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Pamela Reiss has extensive work experience, starting in 1983 at ADP, where they worked as a Control & Banking Manager/Project Manager for almost 20 years. In 2004, they joined The Milford Bank as a Branch Manager/Vice President, a position they still hold.

Pamela Reiss attended the CT School of Finance & Management from 2014 to 2016, where they obtained a graduate degree. Additionally, they have obtained several certifications. In November 2017, they completed the School of Commercial Lending program offered by the Massachusetts Bankers Association. In July 2011, they became a Licensed Mortgage Loan Originator through the NMLS. Lastly, they obtained a Notary Public certification from the State of CT in November 2005.