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John Cantalupa has extensive work experience in the insurance industry. John started their career at MPIUA in 1991 as a Supervising Underwriter and held this position until 2008. John then joined the Massachusetts Property Insurance Underwriting Association in 2005, where they held various roles including Supervising Underwriter, Underwriting Manager, and currently serves as the VP Chief Underwriting Officer. John'smost recent position began in March 2017 and they continue to work in this role.

John Cantalupa attended The Cambridge Matignon School from an unknown start year until 1988. John then went on to attend Suffolk University, where they completed their education in 1993. However, no specific degree or field of study is mentioned for either school.