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Annissa McCaskill of Dutchtown South Community Corp.

This February, Employment Connection is celebrating Black History Month by honoring local leaders in the St. Louis region. Today we recognize Annissa McCaskill, Executive Director of Dutchtown South Community Corporation.

Annissa is a 26 year resident of the Greater St. Louis Metro who has served as Executive Director of Dutchtown South since June 2021. She is a graduate of Historically Black College Livingstone College, where she received her Bachelor of Science in Political Science. Annissa also holds a Master of Public Administration degree from Indiana State University. While at Indiana State, she was the first African American elected to serve as President of the M.P.A. Student’s Association and the first African American to be nominated by the university for the prestigious Presidential Management Fellowship. After earning her M.P.A., Annissa then matriculated at Washington University in St. Louis School of Law, where she distinguished herself as a member of the Black Law Students Association and as a Housing Law Summer Associate at Legal Services of Eastern Missouri.


After leaving Washington University to pursue a career in Urban Planning, Annissa’s efforts to succeed in her chosen field were fruitful. Beginning as a Planner I and then rising to the position of Assistant Director at the City of Chesterfield, Missouri, Annissa oversaw projects ranging from zonings, site development, updates to the Comprehensive Plan and Zoning Ordinance, and managing Zoning and Property Maintenance Code violations. In addition to her work at Chesterfield, Annissa was the first African American to serve as Planner for the City of University City, Missouri.

In early 2011, Annissa transitioned to the non-profit sector by joining Better Family Life, Inc., first as a Division Manager, then as Operations Manager, and finally ending her tenure at BFL as Vice-President of Workforce Development, a position that was created for her. At BFL, Annissa was responsible for budget management for two regions and oversaw case management of approximately 32% of the Temporary Assistance for Needy Family (TANF) recipients in the State of Missouri. During her tenure, BFL’s two service regions ranked #1 and #2 statewide in client engagement for the entire state.


Prior to joining Dutchtown South Community Corporation, Annissa served as Director of Residential and Commercial Development Services for the City of Belleville, Illinois, the largest city in Southern Illinois. In this role, Annissa advised the Mayor, department heads, and City Council on issues pertaining to housing, land use, economic development, zoning, and other similar matters; directed commercial/residential occupancy processes; created, directed, and implemented development strategies in conjunction with public and private sector groups, while also managing inspection activities. She is the first African American to hold this position. She has earned membership in the American Institute of Certified Planners of the American Planning Association but is currently inactive.

Following the example of her parents, Annissa believes her work should be one of service that forwards the greater good of all. She is a sister, a friend, an advocate, and the proud mother of M.R. Micah Clay, a student-athlete completing his senior year of high school.


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