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Pierce Leonard has a diverse work history, starting in 2013 as a Head Counselor at Kieve Wavus Education, Inc. Pierce then transitioned to being an Account Representative at Carahsoft Technology Corp. in 2013. In 2014, they joined Aon Risk Solutions and served as a New Business Analyst and later as a Broker in the Financial Services Group. In 2017, they became a Professional Liability Account Manager at AHT Insurance and a Director of Risk Management at Scope Realty. From 2018 to 2020, they worked as a Senior Advisor to CoverStartups at CoverWallet, an Aon company. Most recently, they joined Assurely in 2020 as the SVP, Client.

Pierce Leonard enrolled at Culver Academies in 2007 and completed their studies there in 2009. Pierce then pursued a Bachelor of Arts degree in History at The University of the South from 2009 to 2013.