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Dean Reynolds began their work experience in 1993 at Comair where they worked as a Maintenance Controller until 1999. In 1999, they moved to Executive Jet Management where they held the role of Director of Quality Assurance and Chief Inspector, responsible for maintaining inspection standards and liaising with the local FAA.

Dean Reynolds attended Winona Technical College from 1981 to 1983, where they pursued a degree in Aircraft Mechanics. Dean obtained an A&P certification during their time of study at the college.