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Cailyn O'Donnell-Assid, MBA, currently serves as the Director of Accounting Operations at Obsidian Insurance Holdings, Inc. since April 2020. Prior experience includes the role of GAAP Accounting Manager at Aspen Insurance Group, where responsibilities encompassed managing accounting for US program business and overseeing summer interns. Cailyn has also held various positions at The Hanover Insurance Group, including Financial Analyst II and Senior Financial Analyst, and served as a Senior Accountant in Accounts Receivable & Program Accounting at Aix Group. Early career includes roles at The Hartford and Vision Financial, focusing on accounting, financial analysis, and customer service. Cailyn holds an MBA from the University of Hartford and a Bachelor of Science in Management from Keene State College, along with additional studies at Sonoma State University.