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Jay Webster has over three decades of work experience, starting in 1984 as Vice President/Sales and Marketing at Marrick Properties, Inc. In this role, they are responsible for the Sales and Marketing of new homes in various communities. Additionally, they served as President of the Board of Directors at Calvert Hospice from 2005 to 2011. From 1989 to 1999, Jay Webster was the Broker/Owner of Century 21 Jay Webster and Associates, Inc.

Jay Webster attended the University of Maryland from 1976 to 1979, where they studied Business. Jay did not obtain a degree during this time. Jay Webster also holds a certification as a Licensed Real Estate Broker from the Maryland Real Estate Commission. The specific month and year they obtained this certification are not provided.