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Colby Hewitt has a diverse work experience in the insurance industry. Colby began their career as an intern at Benfield in 2004, where they focused on treaty reinsurance. In 2006, Colby joined The Andover Companies as a Personal Lines Underwriter, and later transitioned to the role of Commercial Underwriter. In 2012, they were promoted to District Manager, overseeing a team of employees. Colby's most recent position was as the Chief Marketing Officer at The Norfolk & Dedham Group, a role they assumed in December 2017.

Colby Hewitt, CPCU, AIAF, ARe received their education from Middlebury College, where they graduated Cum Laude with a degree in English from 2001 to 2005. During their time at Middlebury College, there is no information provided regarding any additional degrees or fields of study.

Prior to their college education, Colby attended St. George's School from 1997 to 2001. However, no specific degree or field of study was mentioned from this institution.

In addition to their education, Colby Hewitt has obtained several certifications in the insurance industry. Colby achieved the Chartered Property Casualty Underwriter (CPCU) designation from the American Institute for Chartered Property Casualty Underwriters (AICPCU) in February 2008. In October 2008, they also acquired the Associate in Reinsurance (ARe) certification from the same institution. Furthermore, in May 2010, they obtained the Associate in Insurance Accounting and Finance (AIAF) certification from AICPCU.

Colby Hewitt currently holds the status of CPCU in Good Standing, according to The Institutes, which was obtained in December 2020.