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Aschley Jolly has a diverse work experience in the field of risk management and underwriting. Aschley is currently working at Gray as a Corporate Risk Manager. Prior to that, they worked at Tempur Sealy International as a Senior Risk Management Analyst and later as a Risk Management Analyst. Before that, they were with Tower Hill Insurance Group as an E&S Underwriter I and Account Underwriter II, Account Underwriter II, and Account Underwriter I. Aschley also gained experience as a Summer Intern at Lloyd's of London.

Aschley Jolly earned a Bachelor's degree in Risk Management & Insurance from Eastern Kentucky University in 2015.