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Hayden McCalman worked at Harbor Insurance Company starting in 2011. Hayden worked as the Chief Financial Officer until November 2022 and then became the Chief Executive Officer/President. Prior to Harbor Insurance Company, they worked as a Regional Sales Manager at First Magnus Financial from 2005 to 2011.

Hayden McCalman obtained a Bachelor of Science (BS) degree from The University of Kansas in the period between 1996 to 2001. The field of study pursued by McCalman during their time at the university is not indicated.