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Brady DeSantis began their career as a Commercial Lines Account Assistant at Jones DesLauriers Insurance in June 2015. Brady then moved on to Allianz Global Corporate & Specialty (AGCS), starting as a Mid Corp Senior Underwriter in August 2016, and later becoming a Senior Underwriting Analyst in July 2020. In April 2023, Brady joined Navacord as the Vice President of Underwriting Solutions.

Brady DeSantis completed a Bachelor's Degree in Engineering from The University of British Columbia from 2010 to 2015. Brady then pursued a Master's of Professional Studies (M.P.S.) in Insurance Management from Columbia University School of Professional Studies from 2022 to 2024.