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Cliff Greenhouse has a strong work experience, starting in 1982 when they became the Co-Owner and President of Pavillion Agency. In 1998, they co-founded Nanny Authority, Inc. and served as CEO. In 2006, they co-founded Pavillion Group Payroll Processing and served as Chairman. Most recently, in 2015, they co-founded Greenhouse Insurance Agency where they hold the position of Chief Executive Officer. This agency specializes in various types of insurances and caters to a diverse clientele.

Cliff Greenhouse attended the State University of New York at Plattsburgh from 1981 to 1982, but did not complete a specific degree or field of study.