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Harold Kyle has had a diverse and extensive work experience. Harold started their career at Boxcar Press in 1998, where they became the President. In 2002, they joined Bella Figura as the President, where they were responsible for creating unique letterpress wedding invitations using vintage cast-iron presses. Currently, Harold is the President at Delavan Studios, a position they assumed in 2020. Prior to their role at Boxcar Press, Harold worked as a Bookbinder at Campbell-Logan Bindery from 1998 to 2000.

Harold Kyle completed their Master of Business Administration (M.B.A.) degree in Business Administration and Management from MIT Sloan School of Management, from 2014 to 2016. Prior to that, they obtained a Bachelor's degree in Studio Art from Carleton College, from 1994 to 1998. Harold also holds a certification in Supply Chain Design from edX, although the specific details of when it was obtained are not provided.