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Drew Monroe

Drew Monroe

CEO, Evertree Insurance

Drew Monroe is the President and CEO of Evertree Insurance, where he leads with a visionary approach to embedding insurance solutions and streamlining operations for growth. Before Evertree, Drew founded Prosper Insurance and grew it into a 100+ person agency across multiple states before its integration with Evertree in 2023. Recognized as one of Virginia Beach’s 40 Under 40 and for leading one of Virginia Business’ Best Places to Work for five years, Drew is also active on several national insurance advisory boards. A lifelong Virginia Beach resident, he is committed to community service and enjoys golf, travel, and adventures with his two daughters.

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