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Jeff Olmstead started their work experience in 1987 as an Assistant Vice President at Gilpin, Van Trump, and Montgomery. Jeff worked in this role until 1995. In 1995, they joined Patterson Schwartz Real Estate as a Broker/Manager. In this role, they provided leadership to a real estate sales center and managed a team of 50+ sales associates and staff. Jeff was responsible for recruitment, training, and development of associates, as well as financial and marketing aspects of the operation.

Jeff Olmstead has a Bachelor of Science degree with a concentration in marketing and economics from the University of Delaware. Jeff also attended Archmere Academy and St. Edmonds Academy, although specific degrees or fields of study are not provided for those schools. In addition, Jeff Olmstead has a Bachelor's degree in Business Administration and Management, General from the University of Delaware. Jeff has also obtained certifications including Certified Residential Broker, Certified Residential Specialist, and Graduate Realtor Institute from the National Association of REALTORS®.