T
eresa Fleming scuffed her red bottom shoes (designer Christian Louboutin holds a trade- mark on the red soles) within an hour of wearing them for the first time. But instead of
getting upset—who could blame her?—she decided to wear them the entire next day. “You can’t take it with you when you go,” she said, as she strode into one of three maintenance facilities, her prized ankle boots leading the way. Fleming, the deputy chief operations officer for The School District of Philadelphia, channeled Rocky Balboa, the fictional Philly favorite son who trained for the fight of his life. When the day came to compete against undisputed heavyweight world champion Apollo Creed, Rocky’s goal was not to win but to stay on his feet for all 15 rounds. Fleming has the same drive, determination and heart. She doesn’t back down from challenges and confronts her own insecurities.
Fleming was raised in the small town of Manning,
South Carolina, but always had big city dreams. She moved to Atlanta, Georgia, at age 17 to attend DeVry University and graduated with a bachelor’s degree in computer information systems two and half years later. A couple of years later, she moved to Philadelphia, a city she’s called home for nearly a quarter-century. The City of Brotherly Love is where she raised son Hashim, who turned 30 last month, and where she became a fan of the Philadelphia 76ers. And it is the city where she is responsible for getting students to and from school in, which is no small task as the district transports over 23,000 students to and from 700 schools each day, often through narrow and crowded city streets that do not easily accommodate traditional buses. Fleming started her Philadelphia transportation career as an analyst in 2016, a year after receiving her mas- ter’s degree in business administration. The position required her to understand the various fundamentals of transporting students as well as the business of working closely with vendor partners. A little over a year later, she transitioned into the role of director of vendor services, a position she held for almost five years. Then, in Janu- ary 2022, she was promoted to the executive director of transportation services, and she leaned on her experience working with vendors, which represent a large part of Philadelphia’s operations. Between alternative trans- portation companies, cabs and yellow bus contractors, the district utilizes almost 20 vendors to help transport students to and from school. “It allowed me to build a solid foundation of under- standing alternative transportation, transporting general education students as well as students with special
52 School Transportation News • NOVEMBER 2023
needs,” Fleming said of her vendor experiences. She noted that she applied for the executive direc-
tor role because of her commitment to the students in the City of Philadelphia and the importance ensuring that students have access to their education. “And then my commitment to our department, we’ve had some turnover in just the few years that I’ve been here, so just being able to offer some more stability in that role and foster others new to our department,” she said. This past March, Fleming was promoted again, this time to deputy chief operations officer. She is respon-
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