a Bachelor of Technology (B.Tech.) degree in Computer Systems Networking and Telecommunications.