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Penny Jackson has extensive work experience in various sales and managerial roles in the real estate and hospitality industry. Penny started their career as a Supervisor at United Life Services in 1982 and worked there until 1989. In 1991, they joined Silverleaf Resorts, Inc as a Membership Processing Manager and stayed with the company until 2004. Penny then joined Thousand Trails, LP in 2005 as Director of Sales Support and later moved to Equity LifeStyle Properties, Inc in 2008, where they also held the position of Director of Sales Support.

Penny Jackson attended Prosper High School from 1976 to 1980. Penny then pursued Business Administration and Management at Brookhaven Community College from 1981 to 1982. In 2005, they enrolled at The University of Texas at San Antonio and studied Paralegal for a year.