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Drew Monroe has held various leadership positions in the insurance industry. Drew started their career as President at HH&B Insurance from June 2007 to June 2010. In 2011, they became President at Prosper Insurance Group. Currently, they are serving as the Head of Operations & Technology at Evertree Insurance since November 2023.

Drew Monroe attended Old Dominion University from 2001 to 2005, studying Finance, General.