Tiffany Cheshire is the new assistant principal of McDougle Elementary School.
The Chapel Hill-Carrboro City School System made it official this week.
Cheshire served as a principal intern at Seawell Elementary before heading to the Alamance-Burlington School System as an assistant principal. She also spent four years in the Orange County Public School System as a Spanish teacher.
Cheshire received her Master of School Administration from UNC and earned her bachelors degree from Appalachian State.
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One prominent local businessman is being honored at both the regional and national level for his achievements in the financial services field.
Corporate Investors Mortgage Group, Inc. Senior Mortgage Banker Robby Oakes has been named to the Scotsman Guide’s list of Top 150 mortgage loan originators in the country; he ranked at no. 74 in the United States and took the top spot for the Triangle area. The Scotsman Guide is considered the most comprehensive list of mortgage originators nationwide.
In a written statement, CIMG Chief Executive Officer Jeremy Salemson says, “In addition to Robby being our company’s leading producer, he continues to distinguish himself on both a local and national level. Robby credits his success to his strong work ethic, attention to detail, and the tireless efforts of his support team. Robby also provides incredible leadership and inspiration throughout our organization.
Oakes has been a member of the CIMG team since 2003, and he was also named to the Scotsman Guide list in 2011 and 2012. He has local roots, graduating from Chapel Hill High School and UNC.
In addition to his Scotsman Guide honors, Oakes was named one of the top 75 mortgage originators in the country—and the top originator in the Triangle—by Mortgage Executive Magazine and National Mortgage News.
For more information on CIMG’s services, click here.
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