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Gwendolyn Diggs is the Vice President of Head Start & Early Head Start at the Urban League of Metropolitan St. Louis. Gwendolyn has over twenty years of experience in educational leadership and administration.

Diggs began their career as an assistant superintendent of education operations for the Ferguson-Florissant School District in 2001. In this role, they were responsible for the district's educational programs and operations. Gwendolyn oversaw the district's curriculum and instruction, as well as assessment and accountability. Diggs was also responsible for the district's human resources, including recruitment, retention, and professional development.

In 2016, Diggs left the Ferguson-Florissant School District to become an educational consultant for the National Institute for School Leaders (NISL). In this role, they provided training to school leaders throughout the United States using the NISL curriculum framework.

In 2017, Diggs left NISL to become the executive director of educational operations for Jennings School District. In this role, they were responsible for providing training to school leaders throughout the United States using the NISL curriculum framework. Gwendolyn also oversaw the district's instructional programs and operations.

In 2019, Diggs left Jennings School District to become the Vice President of Head Start & Early Head Start at Urban League of Metropolitan St. Louis. In this role, they are responsible for overseeing Urban League's early childhood education programs and operations.

Gwendolyn Diggs received their Doctor of Education from Nova Southeastern University in Educational Leadership and Administration. Gwendolyn also holds a Doctorate in Education Administration from Nova Southeastern University. In addition, they have a Masters in Educational Administration from the University of Missouri-Saint Louis. Gwendolyn is certified by the Missouri Department of Elementary and Secondary Education as a Principal K-8, Superintendent K-12, and Elementary Education 1-8. Gwendolyn is also a Time To Teacher Certified Trainer.

Gwendolyn Diggs works with Quenesha Catron - Division Operating Officer St. Louis County, Cynthia Wilson - Division Operating Officer Workforce Development, and Paula Carey-Moore - Director of Housing. Their manager is Michael P. McMillan, President & CEO.