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Jon Wollman has extensive experience in the lending and insurance industry. Jon started their career at HEMAR Insurance Corporation of America, where they held the position of Vice President from 1990 to 2006. In 2006, they joined ReliaMax Surety Company as Vice President, where they played a key role in the company's growth, overseeing operational, portfolio management, and business development aspects. During their tenure, the company expanded its client base to over 500 and achieved more than $3 million in revenue. Wollman's most recent role was at CURevl, where they held various positions including Chief Product Officer and Chief Operating Officer. As Chief Product Officer, they were responsible for developing and enhancing student loan programs for credit unions and mitigating program risk. Jon later took on the role of Chief Strategy Officer, contributing to the overall strategic direction of the company. Jon continues to work at CURevl.

Jon Wollman obtained their Bachelor of Arts degree from Huron College, where they studied Education, Political Science, and History. Jon attended Huron College from 1977 to 1981. Following this, they pursued a Master of Arts in Teaching degree at Augustana University in South Dakota, specializing in History. Jon Wollman completed their M.A.T. from Augustana University between 1982 and 1984.