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Aaron Chernow has a diverse work experience. Aaron started their career as the Principal at Aaron Marc Chernow, Attorney and Counselor at Law from September 1994 to December 1995. Following this, they joined MEC Personnel Consultants as Vice President from December 1995 to December 1999. In 2000, they became the Chief Operating Officer at Brightwing, and later assumed the role of Chief Executive Officer in January 2005. As CEO, they were responsible for the overall strategic direction of Brightwing and managed the Executive, Finance, and Operational teams.

Aaron Chernow began their education at Cranbrook Kingswood Preparatory School, where they obtained their High School Diploma in 1987. Aaron then enrolled at the University of Miami from 1987 to 1989, focusing on Business. Afterward, Aaron attended the University of Michigan, earning a Bachelor of General Studies degree in Business Administration and Management from 1989 to 1991. Finally, they pursued their Juris Doctorate at the University of Detroit Mercy School of Law from 1991 to 1994, specializing in Law.