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Penny P. Wickey has had a diverse range of work experience. Penny P. started their career at Bank of Boston in 1979, where they worked in multinational commercial lending until 1981. Penny P. then moved on to Harvard University, where they served as the Director of Finance and Administration from 1981 to 1984. After that, Penny worked as a Commercial Real Estate Agent at RAND Real Estate Services, Inc. from 1993 to 2004. Since 2004, they have been a Principal and Broker at Saugatuck Commercial Real Estate LLC, a full-service commercial real estate brokerage company. In this role, they represent clients in leasing, sales, and investments. Penny holds licenses in several states and is nationally certified as a Woman Owned Enterprise.

Penny P. Wickey completed their Bachelor of Arts degree in Latin American Studies at Smith College in the years 1971-1975. Penny P. further pursued their education at Cornell Johnson Graduate School of Management, where they obtained a Master of Business Administration (MBA) degree with a specialization in International Business from 1977-1979.